Skippy the 40 Year Old Virgin's Wild Origin Story - (I found Him At 25)

Skippy's origin story starts as you would expect...him delivering pizza.
The Origin Story of 'SKIPPY THE REAL LIFE 40 YEAR OLD VIRGIN' - (its wild)
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[@sixteenleo]

Hey Leo, Love the New Video, Just wanted to show support, your channel has taken me from the hole that i was in, and put me into a bigger hole.

[@samiamchowdhury]

Woooo!!

[@sixteenleo]

was trying out the super thanks lmao

[@meggy_eggy557]

Wooooooo!

[@thewhisperingdiva]

Woohoooooohooooo

[@SlyfyGummy]

Wait what does this mean

[@music0cool]

If I was that girl alone with Skippy far away up a hill and he starts asking if I "like kissing boys" and then says he "has something for me" and he "brought me up here for a reason" ....yeah I would be getting ready to fight for my life.

[@karla9319]

I was just thinking how scary it must’ve been for her to reject him up there!!!!! It’s dark and secluded

[@SUBM4CH1N3]

I would've had a panic attack the second I got behind closed doors

[@J_Clean_1996]

Hopefully you wouldn't be dumb enough to even hangout with someone like him? 🤣

[@xMorganbrittnyx]

Right...can't tell if he's a benign incel or a malignant one 👀🤣🤷‍♀️

[@genodedemon5109]

You have a really cute profile picture. What's it from?

[@keithhall3927]

He went literal decades with little to no character growth. Fascinating.It’s like watching a car wreck in slow motion.

[@TCFan25]

Except instead of coming to a dead end crash it's in loop

[@44Todder]

Exactly right. I believe it’s called “arrested development”.

[@DBZAOTA482]

It's what happens when a boy grows up without a father

[@Account-vx1gf]

He didn’t get better, he got worse

[@nataliemarlowe2516]

skippy is just a classic case of a mommas boy who was taught what no meant but not how to respect it

[@Naptosis]

He knows how to respect a "no", what it means, and why it's important to respect other people's personal space, he just doesn't care IMHO. He doesn't think of these women as people, they're just targets that he might be able to convince to pity-sleep with him. Unfortunately for him, even the astronauts in the ISS can smell his Eau de Desperatio from orbit. As soon as he thinks he's been rejected, he explodes on women verbally for having the audacity to be a human being with their own wants and needs. His whole light-hearted, awkward, nerdy, christian-extremist, persona is a front to poorly smokescreen his own creepy recordings of his obsessive pressuring of these women into sex.

[@nataliemarlowe2516]

@@Naptosis yeah that’s what i meant. he knows what it means but respecting someone’s “no” also entails not doing what u described, at least to me. if someone exploded on me for saying no, i wouldn’t say they respected my decision. ya know?

[@positivevibesveda]

@@nataliemarlowe2516 I agree with both of you! I think the other person was trying to emphasize that he knows *how to* respect it but just can’t be arsed to put that into practice. He probably knows how creepy he is tbh and since he doesn’t respect women, he probably would only stop if a *male* law enforcement officer gave him a warning. _all i want is for someone to stop him but i doubt he’ll pay attention unless they have power over him_ . if not, everyone else is just a “hater” in his world. i feel bad for the women, i’ve been there myself. not fun

[@shineydeathpony85]

@@Naptosis I agree with your point however when she mentioned twice(which she shouldn't have had to) that she didn't want to be filmed. If he respected no he would have turned the camera off for the moment and spoken to her and would have pushed her with comments like "but oh you are to cute" and so on

[@talloncusack]

@@Naptosis spot on. Thank you!! Too many people let full grown men get away with shit like this thinly veiled misogyny and predatory behavior, as if they shouldn’t know better- they should…there’s no excuse for bigotry and not respecting other peoples’ rights- and I mean people of all genders, races, identities, etc…that’s why they’re called ‘*human* rights’, ffs.

[@FOCS27]

Fun fact: that first date had good camera angles and such because it was part of a pitch he did for an MTV show about him getting dates and just being super cringey and awkward. From what I remember, MTV ultimately decided not to run the show (hence why this is the only "pseudo-episode" that exists), and Skippy has just been clout chasing since (hence the TLC episode, the staged court case appearance, and his KZbin channel which follows the original premise for his MTV show pitch). He's been in a constant state of clout chasing and relationship chasing since his 20s. Part of me feels bad for the dude because he's been doing it for so long, and it still hasn't granted him the attraction he'd hoped for.

[@strangerde2709]

This explains SO much

[@MarianaRosalesbaek04]

Omgggg

[@pepironi992]

OP “I’m gonna teach skippy about social skills and how to walk to women” Meantime OP is Indian and most likely hasn’t even been with more than 2 girls his entire life Female simply do not find Indian men attractive. It’s a sad fact but it’s the truth

[@shararm]

Thats why this started so familiar at the relation ship part 🤢

[@strangerde2709]

@@pepironi992 my brother in christ Indian people make up like 17% of the worlds population...clearly this is not the case

[@glossylove21]

So... He's ALWAYS looked 40. Yep, that checks out

[@doctorjellybelly]

came out the womb filling out his tax docs lol

[@booleah6357]

Legend has it he was born 40

[@Oceana-Crystal]

@@booleah6357 I came here to say this. 😂

[@booleah6357]

@@Oceana-Crystal hive mind powers activate!

[@Oceana-Crystal]

@@booleah6357 🤯🤯

[@TuxedoMasc]

Skippy is "watched too many Adam Sandler movies and expect to be able to get any decent woman while being slightly predatory and with out any character growth in the end" personified.

[@BabushkaKoi]

Accurate

[@TrillMurray]

Damn you're like the white Shakespeare. Unless you heard this from somewhere else, you have serious poetic talent. A truer statement has never been uttered, written, or exclaimed.

[@bohemian_dropout9642]

@@TrillMurray wait. Wym white Shakespeare?? Wasn’t he already a white British dude 😭😭??

[@pariahcarrey]

Never thought I’d hear Adam Sandler and White Shakespeare in succession

[@TrillMurray]

@@bohemian_dropout9642 what are you? Like the white Karen?

[@annarice9063]

I live in the same area as Skippy. Sometimes I wonder if we have or will ever cross paths. Recognizing the local landmarks is a little unnerving.

[@enricovangelderen6464]

Eliminate him

[@c4ketown675]

Terrifying lol

[@LFPPNGTN]

He's making us look bad

[@Naptosis]

If you see the bushes rustling, the sun glinting off of a camera lens, and the suffocating aroma of Axe Africa (Lynx Africa) and desperation run. RUN!!

[@ShunJ89]

You could be the lucky girl he dates.

[@ashleeerin1886]

The waitress harassment is so infuriating…. I’ve been a waitress in the past and I would literally have answered so passive aggressively

[@rossmore4682]

hey ther, would you pls answer my dumbass questions while being filmed for the prospect of a 50ct tip lol The nerve of Skippy to do this sort of crap, I couldn´t even bring myself to do it as a joke.

[@Gchildwarrior]

Me as a savage waiter: "I'm betting my tip that she is better off without you. Anything else you need?"

[@rossmore4682]

@@Gchildwarrior I´d ask him, if he considers 50ct a tip, what the shaft must be like

[@mikesmancave8833]

@@rossmore4682 Jesus I haven't finished the video yet. He only tips 50 fucking cents?!

[@harrietyounger6118]

Show Shelly some respect. You throw her across the room then you are cuddling up in to her seconds later. Shelly if you need help blink twice.

[@rossmore4682]

Yea, that´s not very nice, Leo.

[@harrietyounger6118]

@@rossmore4682 it's ok we got her back.

[@salamantics]

@@rossmore4682 i completely forgot about the bit at the beginning so when I read this comment I was like "wow I can't believe Skippy did that!! >:("

[@dakotarobinson4202]

Why do Skippy’s videos always look like the beginning of a found footage horror movie before stuff hits the fan? 😂

[@cityofmarigolds2982]

'Cause it is...

[@ciarakelly3056]

I am in awe of the fact that this man looks & acts the same now as he did 15 yrs ago

[@annanieznanow1788]

Still same virgin 😑

[@siddubois4753]

Fr

[@veronicalysyj9023]

Yeah seriously talk about no mental or emotional growth whatsoever!

[@madeliefynana]

Well some people are like that, purely because they are like that or taught that from their past environment/relationships or because of a certain condition. I just kinda feel bad for him, I don't think Skippy has any means for malicious harm, but he's just digging his own grave without even realising it

[@jimmypadilla3441]

consistency king 👑 lmao

[@MarshmallowCUPCAKee1]

It's very clear to see from the beginning, skippy gives off very creepy and desperate vibes! Asking creepy questions, filming the date, asking for physical affection, pushing boundaries... all of that is gonna scare off any woman! If he just went on dates with no expectation and just got to know these women and didn't film, I truely believe he wouldn't be a virgin to this date & would have had some success with women.

[@laurenc4138]

Yeah, this is the problem with the whole self proclaimed incel community (not sure if he’s part of it but he’s like basically exactly how those guys are) it’s not that he’s super ugly, he’s not bad looking, just kind of a normal looking if not semi nerdy guy. He’s not some monster who couldn’t get a girl, if he wasn’t such a creep! I’ve seen way more out of shape or unattractive dudes have stable relationships, or even just hook up, because they have normal personalities. It’s 100% his creepy personality and he’s just never going to get that. He’ll blame everything else, his height, weight, “nerd” persona, whatever- it’s none of those, it’s his attitude.

[@ShinyFood]

@@laurenc4138 i think his problem in dates its always about making the date so complicated, like just keeping it simple would work, without all those little games. also hes should listen more carefully about the other person, i always feel like the girls never say anything about themselves in the videos he's always talking about himself. at this point i think he doesn't even want to change he just brands his lifestyle. if only he'd work on himself socially more he'd have a chance.

[@Esiaa]

Exactly, major desperate vibes. He doesn't care about who his date is on the inside and if they are compatible. He just wants a relationship, period.

[@firvantavan2793]

And, this is obviously fake. So that might be part of the problem.

[@Mars-dw2zc]

im glad he's never had a partner bc that poor woman would suffer from his obvious misogynistic beliefs

[@ManderSchmidty]

My mom passed away on Wednesday, and I’ve been rewatching your vids for comfort. Thank you for making things a little easier without knowing it ❤️ You deserve at least 1,000,000 subs!

[@lillymurray8408]

I’m so sorry for your loss. I can’t even imagine how you’re feeling especially this weekend. I’m here for you ❤️ you won’t ever not miss her, but it will get easier. 🕊

[@misskuni]

I'm sorry for your loss. I hope you have people to support and care for you.

[@sourgreendolly7685]

So very sorry Mander 💕

[@ManderSchmidty]

It’s definitely been hard, but I have great people around me ❤️🌻

[@samirascarlett]

My condolences to you! My mom's 3 year heavenly anniversary is on Monday. It always sucks around this time and it's still sad but you will feel better eventually. *big hug*

[@Katz_Pajamas]

He'd rather communicate with his date looking thru the phone screen while recording and at times commenting about her to an imaginary audience as if she wasn't there. It's fμcking scary how dissociative that is. A planned ahead project w/prior consent would've been different, but to be on a date doing that it's just weird! He's beyond what a normal level of insecure would be.

[@MaryJane-tp3qd]

Maybe I shouldn’t have watched that movie review of “spree” before this

[@lillymurray8408]

His approach is extremely creepy and intrusive….. I would’ve asked him to drop me off after the first “have you kissed boys before”… what are we 15 and in high school?! Jesus. So creepy.

[@sehnisweet343]

yeah, that’s a real red flag....a guy asked me that on a date a couple years ago because i’d mentioned it was my second date and i told the truth and said “no” without thinking and he got even more creepy and pushy after that and so i just left lmao skippy kinda reminds me of his vibe

[@idontwantahandlethough]

Truth. He's straight up infantalizing (I think I spelled that wrong but google won't help me) all the woman he dates. He literally thinks that all he needs to do to not be a virgin anymore is to bribe her with ice cream or something similar. She's a grown woman, Skippy... not a child. Ice cream is _probably_ not the secret pants-taker-offer he thinks it is. I hate to say it, but this stuff is exceedingly common among Mormon men. That whole religion is so horribly sexually repressed that the men often turn into this stereotypical "nice guy" type of creep. And to make things even worse, the girls are taught to be receptive to misogynistic behaviour like Skippy's and never ever speak up if a man is mistreating them, which is really unfair to those women (and him too, I guess.. but tbh he's the last person's feelings that I'm going to care about right now).

[@rickoftherick4610]

It's a miracle Skippy hasn't written a manifesto by now. He also sounds like one of those "Akshually" types of people who think they are smarter than they are .

[@zodaxa6141]

Actually, the word is "actually" not "akshually".

[@Deadpool....]

When he does he's skipping the normal rounds & will pull up with them hollow point ones

[@elitereptilian200]

skippy will end up elliot rodgering one day..

[@FEED_ME_A_STRAY_CAT]

@@zodaxa6141 this akshually made me cackle lololol

[@damnedza9368]

Hey Leo, just heard you call yourself a solid 3 out of 10. You are a whole lot better than that, you're a sweetheart and I'm surprised you're not taken already because you're a catch. Keep up the content because you bring a lot of joy to others. Lots of love from South Africa.

[@kasibelle]

Yea, keep the crown up king!!

[@Aster_Risk]

Same. He's attractive, funny, interesting and has a pleasant voice.

[@jangucreates]

Wait Leo you didn’t really say this, can’t be!

[@idontwantahandlethough]

Seems like a really good-hearted guy. in my book that get's you at least 5 points; it's basically impossible to be kind and ugly at the same time 🙂

[@annavictrix]

Yeah, even if you don’t include his awesome personality, he’s way more attractive than I think he realizes.

[@Ciela887]

Does anybody else think Skippy filming his dates is a form of self-sabotage? Maybe he doesn't even realize it. 🤷‍♀

[@ezracullen6183]

OOOOOOO, that's actually a really plausible theory

[@kristofnagy9374]

That’s a valid point there. Twist, he makes it on purpuse, because he’s affraid to have sex

[@kronictonic]

Certainly a possibility

[@ChristinaFromYoutube]

Ive wondered about this because he is Mormon royalty. I know that sounds crazy but he is a Jessup Ive literally never heard of a Jessup without a wife (or 40 of them.) I think its his only way out of getting married.

[@andrewneblock4103]

I think there's a lot of mental health stuff going on with Skippy, and most of what he does is self sabotaging.

[@apallo.11]

as someone who's still a virgin at 21, its seriously not the worst thing in the world. when you have good friends you dont really need a relationship. if i wanna go on a date i'll just call up a friend and we'll just do whatever couples do minus the kissing. and i kinda like that better bc there's no commitment or cheating or invested emotions or entitlement or anything so i dont have to worry about losing them. or actually.. maybe im just ace/aro and dont realize it. either way, there's other things in life besides getting a partner and having sexy times. EDIT: STOP REPLYING WITH HOW MUCH SEX YOU ALLEGEDLY HAVE, COULDN'T GIVE ANY LESS OF A FUCK!!!! EDIT EDIT: i got into a relationship since i posted this and yea it's exactly what i expected it would be. and i still don't believe it's something i absolutely need

[@firvantavan2793]

Having a romantic relationship is NOT the same as having a friend minus the sexy times, dude. There is probably nothing that has a bigger impact on your day to day life than who you choose to be in a relationship with. A great partner will improve your life immensely, while having an awful partner will mess your life up beyond belief. Regardless, it is not the same as hanging with your friends. Not by a longshot. Maybe relationships isn't for you, and that is great, but you won't know about that before you have a good one and sees what it's about =)

[@PraiseCastiel]

@@firvantavan2793 You clearly haven't had a proper friendship before if you don't think one can just as easily make or break your life. People need to stop this attitude that romantic relationships are "better" than platonic relationships. Close and healthy friendships are based around the exact same love, mutual respect, comfort, closeness and understanding. The best people I've ever had in my life are friends, while romance has done shitall for me. Friendships are JUST AS IMPORTANT as romance. Im sorry you havent realised that yet.

[@apallo.11]

@@PraiseCastiel dawg u spittin!!!! platonic love goes so hard

[@pastelhotmess9299]

@@PraiseCastiel period!! Friendships are amazing

[@Safarichromosomeslol]

Virginity is heavily downgraded for no real reasons. Let people be whatever they want. I'm almost 25 and I'm fine living my life without being touched by anyone...or even dating

[@kotacaelum9428]

as a utah citizen; ur description of the old couple selling candy and a methed out person stealing the money IS a very utah situation. (we also have a lot of weird names, especially news casters)

[@HelloXiuXiu]

I knew a guy from Utah, who's name is Travelon Rainbow.

[@leviacronym6770]

Self-depreciation is a turn off for me. I don't need someone to be an "Alpha", super confident person, but they shouldn't be airing their insecurities around me 24/7. Skippy comes off super insecure, clingy, and cringey. These are things that most females do not like. Also, most of the girls Skippy talks to/goes on dates, act the same. They're being polite and you can tell they're trying hard not to appear a certain way on camera. These women can't even unwind and be themselves.

[@elvis4868]

The type of girls that would go on a date with skippy are the ones that are too nice to say no

[@annme_87]

"Do you like kissing boys?" Reminds me of a dude who was trying to push a conversation into sexy territory. Out of the blue, mid small talk this guy says "Do you like orgasms?" What do you think?! Also kudos to second date girl (super glad we got to learn the server's name but not hers). I would have gotten out of the car around the time I said "I hate cameras" and he just laughed it off. I also can't stop cringing over him bothering Callie. She's just trying to work dude. She HAS to be nice to you. Don't fucking push it. One last thing; I definitely think nameless date was so relieved when Mark showed up to be a buffer.

[@talloncusack]

Omg that’s such 15 year old boy energy, you’re right. They ask if you like stuff you either haven’t experienced yet, at that age, or that obviously nearly everyone likes because it’s the definition of enjoyable- like, “do you like pleasure?” Lmao what.

[@qwandary]

The 'Do you like kissing boys' thing reminds me of when me and 3 friends were walking through town after a night of clubbing and two men began following at a respectful distance calling me and the other AFAB friend cute and asking if we want to ditch out AMAB friend and get with 'real boys'. We burst out laughing and said 'We'll stay with our real men, thanks' and grabbed our friends they were trying to emasculate and drunkenly staggered off. I mean it was mostly in good fun, everyone was drunk and the guys themselves seemed to laugh it off and give up, but the fact they thought that sounded cool always confused me. I'm guessing it's based on the fact we still say 'bad boys' when referring to some men?

[@DeezN00tz99]

"want to play truth or dare" "i have a question but idk if i should say hehe/do you mind if I ask you something..." "what did you do today? them: I dunno if i should say *immediately talks about masturbation*" always the same stupid tactics to bring it into sex.

[@tez228]

@@DeezN00tz99 right!

[@danielbroome5690]

@@talloncusack it's a lot more understandable when you consider that those boys have zero experience in these matters and societally/socially have the burden placed almost entirely on them to move things forward and its awkward AF for them with that pressure. Ya SKIPPY shouldn't be doing it, but making fun of people with literally no experience is also dumb. People say dumb things when trying something new.

[@dentxhead]

"as a very mediocre to horrible looking man..." whatever, Leo, out here acting like you're not the cutest thing 🙄

[@harrisoncraven]

Leo is a fine ass man

[@TheCamSays]

I’m convinced that this old Skippy footage is just him time traveling.

[@Gchildwarrior]

And still repeating the same mistakes. 🤦‍♂️

[@PurplePatterson87]

Skippy, the master of holding you verbally hostage.

[@demaris7598]

Leo, I find it hard to believe you were ever turned down. You are a handsome, respectful man and I just think you're the best. Keep doing what your doing, we love it.

[@VanessaLoveCounselor]

Word.

[@ninjanibba4259]

Everyone gets turned down sometimes, he’s no exception

[@fooofoooad]

كك

[@fooofoooad]

ك

[@fooofoooad]

@@VanessaLoveCounselor كح

[@MetallicaKing48]

I think the biggest problem that he’s always had is that he just can’t simply be natural. He’s always trying to put on a face or a front, or he’s just being completely awkward in left field. He needs to be natural, comfortable, and collected. But I don’t think he has that capacity.

[@TwoBearsBBX]

i cannot imagine being a girl and going on a date with skippy, so vile 🤮

[@madeliefynana]

I get what you mean, but that's kinda too far man.

[@boop3260]

@@madeliefynana how is it too far? He's a predatory creep. Call a spade a spade man.

[@madeliefynana]

@@boop3260 Maybe because I have seen worse and more disgusting scenarios? I personally didn't think much of it, because this feels a bit more game than some other stuff. Maybe also because the way Skippy acts is so surreal and odd, makes me think there was a reason behind it and had not a lot of control but to eventually end up like this. Just feels like he's unknownly digging his own grave and just getting deeper.

[@boop3260]

@@madeliefynana just because he's not as horrible as some people doesn't mean he's not horrible.

[@marinasaurus]

@@madeliefynana As a woman, Skippy is absolutely terrifying. The way he feels entitled to a woman showing him physical affection is disgusting. I would not feel safe being alone with him.

[@E.M.Weddle]

conspiracy theory: Skippy murders all his dates and thats why we never hear anything about these women later. for real though, Skippy is mad creepy

[@nefarioussness]

That storage unit where he keeps the corpses is piled high and stinking now.

[@UnsaidWords95]

I just discovered a centipede in my flat that I then lost sight of. So I needed this video to distract me from a full-blown panic attack, thank you.

[@doctorjellybelly]

prayers for you 🙏 my mom was bit by a centipede in her sleep and that shit aint no joke. im still like qhat the fuck edit: idr if it got infected but she needed to see a doc and take some meds

[@aquatiger8]

godspeed, comrade. those things freak me out, too. hopefully you find it soon

[@NGC_290]

I'm so sorry. May you rest in peace. 😂

[@adeer87]

You still alive?

[@Mystiqa]

I think that the fact that he records his "dates" makes it more awkward/imposing for the women. On top of that he keeps insisting on hugging etc, while saying it's awkward. That makes it even more annoying. It's like he's making use of the "awkwardness" to push his agenda on the women. Somehow he figured out that getting women to reject him and then being passive aggressive about it by emphasising on the awkwardness after the rejection will still get him a hug or a kiss cuz the woman will be like "ah I rejected him already, just giving him a goodbye hug/kiss is not gonna change anything" and they just wanna get it over with.. it's actually very emotionally draining on the woman's part. Some women may feel bad about rejecting him and give in to the hug or kiss he asks for at the end of the "date" cuz it's a very menial physical interaction, if you think about it. But for him, it isn't. It's just like how sexual predators find satisfaction with slight touches/strokes or even just looking at non-sexual photos. The predators can always try to explain it away or play it down if the woman feels uncomfortable about it. In this case, he openly accepts that it's awkward of him to ask for it but he does anyway, hence making the woman feel bad about denying his seemingly small request after rejecting him already in a date where he has been seemingly "gentlemanly" enough to accept the rejection and still be "nice" to her after that. There's a whole lot of deep manipulation and planning going on. Meanwhile Mr. Skippy over here thinks he's been a fucking gentleman cuz he took the rejection like a "champ" and still treated her "well" and only asked for a goodbye hug/kiss and then proceeds to wallow in self pity about being rejected all the time 🙄 he has issues.. he needs therapy. He needs a whole reframing of his fucking mindset. Goodness.. 🤦‍♀️

[@rossmore4682]

Good post, worth the read. I would advise you use paragraphs though.

[@rossmore4682]

Good post, worth the read. I would advise you use paragraphs, though.

[@snooganslestat2030]

The tl:dr is hes extremely manipulative and uses peoples (but especially womens) default to trying to be polite/not offend people in order to get what he wants. The tl:dr of my comment - hes fkn vile!

[@Apples765]

Thank you for this. I saw this red flag too but didn't know if anyone noticed

[@northwesterncalamity]

hey Leo, just dropping by to tell you ya genuinely put a smile on my face. thank you for posting your lovely personality for us to enjoy 💗

[@JohnGalt916]

I always think he's such a genuine person. Like you can tell he's a sweet guy IRL.

[@sixteenleo]

I appreciate you

[@northwesterncalamity]

@@sixteenleo i appreciate YOU !! 🥹💗

[@smokeshow9637]

Ngl, my heart dropped everytime Leo said he was a 3/10 … I’ve been watching for quite a while, & I have held my self back from commenting this SO. MANY. TIMES. bc it’s embarrassing af 🥵 but Leo is a 10/10 x 10 ALL DAY LONG. & So much more than just a (wicked) handsome face!! He’s multi-talented, sexyintelligent, empathetic, HILARIOUS!, unique … I’d be stoked just to pick his brain & have a conversation with him!! His Brilliance is Beautiful, & it all shines through.. & If I didn’t sound creepy enough: this video actually had me jealous of pillHOE named Shelly 😂🤣 && THE COMMITMENT!!! Leo kept his arm around her the entire video 😭 I was cackling!!!! If he’s this attentive with a flipfloppin’ pillow.. then something tells me that the girl Leo ends up with will be The Luckiest, indeed. 💕

[@nazaninsoltanpour6254]

You're simping all the way through, eh buddy? 😂😂😂🤣🤣

[@wlammy4ever]

Co-signing the simp ❤️❤️❤️❤️❤️

[@laurapardoe5347]

I feel you here

[@Ashak2001]

We are in the same boat. He's very handsome and witty

[@Aster_Risk]

It's strange that some people just can't see what they have to offer.

[@cootachoo]

Exactlyyyyy. Confidence is key. I'm 5'8" and my boyfriend is 5'4". I've seemed to always date shorter guys but this one's my first love and I'm just so goddamned happy to be with him finally ❤️

[@talloncusack]

Hell you can even be self-deprecating, you don’t have to fake confidence necessarily. Just don’t use it like a tool to get things from people out of pity!!! What Skippy does, among other “nice guys”, is force his dates to have to make him feel better about it. “It” being his looks, or his stated low self-image, or his worry that they’re “out of his league”, or him not getting pussy from other women, etc. The problem isn’t that he is honest about that stuff, it’s that he isn’t!! He brings it up incessantly without being asked and tries to put women into the position of “proving him wrong” about being unattractive or whatever, which of course they can only do by showing interest, so either complimenting him or giving physical affection to him. That’s his goal, of course. He doesn’t care whether they’re actually attracted to him or not, or why they’re kissing him or whatever. Whether they truly want to or not, it’s the same to him. That’s why he’s a virgin- if he even is one and it’s not a lie at this point- and his whole act is far more sinister than many people seem to think.

[@geenhaaien]

i’m 5’4 (maybe 5’3) and i really like this girl who’s 5’3 and yesterday she made a comment saying her preferred height is 5’10, what would ur thoughts be?

[@spectre9340]

@@geenhaaien well, do _you_ have a preferred height? Do you always date people of that height? If you truly get along with someone and are interested in them, it shouldn't matter.

[@geenhaaien]

@@spectre9340 i usually don’t care about height

[@geenhaaien]

@@spectre9340 my last relationship she was like 5’7

[@souup_]

Skippy sitting in a dark car like that, gives me such, "I'm going to strangle you if you don't date me."

[@Thomasonthesea]

Hey man I'm a new fan but me and my girlfriend think you're funny and honest about everything you do, and I just wanted to say you got another faithful fan over here, keep doing what you do man!!

[@troysparks3772]

Imagine hanging with Leo? I bet if he’s feeling good,it’s gonna be an awesome time shared with him. The video with hard rock nick is funny af,and that’s my favorite so far. But he got jokes for days for sure. Glad you 2 love his show. I do too. Dudes a riot! ✌️

[@pepironi992]

OP “I’m gonna teach skippy about social skills and how to walk to women” Meantime OP is Indian and most likely hasn’t even been with more than 2 girls his entire life Female simply do not find Indian men attractive. It’s a sad fact but it’s the truth

[@sere-san_5876]

Aw that’s such a sweet comments! I agree sixteenleo is so slept on I can’t wait till he blows up big, he properly deserves to!

[@MacassarMusic]

Skippy could use a date with a straight forward girl. Skippy: "Do you mind if I record the date?" Girl: "Actually yes, I do." Skippy: [explaining going from a friendship to a relationship] Girl: "Dude, stop. Just let things happen." Skippy: "Wouldn't it be nice if we kissed right now? We don't have to, but I'm just saying." Girl: "I'm not kissing anyone on the first date." Skippy: [speaking to a waitress] "Do you think we'd make a cute couple?" Girl: "Why would you even ask her that?" Although she'd probably leave at the first sign of creepiness.

[@Gchildwarrior]

She would have pulled out pepper spray if he lunged in for a hug

[@saram7889]

Skippy wouldn't be able to get a date with a girl who isn't afraid to say no

[@apurva616]

In the date with Taylee she actually said no to recording the date but he did it anyway. Several times, the women he’s on a date with tell him no or try to dodge his kisses but he kisses them anyway. Skippy doesn’t respect boundaries and it’s disgusting.

[@jeanmichellelaurent]

Tracy was pretty straightforward with how turned off, and creeped out she was with skippy

[@MichellePondueCruz]

If a guy brought his friend on a first date AND intended to film it, I'd question whether this was a date or a setup for amateur porn.

[@Gchildwarrior]

The sad, but funny thing in scenario 2 is that Skippy would be kicked out while they have fun

[@talloncusack]

I’ve never heard anyone pronounce “origin” like that lol but anyway…I’ve known about Skippy for years but didn’t know the whole local news hero part, crazy…! P.S… Also I’m pretty sure when she said something like “funny guys are hot and Skippy is hilarious”, she mumbled right before that “oh right I’m supposed to mention-“ meaning that was probably a line fed to her by Skippy or by that producer guy (Mark), and she was just making sure to say it before Skippy turned the camera off. I could be wrong but it plays out a bit weird. I wouldn’t be surprised if she’s a hired actress that this Mark dude arranged to date Skippy for the documentary they were working on. Also, Skippy is a predator who puts on an “awkward nice guy Mormon” front to mask his true intentions which are nothing but misogynistic and creepy and gross. Judging from his 15+ years of consistent behavior captured on film, I feel confident in saying if there were no consequences for it, he’d accept a child “bride” for himself. The reason he’s a virgin is because 1. SA is illegal and 2. Women can tell he’s not a genuine guy looking for a real, mutual relationship with them. It’s not that he’s awkward or doesn’t have game and doesn’t hVe good looks or anything like that- that’s what he wants you to think because then it puts it on women for being “shallow” or something. Really it’s because he is incapable of treating his dates as anything but objects of his desire, instead of individual people. He treats all women like they’re the same, and he infantilizes them by trying to bribe them for kisses with ice cream and shit. It’s really gross and other men falling for his act and making excuses for him, is getting old for me. Sorry just had to let that out for once. It might seem harsh but come on- what he’s put countless women through makes him deserve much more (in terms of repercussions) than my honest criticism.

[@angrymario8259]

That is a long ass Ps 😂

[@altoassassin]

I'd say that sums it up pretty well

[@TwoBearsBBX]

SAY IT LOUDER FOR THE PEOPLE IN THE BACK 🗣

[@AVspectre]

Yeah, I was thinking of adding a comment about pronunciation (suggesting OR-i-gen instead of or-I-gen) but it felt strange. I’ll leave a quick note here instead in hopes it comes across as helpful rather than critical. :)

[@cleobinx]

Yes , yes and YES!!!

[@zeldamae4540]

Another upload from our boy! Thanks for making the day a little bit better, one video at a time! Hope you're doing well, Leo!

[@SpookMeows13]

I fucks with the NASA shirt. My dad is an engineer for them. He worked on the Hubble Space Telescope! It's always awesome seeing people wear their shirts. Always makes me smile🥰 If you want more dope NASA shirts, my dad is the plug😂 I got you!

[@ArcadeAmbulance]

Yo?? What kind of dope shirts, I love NASA and ythe Hubble Space Telescope is one of the best things science has ever thrown out into the void. Kudos to your dad for his service to the scientific community the world writ large

[@wlammy4ever]

Omg im a big Hubble fan 😭 say hi to your dad from strangers in the comment section 😂😂😂😂

[@SpookMeows13]

@@ArcadeAmbulance He's very humble about it, but I know he feels real accomplishment. I'm really proud of him. He was a thermal engineer on it. He wasn't really a part of the James Webb Space Telescope per se, but he was working ridiculous hours managing and overseeing certain projects related to it. It wore him out, but it was certainly worth it. He's given me a few cool shirts, I have a James Webb sticker on my phone case he got for me and posters that I still have that he gave to me when I was a kid. He most recently gave me a shirt that basically shows the star map of everywhere the Hubble has been. It's super dope and I rock it (and the others) every chance I get! I love hearing stories about all he's done, and I'll never forget "bring your kid to work day" in elementary school. IT WAS SO COOL!!! Then, in that moment, even as a child, I felt so very proud of my dad. It's been that way ever since, 25 years later.

[@SpookMeows13]

@@wlammy4ever Please read what I replied back to the first person who replied to my comment. I think you'll enjoy that, too! I will most definitely tell him you said hi and that you're a Hubble fan!!! Thank you for saying something! I hope you have a wonderful day!

[@MaryJane-tp3qd]

I just bought one from Salvation Army and I’m wearing it 😂 I didn’t notice he was too ! I wish I could hit you up because my recently late grandfather made lots of aircrafts :)

[@Beardedbeauty33]

The first skippy date looks like a vintage snuff film

[@jeanmichellelaurent]

It probably was going to become one

[@daciagutridge7770]

He’s definitely giving me “virgin with rage” vibes…

[@yourlocalalien3790]

i agree when he said guys who constantly bring up their height are off putting. this goes for everyone, dont self depricate and bring up an insecurity to the point where it starts to get annoying, it really puts a damper on the mood. thats not to say dont have insecurities, most people do, but just dont make it your whole personality.

[@mightymeatymech]

Also, to quote Dr Seuss, those who care don't matter and those who matter don't care:) I wish girls would stop with the whole "6'0" meme but also, if someone is making those jokes about your height then do yourself a favor and let them go LMAO. They're definitely not worth it if they're gonna rag on your body! (Edit-- unless it's like a running joke with you two lol, I've had tall friends where we constantly joke about how short I am in comparison. Like leo said, context is everything)

[@anotherrandomdude1022]

Oh my freaking god, I felt sorry for this guy at some point, but I can totally see how awkward and pushy he can be sometimes, and this is off the limits I turned 26 today, still a virgin, and I really hope there is not going to be a moment in my life, when I'll turn into Skippy. It looks like he needs a therapist, hobby, friends or something. In the end, it's just too sad

[@jameer7565]

Even typing this shows you're self aware which is the opposite of people like Skippy.

[@HeyYouImAzu]

My man proceeds to take a girl up to look down at the city like every make out point in movies then proceeded to get real rape-y then proceeded to pull out his bath toys to write a children's book about relationships between navy personnel. How is my man not getting laid on the daily with such foolproof strategies?

[@Gchildwarrior]

Skippy: "It works 0% of the time, every time."

[@kidomaruking35]

This was a charlie moist critickal level comment

[@llcdrdndgrbd]

Because of the implications

[@Bleepbloopblarp]

Ok this is creeepy af! That poor girl was in survival mode, saying and doing whatever she could to keep him happy until she could get out of the car and NEVER have anything to do with him again. I don’t believe for a second that she would have any contact with him after that train wreck of a date.

[@tripleabattery2914]

Was just watching older sixteenleo videos the lord has heard my prayers 🙌🏾

[@sixteenleo]

Our lord and saviour nick crompton you mean

[@TheSaiyanPrincess89]

So for a couple decades now, he's been treating his dates like they're children. And that hasn't worked in securing him a wife? Is there no justice in this world?! DX For real though, is anyone really surprised that him patronizing women has led to him being forever alone?

[@BH-2023]

All jokes aside, the whole Friend-ship/relation-ship stick was soo unnerving

[@lumilenm__m5304]

So he's been trying for 15 years... Wow, I thought now that he was 40, he was desperate and grew impatient (not an excuse) and didn't gaf anymore but holy shit lmao wowza If only he had good genuine friends to help him out.. Especially when he was a young adult :(( Edit: Also, the way he's been obsessed with FILMING all the girls he's had a date with isn't just creepy, it's absolutely insane. U know he keeps the tapes forEVER. And yeah, if the date goes wrong, at least he has a video he can monetize. That's his "return policy", not taking the flowers away. But honestly, I'd rather him take the gifts away than whatever the hell this is.

[@JanecShannon]

Remember the other date he went on? Where he mentioned if it went well enough he was going to give her the keychain flipflop that lit up or something? *That's* why he didn't give her the flowers until halfway through the date. Back then he was still "testing" to see if the woman would be open to giving him what he wanted.

[@Julia-Ash]

Dear Leo, I’ve only came (this grammar doesn’t sound right….foreign ppl problems) across your channel about a month ago and I literally binge watched all your videos. I have never seen a more hilarious, more mature, and more talented gentleman like you. I’m a fan for life. Thanks for all the hard work. Much love from Chicago ❤️

[@n.howell8624]

I came across your channel only a month ago... I only found you channel a month ago. If that helps at all. I've is a contraction for I have, which I think is what was tripping you up a little. It sounds like you know more than one language. Grammar is a pain. You're doing amazing!

[@easyhair4health]

I'm from Chicago originally and also binge watched

[@cozycasasmr4510]

@@n.howell8624 there are grammar issues in your one tho 😅 there's nothing wrong with the way she said it at all

[@melitajay]

@@cozycasasmr4510 You can't use "I've" with "came" like that. You can say "I've only come across" but then that's present tense which doesn't work for this particular scenario.

[@red_menace1829]

You said it fine enough, tf do you mean foreign problems lmao

[@sxthconcreterose]

I am *so* glad that the youtube algorithm put your videos in my feed! You are incredibly charismatic and hilarious. I have no shame admitting I have been binging your videos and liking every single one in hopes it changes the algorithm for you. Everyone needs to see your vids and you deserve all the success!!!

[@heba8179]

As someone that's lived in Utah their whole life, I'm surprised he didn't just go to BYU. I just don't imagine him being above getting married after his first semester of college like everyone else that goes there

[@KZesty]

Oof that hit hard 🤣

[@cb6112]

After a brutal day in the rain at work i needed this laugh. I cant get enough of this guy. I've met soooo many people like him. So shallow

[@lachousalle31]

Do you push carts at Walmart?

[@cb6112]

@@lachousalle31 I remove hazardous trees.

[@barbthatsitjustbarb5680]

You've quickly become one of my favorite KZbinrs. I even go back to rewatch videos while I do things because it just feels nice to have someone talking while I cook or work in the garden. Your humor is absolutely spot-on for me 🤣☺️ thank you for another video!

[@IratePuffin]

I know it’s not their job but I wish some of these women who claim to be his friends would be brutally honest with him and tell him what he’s doing wrong. They all try to be nice but he’s beyond needing them to be blunt. “Skippy I know you’re nervous and I know you’re trying to be romantic and sweet but this whole thing with the boats is weird. It’s kinda a turn off. So is filming us on our date. It makes things even more awkward. Just relax and act like you would if you were hanging out with a friend, not a potential mate.” I think if they were honest with him he’d have gotten laid a long time ago. The irony is, he’s sabotaging his own chances at finding a girl who doesn’t get turned off by insisting on filming all his dates. He could still keep his channel going with other videos. He could date a girl a couple times before filming, then film a date if she agrees. It’s like he thinks the filming and the whole “I’m Skippy, the perpetual virgin, and I’m sorta famous because of it so let me introduce you to my fans” will attract a girl and he can’t comprehend that it’s super cringe and is a major reason none of his dates ever go anywhere. Someone needs to just get him drunk and hire him a “date.” Ffs, even Chris Chan did that to get it over with.

[@kittystetson6737]

Holy shnits, he does have Chris Chan energy 😳

[@Naptosis]

He probably not only doesn't listen (hence the filming, merch, and pressuring women still almost 20 years later). But they might even be afraid of him; he's got a vicious temper, has blown up on someone on video before, and has decades of pent-up sexual frustration and entitlement bursting out of every one of his pores, waiting to be unleashed on the first woman who can't escape. And look at what Chris Chan eventually did to the first woman who couldn't escape...

[@JohnGalt916]

Have you seen what happens to women when crazy men get angry? Remember Rhianna?

[@trashpanda3544]

The thing is people have told him what he's doing wrong but he keeps doing it anyway. He has addressed comments with these exact criticisms. He strikes me as the sort of guy who would respond with "well if they don't like those parts of me then they're not the one"

[@spectre9340]

@@Naptosis he definitely doesn't listen. There were a few dates where women would say they don't want to be filmed and he's over here filming them while asking them why they don't wanna be filmed. Consent doesn't seem to matter to this man. It's no wonder why women would end up feeling like they can't be more firm with him. 😐

[@totalmentemad]

Him: "I brought you up here for a reason!" - creepy smile My mind: Famous last words of a serial killer

[@iamthisiam]

Can you imagine that when he said he's going to wait to get to the restaurant to have the conversation, that he awkwardly sat in silence with this girl until they arrived at the restaurant and he turned the camera back on? Lol

[@thecolombian7536]

Skippy is the embodiment of "die as a hero or live long enough to see you become the villain"

[@MzGFunk]

I’ve had relationships but after around 30 it’s very different. I’m 33 now and I’m probably gonna continue to be single until I die lol. But saying that I’m not going to pressure people into dating me or being with me. Idc what the situation don’t ever do that to people. The fact that that even needs to be said is beyond me. Side note: The names... Skippy, Buddy.. probably some Champs and Bubbas lol!

[@MzGFunk]

@@michaelabraham8873 Thanks man appreciate the kind words.

[@adeer87]

You’re so young still. Don’t give up.

[@tellyourWiFiloveher]

Commenting this on all your vids I watch at the mo. I, a stranger on the internet, am incredibly proud of you. I love the way you come across, I see you, not your ego. I see how much you care about your channel and your viewers. I've seen the work you've put in. I get a warm fuzzy feeling in my tummy when I see you. Not in a weird way lol, like a proud Mum. Im 46, I could be your mum to be fair! 🤣😅 So just know, I see the work, I see how much you care, I love the way you come across on vid. You do you, bro. Because you are pretty fantastic. I will continue to watch your journey x

[@JennaLeigh]

What an incredibly sweet comment! The internet can be such a vile, toxic place that genuine kindness is refreshing. You're so lovely, Rachel- hope you have a great day ❤️

[@justlaura7177]

Man, your takes are always so wise and thoughtful. I appreciate your compassion and how you see the best in people. Also, you need to stop dogging yourself on the looks. You're in no way a 3. You're a good looking man with a great heart and amazing sense of humor. Keep it up!

[@ChernobylObsidian]

“YOURE GORGEOUS AND I ADORE YOU” lol your insight and perspective is invaluable, I hope others follow even half your advice. I appreciate you and your content. 🙏 thank you

[@95toutie]

Leo’s videos are my favorite part of the day 🤙

[@IzzyStardust]

"There are no super hero pizza guys" Peter Parker is fuming

[@jordannadroj9061]

I went bald in my 20s which made me even more insecure than I already was. Owned it and made it my thing, started dating again and met the love of my life, never been happier.

[@VerucaMarie]

I've been with my partner for 20 years (this October) and I've learned that the best way to keep both yourself and your partner happy is to constantly help better one another. You should lift your person up not drag them down. You grow and learn together and that is what shapes your whole relationship.

[@user-gx1cd5fo2w]

Sorry Skippy, But you make me feel ok. I sometimes compare myself and my life to the people I think is doing better than me.. and then I am sad... But when I see this, I feel like I am doing just fine and Even great! So thank you Skippy, for being eccentric..

[@Gchildwarrior]

Skippy is so inspirational that nobody wants to be like him

[@banditxavier2893]

The other day I saw a time lapse video of plants growing. Avocados take a lot longer to grow than potatoes. Some people are potatoes and some people are avocados. You just have to do your best and never stop growing! I think that's what happened to Skippy, he stopped growing.

[@user-gx1cd5fo2w]

@@banditxavier2893 wow, that was a good analogy or how its spelled.. thank you for that! Yes, I agree... And I tend to se a trend in very religious surroundings.. they stop evolving.. speaking from experience, not from people I dont know anything about.. But my mind thought of this when you said that.. its like when they only rely on one text and discard all else, cant go into our shadow side without thinking its evil or from the devil etc... The growth is stifled.

[@ninjanibba4259]

Hearing Avril “Complicated” in the background while Skippy is being weird is the DEFINITION of a red flag lol

[@elvis4868]

Goddammit I love that song and avril whyyy skippyyy

[@kazuyahirako4843]

That smile at 13:45 is something you'll see in your nightmares. Lol

[@tubblebub]

I'm totally with you - I want to sit opposite my date when at a table. I think it's super weird to see couples sitting on the same side when they're by themselves.

[@funnyvanessafunny]

Leo, that's a good video, as always! But you saying that you're not good-looking and a 3/10 doesn't show the way that I (and most likely others) see you! Obviously, we're watching for your content, your commentary, your jokes, your personality etc. because this is what this channel is about. You make the commentary both fun and interesting which is just incredible. However, I also think that you're really beautfiul & handsome, much better looking than what you probably think yourself as! (And I'm sure others agree...) Of course, it's not everything & you're allowed to your own opinion but I just wanted to make sure to tell you my own! You absolutely deserve to be told that you're beautiful!

[@N1ght44]

YEAH LEO FLY AS HELLLLLLLLLLLLLLL he's probably being humble, speaks a lot about his character

[@sarahharrisginge736]

He's damn fine - looks *and* personality

[@YesDutchess]

He's joking calling himself a 3/10

[@_dreamscape]

Right like I’d do anything for a leo to date

[@sarahharrisginge736]

@@_dreamscape same! But I'm *actually* a 3/10. I'd love to meet someone like him one day though. Men like him are rare af

[@KirstenlyArt]

Awh Leo, youre definitely not horrible looking. You have a fairly symmetrical face, your features are well positioned and proportioned, your facial hair grows in solid, and its well groomed, you have fluffy hair, you have a brilliant smile and a very nice nose, well-shaped nose. Objectively, you hit most of the marks that are used to define attractiveness in human men. Have more faith in yourself!

[@ahshitherewegoagain7461]

As an artist, he is lovely to look at.

[@__m__a__x__]

Whoah, Detective Leo needs a raise for unearthing all of this!

[@sere-san_5876]

Tbh I think his mom hyped him up too much as a child. My little brothers like this, my mum always tells his he’ll break so many hearts and date so many girls cause he’s just so HaNdSoMe I feel like Skippy is someone who took that to heart and is now just confused to why women don’t like him. It also maybe proves why he doesn’t change his attitude, he was told it’s perfect and took it to heart. Moral of the story, don’t hype your kids up too much. Luckily my brother has me to tell him what a dumb shit he is. Like literally girls in his class have come up to tell me what a dumbass he is. Someone needs to get something through that skull

[@Amtoro]

Love you Leo, but I have to massively disagree - Skippy freaks me out. I would honestly feel in danger if I found myself on a date with him. (edited for spelling error)

[@laurenc4138]

Agree, to me he’s terrifying, like it feels like all of this has something kind of sinister right under the surface. Like one time a girl will say no and instead of being an awkward weirdo trying to save face, he’ll go full nutcase and become a legit stalker. I feel like his mannerisms, his actions, what he says, it’s all barely concealed disdain when these women don’t immediately put out for him or confess their attraction to him/won’t immediately be his gf… It’s just so so unnerving. I’m honestly surprised he hasn’t crossed a way worse line because he feels he’s owed sex, based on his actions. His whole personality screams “dude on an incel forum claiming they do everything right but women hate them for no reason because they’re trash”. Like he constantly films women to try and make them be nicer or do things physically that they probably (definitely) would’ve not done if they weren’t on camera, he refuses to take no for an answer on almost anything he wants, he ONLY focuses on how “cute” or “hot” they are, it’s pretty clear he doesn’t see women he’s attractive to as human beings- just as potential sexual conquests.

[@marinasaurus]

@@laurenc4138 Yes. Truly he scares me. The questions he asks are so gross and predatory. He is pushy af.

[@laurenc4138]

@@marinasaurus agree! So creepy!

[@BarryManders]

Another timeless Skippy video and Leo, looking fresh to death. I will never tire of his work (musically and commentary, alike) and seeing his subscriber count grow brings me SO much joy. You deserve the world, Leo!

[@nachgeben]

No, he has the camera out because he thinks it'll force a woman to be more compliant out of nervousness.

[@spectre9340]

I think he does it so that whenever he "scores" with a woman, he has proof of it -- which is a really childish mindset. It's like when boys would brag to their friends about how they slept with a girl from their class. A classy man wouldn't need to show off to other people

[@threeraccoonsinatrenchcoat8863]

This dude is insane. Ive just found your channel. This is the first Skippy vid I've seen of yours. I'm not even done yet, he's at the boats as I'm typing. Dude is a psychopath.

[@stephanieking3113]

"I have something for you..." "What.." She probably thought she was about to be murdered lmao

[@StorybooksInn]

i wish he (and others) would understand that being a virgin means nothing. virginity is a social construct. it doesn't matter if you've had sex or not. who cares

[@0428733]

While I do agree with you in that being a virgin doesnt matter (well, at least it shouldnt). Calling it a social construct is stretching it a bit. Either you've been inside a girls guts or not. Sort of like saying eating is a social construct.

[@codyjoco]

In Skippy’s origin story he wasn’t just a pizza delivery driver, he was a driver for 5 Buck Pizza, the bottom of the barrel pizza in Utah. Home of unlimited toppings though! :D

[@rhuntern]

"Funny guys are hot!" "Really? Knock knock." "Who's there?" "Me." "Me who?" "Me who is picking you up for our second date." Idk, but it's better than trying to make her say he's who she was talking about or doing that weird dance about a second date LMAO

[@vidiyya]

Honestly this is one is cheesy but cute. I am already in a long term relationship but I am going to use it sometime soon. Thanks!

[@cfecrystal]

I was having a bad day but after I saw your new video, it bought a smile to my face! I love your humour and how fair you try to be on both sides when commentating, keep up the great work!

[@sweetfiredrawer77]

The sitting thing, I’m a very anxious person when a restaurant is full of people… so my bf for our first date he sat next to me because he noticed I was nervous and look down a lot🥺 so cute of him to sit next to me and held my hand 🥺✨

[@Samionigaming]

‘Sure you can have a hug’ = ‘please don’t murder me, Skippy’.

[@simisim0566]

The problem with Flippy, is desperation. He doesn't care about chemistry, doesn't care about comfort, he just wants to jump right in. Desperation is super unattractive.

[@juggalogamer8541]

Exactly he's just way too fast way too soon just tries to pressure women into doing stuff they don't want to do he's very self-centered and selfish when it comes to women it's all about his needs and doesn't care about the other woman it's like just be yourself have a conversation get to know a person no pay can you answer this question can you answer this question will you please kiss me please kiss me please kiss me please kiss me he constantly begs for everything like a little child no wonder this guy's a virgin he is the absolute word desperate

[@KoalaBerzerker]

This is like an alternate dimension where Chris-chan was at least half-succesful with the Love Quest.

[@opalwzrd]

Part of me wishes I could go on a date with Skippy to give him the rundown on how to act. The other part of me values my safety and wants to be nowhere near him.

[@mechveteran01]

I think you're the most genuine dude on yt Leo, and I watch a LOT of yt. Hope you're doing well man

[@veteranredbeard6222]

bro you really should do a "dating coach" segment with Skippy. I'm sure he'd be into it.

[@ardenalexa94]

Or he will learn nothing and think he’s doing nothing wrong. Which sadly I think is more likely

[@StephanieBenson95]

Can't wait til you hit 500k! I am once again asking... Where. Is. Fluffs!? 🔎🐥

[@leew.4987]

ya I miss Fluffs so much 😢

[@angelabernal4076]

Skippy reminds me of Tarantino's character in From Dusk til Dawn. The No Doubt playing in the background....very nostalgic

[@katielane2363]

Listening to Avril Lavigne and No Doubt while Skippy cringes us out is a real vibe.

[@CallMeKinky]

On behalf of Black women and femmes, we would like to politely decline your offer of Skippy. 😭😳

[@afterglcw5050]

😭😭 no woman or person should be in the romantic vicinity of skippy

[@StephanieBenson95]

Understandable. Have a nice day.

[@Gchildwarrior]

We already kicked him out of the virgin community. Don't return him to us!

[@sierrasmith773]

The first girl was probably scared cause he literally drove up a hill and asking creepy questions and ready to fight for her life

[@VictoriaJunmei]

Okay Leo coming from a 21 year old straight girl in a relationship you are not bad looking at all and with your personality you are AT LEAST AN 8. I don't think quantifying your attractiveness is gonna help how you see yourself because there's no way to convince anyone of something they don't see, but you are not bad looking and a great guy. Any girl will be lucky to be with you. Keep your head up king!