40 Year Old Virgin Shows Us How To Ruin Any Chance Of A Second Date...(Skippy)

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40 Year Old Virgin Shows Us How To Ruin Any Chance Of A Second Date...(Skippy)
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[@sixteenleo]

Hi Everyone, Thank you So much for 400,000 Subscribers. I Cant Believe we even got here. Idk If we can get to 500,000 anytime soon but what a journey its been so far. im proud of each and every one of us, and hoepfully we can keep growing and bringing people to this CUL...CHANNEL...hehe...C H A N N E L.

[@privateemail9755]

You've never taken a Xanax and it shows lmfao

[@TheNicoleasia]

Congrats, Leo.

[@raghavsaran9463]

Congrats bro, I love your stuff, keep making bangers

[@Baldskiiz]

you deserve it and so much more, its hard to find a youtuber who makes you belly laugh

[@amyoung101]

Congrats 🎉🎊🎉

[@evillynn258]

I can tell she’s a parent. She’s got that patience one needs for a talkative 6 yr old lol

[@jankompos2330]

actually both act like 6 year olds but of course women choose to side with women ,nothing suprising really ...

[@specializedchemicals6669]

@@jankompos2330 yikes

[@jankompos2330]

if you delete one comment delete all coments ,makes no sense ....aiight social media junkies im out ,lets hope leo does something compeltly crazy like mockj at reality and sanity,woof woof woof woof .....

[@abayomipoole4423]

@@jankompos2330 I don't actually think she was acting like a young child if anything she reminded me of a kindergarten teacher especially with the comments she made like "You're so cute," and you're adorable and basically having a big or cheerful reaction to most things he did as if she were encouraging a child. I don't think the person who made that statement was siding with anyone especially because of their gender and it's confusing as to why you see it that way.

[@ibuprofenwmilk]

@@jankompos2330 You good bro?

[@MrsPervy]

he treats his dates like kids, comes there with crayons and games. all this feels planned like a birthday party not a date lol

[@bigyikes8698]

I certainly hope that’s not how he treats kids.

[@clariceyhy]

@@bigyikes8698 I hope that he never meets any children honestly 😧

[@LunarEleven]

True, but no child's attention span would have lasted more than 1 minute of the elaborate plan, they'd all be running around in the street on a sugar high from cupcakes as he tried to get them to choose a crappy activity.

[@calholli]

Girls think like children... he has her in the bag.

[@greatfairyof]

@@calholli 🤨🤨🤨

[@lacenleather000]

I'm sorry but Skippy is not this nice, bumbling innocent man. He steps right over women's boundaries, calls them names, thinks it's funny to gift out r*pe whistles, sends loads of texts when a woman doesn't respond and the list goes on. He's really manipulative.

[@HappyHyena99]

he really gives off Chris Chan vibes when it comes to woman :/

[@etherealsunny]

@@HappyHyena99 That’s what I was thinking 😧

[@HappyHyena99]

@@etherealsunny honestly the signs are there, I just hate people make a joke of it… 😳

[@helvete983]

@@HappyHyena99 I think the same too, especially after seeing the video he thought he'd deleted.

[@fashiharz8584]

Yikes! I didn't know that. I didn't know him before watching this video. He looks like a normal awkward man.

[@ThatSoonerGuy]

“It’s killing me that I can’t hug you” - He’s stuck in Middle school/High school and treats women as if they haven’t emotionally matured past that. All he could think about was touching her in some way, so he went for the cheap shot. I’m a grown man and he legitimately creeps me out. His “vibe” is always so off.

[@jackstraw4222]

he cant accept the fact that he left high school over 20yrs ago probably and wont hire a dating coach for something like that...

[@CamelCasee]

Autism and unlike you he never got to experience a lot of milestones normal people do, is it any wonder many are stuck in the past like that.

[@jeanmichellelaurent]

wHeReS mY hUg

[@sauronthegreat489]

I'm an autistic grown man and find him off putting lol

[@ronaldross1959]

@@sauronthegreat489 🤣🤣 he's like in his 50's now i think

[@inkymera89]

Can Skippy PLEASE stop treating woman like children? PLEASE! Also these women have the patience of a saint. I'd be out of there in a blink.

[@alwayshangrygirl463]

And this is why you're not in his video 😘

[@tiffanykim2773]

I think maybe that's why he has them on video lol so they'll be nice.

[@alwayshangrygirl463]

@@tiffanykim2773 he wants to post proof that he's capable of getting a date

[@inkymera89]

@@alwayshangrygirl463 Good.

[@inkymera89]

@@tiffanykim2773 that's a good theory.

[@Lifeng07]

Since she has a kid I think she sees him as a kid too, playing along, humoring him, going along with his nonsense. She's got pity for him. Aww you got a bowling ball in your car? How interesting. That is so sweet.

[@Uveraeth]

Yeah, she literally said bless your heart lol

[@SouthSideOdaiba]

Damn that’s an all time low.

[@josie3221]

@@Uveraeth yeah i don’t think leo realizes that “bless your heart” is kinda insulting

[@v.e.l.pianist7848]

@@josie3221 he's just that pure i guess...

[@james-mullen]

Ya, i can totally see that.. What a bummber, so sad. He just needs to try less... Damn all this 2nd hand frickn cringe!! Ouch!!!!

[@JustJ-Me]

If Skippy ever had a child or dated someone with a child think of how jealous and competitive he would be for the Mother's attention. He likely would resent that kid for taking the attention, affection and love away from him.

[@helvete983]

I think we can count out him having a child. But you are so right if he ever had a enough dates with a girl brainwashed enough to introduce this psycho to her child then OMG.

[@ichoosemysanity6467]

Sad part is it's a lot of guys who don't do this and are still single.

[@KillerDoh]

@@ichoosemysanity6467 “they’re” not confident enough to date so many people or are incapable of dating, you gotta put yourself out there

[@ichoosemysanity6467]

@@KillerDohincapable of dating?

[@jackstraw4222]

@@ichoosemysanity6467 im no expert on this but...all the mixed messages can be confusing when it comes to dating,there is really good reasons why to date and why not to even bother...

[@BH-2023]

As a Clinical Psychology Grad Student, even though Skippy terrifies me, I want to study him. Like, the amount of potential pathology this guy exhibits: 1. Possible Truman Delusion, 2. Possible Clinical Narcissism/Borderline/Histrionic Pathology, 3. Arrested Development, 4. Lack of Mentalization, 5. Attachment Problems, is just so flipping interesting; I could legit write my thesis on this dude.

[@silviahannak3213]

Respect you for going down the Rabbit Hole. He terrifies me a lot. You got it. Mental Health is a real Issue. I am just saying : Amber Heard. He really reminds me of a Person i once know. Who freaked me out. She was totally mentally disabled. Being older but her Mind was that of a Kind. She couldn't speak understandable. He might be on a different Level of it. It just came to my mind cause of the Experience i had with that Woman.

[@SindyJ37]

Id totally read that assessment

[@assasin616]

Please write it on chris chan. This guy is nothing compared to chris chan!

[@CamelCasee]

What about autism?

[@beatsbyelvis6890]

I honestly think he’s just autistic. not that deep.

[@jewgatsby3387]

Leo, "bless your heart" is the southern way of saying, "you're kinda dumb, aren't you?" Not flirting Lmao

[@JustJ-Me]

"Bless your heart" in Utah typically means "You poor thing- I pity you", "You poor thing, I feel sorry that you're not LDS (which in the LDS mindset basically means) you're going to Hell/aren't 'sufficient' ", "I'm better than you" or "You're a sad excuse for a human". I've never heard someone in Utah use this term that isn't LDS btw...

[@JustJ-Me]

I haven't watched the entire video yet, but typically it's not a term of endearment- just the opposite

[@lesdyxiatoo]

I was bout to say!! My aunt (on my mom’s side of the family) says that. It’s definitely just a polite and coded version of “oh dear you aren’t too bright are you, well intentioned maybe but…”

[@StoutShako]

It's the nicest diss ever.

[@JustJ-Me]

@@StoutShako Seemingly. I hate it. I've had LDS people tell me "Bless your heart" or "I'll pray for you" when I inform them or they discover I'm not LDS. It's gross.

[@LazyQahnaarin]

He treats dates like he's hosting a game show. "And behind door number one is disappointment!"

[@Chyna_Doll]

And behind door number two…. More disappointment, and regret.

[@Gchildwarrior]

Door 3 is his basement....and the bodies buried underneath it

[@kino_vel]

BEHIND DOOR NUMBER 3..... . IS MY WING MOM... and my belly button lint collection.

[@kopo7466]

Behind every door is disappointment, especially his bedroom door.

[@mertalawiscious2873]

He obviously thinks real dates are like all the fake reality show dates he's seen on tv ...like on bachelor ,rock of love,flavor of love,shot at love,bachelorette,I love new york. They always mix dates with stupid games or challenges or compettions

[@allisonr8262]

I love how he shows her all the things he planned but couldn't do "because you only have an hour" BRO, YOU WERE LATE. But he places the blame on her needing to go.

[@d1nesh._223]

This woman is an angel, hope she finds someone who well Isn't Skippy.

[@PushinDaCushion]

😂😂😂

[@fifiweebunkinz2760]

Skippy need to learn how to just go out for drinks, shut up, relax and just have fun. All this planning. I hate it. I'd tell him I need to go to the bathroom then call an Uber and leave

[@dynamopirate470]

He is so uncomfortable and controlling. He has to be in control of everything. He's a scary guy.

[@durtypan]

My dudes Morman they are scared of alcohol

[@CL-lx2pm]

@@dynamopirate470 Yup, the biggest red flag of all. It's only a matter of time before he needs to control who he's with next. Nope right outta that shit the second you notice it, folks.

[@ashleeerin1886]

@@durtypan he has an addiction to opiates

[@blobfishbubbles2810]

I dont mind planning, but make it loose. That way you have things to do, but you can adapt to whatever comes up or new ideas. Lmao watching him talk I physically cringe.

[@goddammitalana]

My god, skippy is literally one of the most intolerable people I've ever had the displeasure of being aware of.

[@korkmazzi1299]

@@girlysoap9031 he might have something a little off with him or he’s just really socially awkward and doesn’t know how to act

[@smolsnek3835]

He makes my face fall off

[@ebansansamuel3576]

Yes. Him and no neck Ed.

[@driley5004]

@@girlysoap9031 may i suggest watching his other vids on him...Skippy is seriously creepy.

[@helvete983]

I thought I couldn't dislike anyone as much as Big Ed, but with this guy it's neck and no neck.

[@morgue.dweller]

these girls are too kind. if I showed up for a date and the dude pulled out a video camera, I'd be dipping

[@morgue.dweller]

she was probably like, "well he probably doesn't have any subscribers. nobody will see the video."

[@Chloe-gu4cd]

I really don't get how Skippy can't see the problems with his own behaviour, people have been telling him for YEAARS. The date is so complicated, he spends so much time explaining it and barely lets her get a word in. I am TERRIBLE at socialising and dating but honestly watching these makes me pleased I'm not this bad

[@jackstraw4222]

its because his ego ,he thinks hes the coolest and funniest guy all the time...he sees himself as a nice guy and then cant adjust himself when it doesn't go to plan....but im no expert on this...

[@tristonloux966]

Dude shows up 40 minutes late, has a full day planned out, explains it for too long, gets like 40 minutes to actually do things. It will be a miracle if he actually gets a girlfriend acting like this

[@banditxavier2893]

Honestly, if a man is 10 minutes late, I would just leave.

[@allisoncastle]

I know. And Leo acts like he’s this amazing guy…

[@baileyspeltbeefy1768]

@@allisoncastle that bothers me so much... I really like Leo but it seriously bothers me and makes me question him because Skippy is not normal and is honestly not a good man or person and is a nightmare to any woman so it’s a red flag for me that that another man is supportive of someone like him and thinks he isn’t as problematic as he truly is

[@allisoncastle]

@@baileyspeltbeefy1768 Right!! Perfectly said.

[@alpacawithouthat987]

@@allisoncastle he’s obviously joking any time he says Skippy is great

[@fifiweebunkinz2760]

Why do I feel like Skippy would the kind of guy to get angry when their losing a game on a date? And say passive-aggressive things to the girl.

[@camille0826]

I went on a date last year were me and the guy played uno and I beat him and he got so passive aggressive and salty. Throughout the date it was very cringy and he reminds me of skippy. Safe to say there was absolutely no second date 😂

[@RaidenKyo]

ur a little obsessed with him, dude’s a weirdo and has 0 self awareness but why make inferences about him that are proboably not true 💀

[@venomg5799]

@@RaidenKyo huh?

[@lola-ve3bb]

@@RaidenKyo no one is, we just can say whatever tf we want based off of similarities to our own experiences why’re you pressed 😂

[@jankompos2330]

@@camille0826 thats too bad and what would happen if you lost,oh you z generation self eestem adults ,always put blame on one person only not on yourself ,if we played uno i would let you win just becuase im not winning im not charlie sheen

[@CHloE748]

You say everyone wants to see Skippy succeed… I don’t know about that. Unless he SEVERELY changes, I hope he doesn’t get a woman. He doesn’t deserve one. He sees women as items, he wants to own one. He’s been seen constantly him going off on women, like going absolutely nuts when he doesn’t get his way. He thinks he’s entitled to a girlfriend just because he’s “nice”, he’s is the most obvious “nice guy” of all time. Pretends to be sweet just to get in a woman’s pants, then freaks out on her when he doesn’t get his way. I’ll root for him if he ever becomes a decent person. Also he’s a creep, remember when he went on the date with the chick who didn’t wear a bra, she was obviously uncomfortable the entire time with him and then he just HAD to say something about how happy he was that she didn’t wear a bra.. gross

[@melindarivera6598]

After watching the part at 20:34 a second time, I realized she wasn't giving permission for him to hug her. She said "We can AIR hug." and he still went in for it. She also didn't say, "You're cute!" like Leo thought she said. Nope! She said, "You're good." after Skippy kept apologizing over and over again for stealing a hug. Wowza! Skippy!!! Chill man! I don't normally say this because I don't think it is ever really applicable, but in this case, it most definitely is! Skippy, stop man! You're trying too hard! Chill with the extremely desperate attempts for physical affection from a woman. The ironic thing about it is if you would stop trying so hard it would probably happen pretty easily.

[@DocBree13]

Exactly!!! It wasn’t adorable in the least - it was just the latest example of Skippy ignoring boundaries

[@buttsmackasmr6296]

Just because she was saying hes so funny or cute doesn't mean she likes him. She could just be saying things to make him feel good and try to keep things from getting awkward.

[@animaanimus8011]

Yeah, a lot of women are raised/learn socially that preserving peace and not hurting someone’s feelings is more important than asserting themselves directly.

[@DeeWhoaaa]

@@animaanimus8011 Especially when some men can get aggressive after rejection.

[@sarahbarabe8470]

It gave me pity vibes. I think she just feels bad for him.

[@InTheNameOfLife1]

100% she is just trying to avoid conflict. I’ve reacted similarly on bad dates

[@freewithnature]

That can create very mixed signals for the other person 🤔

[@WritersBlocked13]

shit doesn't look like a date, it looks like a supervised visit

[@ssbmouse6471]

I’m dead lmaooooo

[@SailorSlay]

🤣

[@lizziej72]

Oh my gosh this is spot-on and hilarious!! Maybe it was supervised by Mike the DJ!!!

[@mrthaimaster]

Haha golden made laugh behind my wirk counter.

[@Beximuzy]

Skippy should lean into his planning skills and get into Dungeons & Dragons as a DM. He'd probably be really good at it and find it fulfilling

[@primadonna2819]

We get to zoom through this and only watch the "highlights". This girl had to endure the entire thing. She deserves some kind of a medal!

[@kaelynnydia]

i can 100% guarantee that “bless ur heart” wasnt as nice as leo thought lmao

[@jeffreydorman8715]

"Bless your heart" translation: "You will forever be in the friend zone."

[@Blank-41]

Im 99% positive these are pity dates. They just feel bad for him, and it's almost as if Skippy is trying to fail, not win.

[@andrewcruz1931]

So with me being rejected I should feel better because at least it’s not a pity date like skippy ? Guess I’ll take that as a win for me ? Lol.

[@jankompos2330]

@@andrewcruz1931 finally a person who is not ass kissing leo and of course thinking with his own head,be careful ,braindead people in large crowd can do serious laugh cramps ,to me skippy is being kinda clumsy but he is not like justin example all cocked up and barking too much ,skippy more of a cat persona

[@someflipnotes87]

@@jankompos2330 my dude relax whit the essays you sound insane.

[@helvete983]

I have picked up from previous episodes that he tends to meet people from the church.

[@PeterParker-jh4nz]

100% i'd say if i was him i would just stop

[@finnyoak]

I knew she must have been a parent or a teacher with how she spoke to Skippy. It's that tone of feigning interest as to not hurt the feelings of the child...or in this case, manchild.

[@vojtapergl858]

You are so cute, you are the best. Do you wanna cuddle? Lets cuddle!

[@pl4gued0ct0r]

skippy reminds me so much of an ex-friend. He had a crush on me and asked me out on several occasions and i would reject him coz i saw him as a friend. He would constantly put himself down over it like 'you don't like me coz im fat' type of thing and it just got so frustrating but at the time i wanted to be nice, he was my friend and i would help him... or attempt to coz he wouldn't even try improving or taking my advice anyway. After a bit of drifting apart because i was getting angry with him he decides to ask me for a kiss... well not ask... beg. he couldn't take no for an answer so i severed ties and the last message was along the lines of 'oh, you didn't want to kiss me because i'm ugly' like i always though that no body could be as bad (maybe worse) than skippy but goddamn life is... something else.

[@ticiana911]

Oh my god, the same thing happened to me… I had this very religious friend from university and she brought me to a costume party once where I met all of her other friends. They were great, very nice guys, we had fun. We were dancing a lot, and one of her friends decided to ask me out. I told him that I have a bf and he like never cared. As he was very nice that day and my friend told me that he is a nice guy I didn’t stop answering him. I wasn’t really dating beforehand, had no idea about these Skippy type of guys. I told him that there isn’t any hope that we would someday end up together, but didn’t want to be rude so I offered help. He accepted my help and we were trying to find him a gf. After an ugly breakup we went to a party as friends, all of his other friends were there as well. I was in a really bad mood. When I said I will go home around midnight he was like I will walk you home. I said no. Then here comes the ‘plz stay a little bit and talk to me’, stayed, he tried to force a kiss and I said forget about it. It won’t ever happen, why can’t you understand that I just wanted to be your friend? I just couldn’t stand him anymore. Then he was crying that it’s because he is ugly and fat as well (he looks basically like Skippy) and that nobody wants to kiss him and if I let him kiss me maybe he would gain some confidence to pick up somebody. He was manipulative, he knew that I was in a really deep sadness and that I would help an other unlucky and depressed person. I let him kiss me. It was disgusting and I told him beforehand that memorise this moment as it won’t ever happen again. He was very happy and grateful and the next day he picked up a girl, but it didn’t lasted that long and after that… he was asking about my relationship status again. Didn’t respond.

[@christiansnaturestudio6599]

It's your loss though

[@christiansnaturestudio6599]

@@ticiana911 rejection sucks

[@xX-qw4of]

21:48 that's cap, Leo. he's a toxic, gross person, and I'm sincerely happy that he has no one romantically. there's a really good reason he doesn't, people have been telling him in the comments for years, HE READS THE COMMENTS, and he changes nothing. he's not supposed to be with someone. there isn't "someone for everyone"... that's bullshit.

[@gaylordtinklefairy7479]

... Who hurt you?..

[@music0cool]

And he borderline stalks women, some of his videos are seriously creepy. In one of them he shows up uninvited at night to a womans house and tries to force a kiss on her

[@Callimo]

@@gaylordtinklefairy7479 I dunno, if what x X is saying is true, then this Skippy guy needs to work more on himself before trying to hook himself to someone romantically.

[@AnnWahlquist]

@@gaylordtinklefairy7479 he's right....

[@DarthRane113]

Oh there's definitely someone for everyone. But 1 it doesn't mean you'll ever find them and 2 it doesn't mean they don't meet the needs of other people already too (not single)

[@TheNightdream11]

I love how leo gives him real advice. Nothing would turn me off more than being surveyed at the end of the date

[@Maki-00]

I hardly like surveys the end of a business transaction! A survey for a date is completely ridiculous!

[@TwiCaCaX]

i mean evaluation is good but not how he did it LOL

[@PeterParker-jh4nz]

Leo is a man of the people

[@PumaArg]

I feel so bad for that woman, I feel the need to run just looking at the date. She looks like she's thinking "I must scream and I don't have a mouth". I've had the terrible experience of meeting people like this and in MY experience, they were misogynistic insecure man children who tried to push people into a relationship or even sex acting like nice guys, victims of their looks, when in reality their looks were the best thing that they had. And in my experience, it's really hard to reject them because they manipulate you into feeling guilty or even make you feel in danger

[@Imagigirl]

I really, really want to see Skippy somehow end up on a date with a really assertive woman. Like I want him to turn on the camera, get like five seconds into trying to pull out his crayons and dollar store prizes and then the woman just flashes her spine and shuts him down immediately. Like "Nah man, we're not lawn bowling. We're going to Dave and Busters. Right now, Let's go." Don't even give him the time to sabotage himself. He starts going off next to the giant Pac-Man machine like: "So how would you say this date is going on a scale of 1 to---" "Hell yeah! High Score! Hey Skippy, I want to hit up DDR, let's see if you've got rhythm."

[@stefania5882]

So weird. Right when I read the "scale of 1 to", skippy said those words lol

[@kieleleron85768]

Skippy so self-absorbed he says "That's enough about me tell me what you think of me" If he wants a second date he needs to be genuinely interested in the other person

[@smolsnek3835]

He isn't, and likely lacks the self awareness and desire needed to solve this in this lifetime of his

[@helvete983]

He literally plans his dates around getting her into a situation where she might give him a slither of contact, a hug, a kiss, a signed contract promising a 2nd date.

[@ichoosemysanity6467]

@@helvete983 That's cringe af

[@TheSkullknight12]

Leo, why do we want Skippy to win? He doesn't want to win himself. He's going to be a self-sabotager to the end.

[@tiffanykim2773]

Because he's nice (he being Leo)

[@TriniGamerGirl7]

Exactly!

[@loveableheathen7441]

He's creepy as hell and clearly sees women as objects. I couldn't care less if he "wins"

[@TiffyVella1]

@@loveableheathen7441 I want the women to win, unless he actually dates someone who honestly likes him romantically and sexually. Then they would both win, and that would be wonderful. But he will never date the female version of himself.

[@mrpeach2023]

@@tiffanykim2773 Too nice tbh. Love the guy, but there’s times when you shouldn’t be so nice all the time. Especially with people like Skippy.

[@lindsayschmidt2177]

I just had an emergency appendectomy a couple days ago and just now discovered this channel and I’m laughing so much my incision sites are hurting. Think that deserves a sub.

[@nathanr4633]

Skippy is a beacon of hope for autistic and anxious people, and it’s beautiful. Every time I think my interactions with other people, especially the opposite sex, are very awkward I simply watch a skippy video and all my fears melt away

[@CamelCasee]

But he's a failure.

[@thevrifiedlosr]

​@@CamelCaseethat's kind of the point lol

[@internetfrnd6496]

Skippy just creeps me tf out. I'm glad he records all of his dates because then we'll have ample evidence for when he eventually snaps.

[@RodrickMarsMoon]

Right?! By this point, it's just speculative that how he'd snap 😖.

[@Mrs.MoonToad]

Hey Leo! In the US especially the south, saying “bless your heart” is usually not a good thing. It’s pretty much like “you ignorant dumb person” The date was over right there lmao

[@DarthRane113]

Shhh don't be giving away our southern secrets !

[@mollymcmackins8311]

"Bless your heart" = "You poor thing"

[@demorik6794]

Yep I'm from the south as well, def don't wanna hear that from my date lol.

[@firefly_the_rescue9308]

For me, (a Floridian) “bless your heart” means. “Aw, I don’t care but I’m gonna pretend I do.”

[@PeterParker-jh4nz]

it was over before it started i'm afraid

[@leadershiplfe]

100% convinced that Skippy is fake. There's no way a person could be lacking this much self-awareness and be so delusional. Has to be an act right?

[@driley5004]

I thought so too, but its not really an act. Hes scary.

[@phir77]

I agree, I've met people like that. I doubt its self delusion and more wolf wearing sheep's clothes.

[@bekkes7923]

I dated somebody exactly like Skippy (although, more attractive) and put up with all these kinds of behaviors because I was searching for someone “nice,” at really any cost. Can confirm, these unbelievable people walk among us.

[@jackstraw4222]

its not ,there plenty of videos of him doing this over the years with no difference in approach at all...

[@Toskrr]

I’ve meant men like this. It is very for real.

[@Thcotwo]

I can't help but feel that if Skippy had a little self awareness of his awkwardness in these situations he could really use that as something to break the ice instead of bashing his head on the ice itself

[@Cerridwen7777]

I thought she offered an "air hug" and he went full on bear hug. Her body language when he hugged her, and she smacked his arm lmao

[@StephanieBenson95]

Yeah, I heard air hug

[@Casxa]

Oof that’s even more awkward

[@spacedino91]

She is not into him she just being polite. She probably went on a date with him so he would stop asking her. Some people give people chances so they will stop getting harassed about going on a date with them. Like hey we tried I do not think this going to work.

[@v.e.l.pianist7848]

Although i know you're right... don't destroy my hopes of finding the right one like that... almost was happy there thinkin' "if he can land that, there's still chances for me"...

[@dynamopirate470]

She doesn't owe him anything either. This dude is so creepy.

[@ghoulishtoad]

Exactly Most women are told its impolite to reject and thats why theres so many goddamn Datelines

[@ghoulishtoad]

@@dynamopirate470 its true but the culture pressures women into saying yes or else youre a bitchy prude

[@marshmallowloaf]

@@v.e.l.pianist7848 If it's any consolation, I was a mostly single man for most of life. 20 years, nearly 21! The people I've dated in the past were casual I anything and barely went past being "More than a friend" so we called it off. It wasn't until recently my bestfriend became my girlfriend. I've been in love with her for quite some time and planned on confessing, but she did it before I could. I never really was a guy that was conventionally attractive, I was always opting out of social situations because of my intense anxiety and fear of intimacy.. But we made it work, and we're quite happy together. Sometimes, the strongest and purest love comes from those we already cherish and have a bond with. Despite our few awkward dates.. I'd say it's entirely possible for anyone to find anyone if they work on themselves. By that I mean, not being an overall jackass. I truly believe the only reason this man hasn't found anyone is purely due to both his reputation and his attitude.. As long as you be yourself, even if that you is childish or anxious, I'm sure you'll find the one. They exist and I'm sure you'll know it when you both start to bond, whether it be originally as friends or romantically.

[@gurgy3]

He bought a date a father’s day card. He BOUGHT. HIS DATE. A FATHER’S DAY CARD. What in the actual f is wrong with his brain?

[@AlexDayz]

Why does he treat all his dates like they’re kids? Every “activity” he has planned out sounds like something an elementary school teacher would do

[@invadernav3422]

Every time I think Skippy can't surprise me, and yet- I can't imagine myself in the place of any of these girls, I've got some pretty severe anxiety myself and struggle with voicing my discomfort. I feel like I'd just disintegrate into the floor from the inability to say anything but the intense desire to flee.

[@GreyCinnabons]

I've dealt with a guy similar to skippy once and have the exact same troubles as you. And yeah, that's exactly how it felt lol

[@josie3221]

yup same. this would probably make me have a panic attack. probably wouldn’t agree to it in the first place though.

[@chels11327]

Omg same and it sucks so so bad

[@Lathnor]

Hmmm as a man idk how i am to others. I am just myself i guess and try to get a mutual understanding of the other person and then basically having 50% conversations aka 50% me and 50% her. Mostly so we both get to know each other

[@vanesah7771]

I think its kind of scary how hes made his personality so normalized when hes actually so creepy and weird. I think we should stop promoting his character.

[@DarthRane113]

Literally no one thinks his behavior is "normal" not in the context of other people at least, it's "normal" for HIM but that doesn't mean it's normal to society. Its like that weird friend you have who does weird things and your just like yeah thats him.

[@cardinalcrone]

Not only are your videos funny, but you're super insightful and actually helping me with some of my problems. Didn't expect that from a Skippy video lmao well done

[@Smidgefishh]

I kinda like Skippy's date ideas, I think they're sweet. If my fiance did some of these things I'd be like "hell yeah!" but, then again, locally here we have nothing special to do. if we'd wanna do like, an escape room, actual bowling, cat café/anime café, shopping, restaurant etc, we'd have to travel very far. Sad lol.

[@danielshore1457]

Yeah but his dares are like not first date things it's a let's have a picnic date at the park as our 4th

[@trashraptor_exe8446]

"I don't have balls, I have soda balls" I hate my terrible hearing at times, I was going to cry

[@kaorishimizu1373]

I heard that same thing lol

[@SharkieOttark]

I heard that too!

[@judelagcao2090]

Or maybe just a bad joke that explode our goddamn Head.

[@AlatOnDemand]

I heard that too 😭😭😭 and I read this the same exact time he said it 💀💀

[@arikray7030]

Assuming Alvira is in fact, a young single mother in SLC, I can't imagine how hard the social pressures are and the judgement she receives from the lds and I don't doubt if she has mormon family they'd push her to go for exactly someone like skippy; momma's boy, approachable, and most importantly, (in)celibate. He is the perfect depiction of a mormon man in utah

[@sugakookies8063]

Uhhh I’m Mormon and literally everyone I talk to (specifically Mormon, in this instance), whether they be a young person or parent, does NOT want to date a man like this (or doesn’t want their child to date someone like this)

[@MiracleMorris]

I see what you did there with celibate lol

[@totallypurple97]

That's what I was thinking as well. The pressure on single women in Utah from the Mormon church is depressing

[@miad6160]

@@sugakookies8063 are you a Mormon in Utah? It seems different there. More extreme.

[@arikray7030]

@@sugakookies8063 that’s great to hear! I know some fantastic people who are ex Mormons but from my experience, Utah itself is a cesspit of backwards thinking, prejudice and misogyny

[@Logical_Chronical]

The issue is he always messes it up because he's insecure of himself. He always talks down about himself in front of his dates. He also at times is passive aggressive if he thinks the woman isn't into him because of how insecure he is.

[@hughmungous775]

I love how you put things into perspective man. I'm a woman so it's helpful to hear how a male honestly thinks about things. Especially on the relationship side of things. So true when you said that if someone likes you they will make time in their busy life to see you. I was a single mom working full time when I met my husband and he was a single dad working full time. We only saw each other for like five hours to a day once a week for almost a year. It wasn't much, but we made the time because we really wanted to.

[@ashleeerin1886]

I love her saying “so you have an hour” … I think one day Skippy is gonna snap and do something terrible. Being nice to these guys is not mandatory ladies DO BETTER

[@joethfc3]

So women should be mean to him because he's creepy and weird?

[@ashleeerin1886]

@@joethfc3 yes

[@issahumps]

@@joethfc3 it would at least make him aware, though for skippy it probably goes over his head

[@tiffanykim2773]

@@joethfc3 no no they should humor him 😬

[@tiffanykim2773]

@@issahumps someone somewhere said he is actually aware lol

[@koosh138]

I can't say anything about Skippy's charisma. The dude has had more first dates than I've had bots on dating apps.

[@FirstnameLastname-gr5kb]

I guess that's bc he's asking women in environments where they feel obligated to say yes? At least that's my guess

[@helvete983]

He has some minor celebrity so some date him for clout, and he is also a member of the LDS, I've noticed a lot of his dates he meets through the church and church events.

[@PeterParker-jh4nz]

Can't really call them dates when it's pity.

[@hospitable_ghost]

He's from Utah and Mormon; that puts a pretty serious difficulty cap on his ability to get dates. Don't be too hard on yourself.

[@deamanieday5868]

I would say they did it out of pitty tbh because MAN NO!!

[@mobiusstripper7279]

I love how a date with Skippy feels like a day at discount summer camp. Skippy is the overly explanatory camp counselor who's trying too hard because it's his first day on the job, and he's nervous around kids.

[@PumaArg]

Last time a guy asked me to rate my first impression of him I literally told him "Well right now I think you're asking unnecesary questions", got up and left. Worst part? he asked because I was telling him how he was se*ually inappropiate with me the first time we met. I has asked him not to talk to me. That is such an "uwu I'm so insecureee" nice guy question to me, TRIGGERING

[@jkaloko1567]

At this point, there’s no saving Skippy. He always manages to get dates, but don’t know how to make the date good or keep women around. I want Skippy to win and be happily in love with the right woman. But he’s not helping himself out by doing his usual stuff on his dates. Either he change it up and improve or he will get the same results and the cycle repeats.

[@tacthom]

Well said.

[@ichoosemysanity6467]

Without social media most guys can't get any dates period.

[@jackstraw4222]

why cant he hire an dating coach or get dating agent to set up dates instead of him trying to hit on random girls that have nothing in common...

[@Transdimensional]

AYEEE a Skippy episode, leo blessed us tonight. you already know what imma be doing for the next 30 minutes.

[@kevinfranklin7572]

If you were to look up down bad, your first example would be Skippy. I don't mean to be hateful but damn. He does getting the date right. Everything after that. It goes down the drain.

[@gurgy3]

Fapping wildly?

[@charly9149]

@@gurgy3 went for this, thx hahaha

[@WrongSideC]

👀which would be........

[@ilayda6024]

Lord forgive me for what I'm about to do

[@thornie123]

I would assume, when a girl says “you’re so cute” a million times, that’s not good lol. Something they’d say about a puppy is not a way you want them to describe you.

[@evitaietavir2096]

She distincty said "we can air hug" and I can't know if he heard her or not, but I'm kinda sure he did hear, and THAT'S why he apologized twice rapidly after bolting into her arms against her wishes.

[@jamesmcmackin8773]

Why does he always talk to his dates like they're his 9 year old daughter?

[@HealingSavage999]

😭😭😭😭😭

[@folddealfeal2740]

so true bestie, its making me want to give him a great wallop in the back of the head

[@mrscoolwhipp]

People need to stop agreeing to go on dates with weirdos just to avoid hurting someone's feelings 🤐🤐🤐

[@helvete983]

I fully agree. What are you doing tonight? JK :)

[@mintvelvet3351]

Normalize rejection!!!

[@ichoosemysanity6467]

It might be a Mormon thing. Trust me no one has ever felt obligated to date.

[@kopo7466]

Skippy is the literal real life representation of Lenny from Mice and Men, he literally smothers everything he loves. And he loves everything.

[@dontmakemegothere7904]

Man, Alivia seems so nice. I hope she finds someone great. She's got the patience of a saint.

[@bongy59]

I was laughing at his cringe until I realised that his dating life is 1000% more active then mine, now I've just hurt my own feelings

[@bdel80]

That is shooting yourself in the foot

[@theadventuresofemily_]

Same lol 🤣

[@squishish]

honestly it's because they pity him,, That's always the vibe I get. He's also made it clear he usually does not take gentle no's as an answer very well(even when a "no we're just friends" which is a universal rejection but he doesn't accept those either,,) so it feels like most of these women say yes and then use the date to break it off all the way. It's kinda sad

[@xen2125]

I’d rather go on meaningful dates, even if they are rare, than sit through dates where the other person is internally cringing lol

[@impulsiveman5901]

69th like

[@brigadierharsh1948]

Dating Skippy would be exhausting. He over-plans as if he is spending the day with a toddler and at no point ever shows any genuine interest in the woman as a human being. He will be single forever because he makes hanging out with him a chore and is incapable of providing emotional support to anyone.

[@jankompos2330]

and what do you prefer ,pretend to be in some relationship and end up like justin,is that better,my opinion its better to be alone than to have a person next you and feel alone ,get it?

[@soomysaleem351]

@@jankompos2330 Skippy is that you?

[@annazitzevancih3459]

I have watched all your videos and I am now rewatching them! I work from home and have no friends so I keep KZbin on 24/7 for company your videos are some of my favorite!!!! Thank you for being here I appreciate it!!

[@joanabandeira9566]

Skippy plans his dates like summer camp💀

[@bowechosqualler]

The moment she said "Bless your heart," i knew it was over.

[@esmaharris7035]

Skippy behaves so juvenile and dates much younger women that himself who are so mature. Not only is it cringey it's creepy 😵

[@bhnurse16]

I agree! This woman looks younger than me (28) and I wouldn't even go on a date with Skippy. I'm the opposite though - I'm dating someone younger but they're mature for their age so it isn't a big deal..can't say the same about this guy! Lol

[@parkchimmin7913]

Not surprised, apparently he’s a momma’s boy. He’s not looking for a significant other, he’s looking for another mom.

[@jackstraw4222]

hes already 43yrs soon he will be 50 and dating the exact same girls age range....

[@emilycasey1023]

I would LOVE to see him maybe get a dating coach to coach him during the dates 😂 The dates with Skippy are strange enough! Why not make it stranger but with a 3rd person 💀

[@asiamowbray9555]

Hi Leo I just want to say that I have a lot of mental health struggles and your videos have legit become a way for me to cope. I play your videos every night and they always make me pee my pants laughing. So thank you for doing what you do 🙏ur rly making a difference

[@andsuddenlynoodles3103]

As a fresh resident of Utah, I live every day in fear of running into Skippy Also, dating in Utah (especially Provo) just freaking sucks. Props to him for getting so many dates.

[@JustJ-Me]

I was born and raised here in Utah (Utah County even). It's gotta be a culture shock to be new here. I'm so sorry. I apologize for the Skippys and SteVens in this state. Utah is rough, especially if you're not LDS. It is beautiful as far as scenery though. 🤷🏼‍♀️

[@DantesInferno96]

Why does dating suck over there?

[@thebasedrealist2263]

@@DantesInferno96 not op, but I dated a utah person for a year.we went to a drink and painting thing in SLC and they didn't allow caffeinated beverages. Like I expected they wouldn't have wine since not too many people drink but you can't even have a fucking pepsi. Also everyone comes off as fake nice. No one seems sincere like fuck they might be but it all comes off as "bless your heart" type shit. Theres a fuck ton of domestic abuse and its a real obey your husband type culture.lastly google soaking ts what Mormon teens do instead of having sex.

[@DantesInferno96]

@@thebasedrealist2263 wait no caffeinated beverages? Wtf.

[@JustJ-Me]

@@thebasedrealist2263 Gross! You brought up "soaking"! Lol I didn't even know that was a thing until recently and I've grown up in UT my entire life. The LDS do have their own lingo and "ways around things" that could be considered "bad".

[@aquatiger8]

pro tip Leo: in the Southern part of the USA, "bless your heart" is the nice equivalent of "please get run over by a truck" I haven't finished the video, so idk if this was the way she meant it yet

[@JustJ-Me]

Haven't finished the video either, but in Utah it's typically not a term of endearment. Pretty much the opposite- one of pity for the other person.

[@aquatiger8]

@@JustJ-Me I definitely think she meant it as "oh, you pitiful man" 😅

[@thedrewdog]

I'm from Southwest VA, and I can vouch for this. Either that, or when they say "Well!" after you finish a sentence.

[@anasilva4034]

You can see by her face that what she meant was "oh, you poor thing". Sounded like pity.

[@MG-ol8hs]

tbh i knew skippy was f***ed at the beginning when she said "you're so sweet". Not what you want to hear on a date anywhere in the world lol

[@chefmommyful]

Loving the commentary. Makes Skippy bearable. Thank you for saying what I'm thinking

[@SK-wo2qg]

Yay!!! I love when you don't edit out the cursing lol really adds to the quality of the content. Ps congrats on 400k. Here since 30k!

[@TrashbashMan]

I have this feeling that Skippy is that dude that constantly sends random friend requests to women on Facebook using his real name and just keeps pestering them until someone agrees to go on a date with him. Then on date day he introduces himself as Skippy instead and what we see is the end result.

[@scottyb8392]

Leo, I'm gonna be real, I had a rough day. I wasn't even gonna cook myself dinner but your upload has given me that motivation I need to feed my damn self, do the dishes and take the trash out. That's not easy for me after a nine hour day. Thanks man.

[@tara-aapje.]

Proud of you, Scotty :)

[@saintsugoi]

hope you feel better soon, i’m glad you were able to do all your responsibilities

[@scottyb8392]

@@tara-aapje. :) thanks, that is nice to hear

[@MsDragontooth]

You did great today. 😊

[@frozenraspberries1552]

Fuck yeah dude! You killed it!

[@mazegirl89]

Ik you probably will never read this, but thank you so much for making me laugh and feel just okay. The last few weeks have been heartbreaking and your videos have kept me from feeling helpless. Tysm and I wish you nothing but happiness.

[@taer7097]

He spent so much time explaining this long date plan instead of actually spending time with her and doing something 😂…and on top of that he got upset at hearing he only had an hour left before she had to leave

[@ProbablyBees]

I think I've figured out why skippy goes on such weird elaborate dates. he sees every girl as his own manic pixie dream girl. every date is the complicated, quirky thing that would only impress a girl has blue hair and dances in the rain and lives in a fantasy those dates only work in movies

[@arsonlemonade4386]

As someone who is 1/3 manic pixie dream girl I would like to say that I am utterly repulsed by skippy lol

[@HaintblueRee]

He’s got a high concentration of rom com in his system…unfortunately there’s no vaccine for that😔

[@missydeyoreads]

This is kind of entertaining. I mean, watching Leo is always entertaining, but I'm referring to watching Skippy here. It's kind of entertaining and kind of terrifying. I get that growing up in a repressed religion and with limited social skills is tough. But at what point does Skippy have some personal accountability and culpability of his own? He really freaks me out sometimes, because he exhibits all the telltale nice guy things. Like in one video, if I recall correctly, a woman decided to leave the 'date' early' (I think the woman thought it was a friendly hangout), or I think she just said she couldn't stay out longer because she was going camping the next day or something, and then skippy lurked around her house only to realize that another guy he knew was meeting up with her, so she blew him off for this guy she actually liked, he acted so bizarre and made a point of telling them that they had his blessing even though he was clearly butthurt. He makes absolutely no effort to seek counseling or talk to anyone who can actually help him become more self-aware and develop better social skills. He's overconfident, if you ask me, and for all the wrong reasons. He is obsessed with filming his dated because his 5 seconds of fame went to his head with the original show he was on. He treats women like children. He's not that considerate, rather manipulative, and he is absolutely a sore loser. He is the type to tell a woman every day how beautiful she is and when she makes it clear that she isn't interested, he'll send her a series of text messages telling her how he's glad it didn't work out because he likes someone else and she's too promiscuous and so on. I don't know. I would just hate to be the object of his affections. Is he actually affectionate, or just trying to get laid? Or is it all for views? He just does not sit right with me.

[@impulsiveman5901]

Agreed

[@Casxa]

I get the same vibes. He looks like he has an extremely low self-esteem. It’s really not attractive. I hope he gets professional help

[@angelwings1979]

I agree! So many nice guy vibes. He has shown in the past he's a nightmare when he's rejected.

[@criticalsurria6773]

“For the wages of sin is death but the gift of God is eternal life in Christ Jesus”- Romans 6:23 “So if you confess with your mouth that Jesus is Lord and believe in your heart that God raised Him from the dead, you shall be saved.”- Romans 10:9-10 I share this message with you so you may be saved and have peace for all eternity. Have a good day ✝️❤️

[@yyaaii]

20:33 she actually said “We can air hug” Skippy mistook it as an invitation for a hug.

[@siennabarger1914]

Leo, Bless your heart is an insult. She insulted him.

[@RemyBeast]

Skippy is just out here reinforcing the fact that clout is more important than true happiness for a lot of people.

[@orangeninja8022]

I feel like Skippy got that bowling ball by accidently stealing it. Like he forgot he was holding it when he left the bowling ally, and didn't realize that he took it until he got home and saw it in the passenger's seat. Then, for a second, he was like, "Wtf where did this come from?" And then he was like, "I guess it's mine now." Don't know why, but I can see that happening... 🤣

[@Alex-xr6hs]

i imagine he also said "finders keepers" out loud to himself when that happened

[@JustJ-Me]

Those shaky hands just couldn't let go of the darn thing!

[@criticalsurria6773]

“For the wages of sin is death but the gift of God is eternal life in Christ Jesus”- Romans 6:23 “So if you confess with your mouth that Jesus is Lord and believe in your heart that God raised Him from the dead, you shall be saved.”- Romans 10:9-10 I share this message with you so you may be saved and have peace for all eternity. Have a good day ✝️❤️

[@helvete983]

I have a different theory. 2nd hand bowling balls are cheap, he probably picked it up at a thrift store or yard sale. Then plays in a park with soda bottles rather than pay for a bowling alley. The guy tried to pay with a coupon at an already cheap restaurant on one date (shame he was to dumb to realize it was the wrong restaurant) He begs for donations for his dates at the end of each video. The man is incredibly cheap.

[@FionavanDahl]

@@helvete983 I also thought thrift store. He's definitely the type to see a used bowling ball and think "I'd better get that in case I ever want to bowl!" and years later is trying to justify it sitting in his closet untouched.

[@aliciag1595]

Only recently found your channel and love it. Now I have a lot to binge watch thank you sixteenleo. Congratulations on 400,000

[@terellchapman8737]

I’m getting skippy to write my research essay the way he turned 1 sentence question into a 500 page explanation is mind drugging

[@FanFav101]

I wanna see a video from the women's perspective tbh. Dude is a flat out creep, and if he stopped treating his dates like 5 year olds and acted like a normal adult maybe he'd do a little better. 🤦‍♂️🤦‍♂️

[@sirbradfordofhousejones]

She’s way too cute/good for him, LIKES HIM ENOUGH, yet he still mucks it up.

[@uritje]

I'm pretty sure she didn't like him from the beginning, she's just too afraid to hurt his feelings

[@sirbradfordofhousejones]

@@uritje oh, I agree with you. I just mean he could’ve left with a happy tone of “I can try again,” instead of doing that stupid ranking/survey nonsense. He needs dates without conclusions- just do the date, say goodnight, and ask again.

[@TheGroanOfWind]

How is sixteenleo not over a million yet?? He works so hard and he's absolutely hilarious and cool!!

[@shannonchristie1244]

I COMPLETELY CONCUR 16😾....with age Ive realized the exact statement you made....if you keep Downing yourself and being negative about yourself it doesn't make sense for them to spend the time arguing with you that that's not who you are....IT STARTS WITH YOU..IF YOU WANNA LOOK GOOD START SAYIN YOU DO.....START THINKING IT....like the quote: WATCH your THOUGHTS FOR they become your WORDS WATCH your WORDS FOR they become your ACTIONS WATCH your ACTIONS FOR they become your HABITS WATCH your HABITS FOR they become your CHARACTER WATCH your CHARACTER FOR it becomes your DESTINY!!

[@heatherallen5521]

ngl skippy with a beard and relatively long wavy hair looks like he should be a lawyer with a strong cajun accent shouting "NOW I dO dEcLaRe"

[@thirtythreeeyes8624]

He'd probably have much better odds if he took that approach.

[@ChronicllyHigh]

I just spit out my pop laughing at this

[@LatinaChef1986]

😆😂🤣😭

[@driley5004]

hahahahahahaha ACCURATE. and the pinky ring tops it lmaooo

[@lesdyxiatoo]

I’d like to offer this nugget of context: in one of his videos (yes I’m a subscriber, I wanted to follow his progress but…) he mentions how he’s always wanted to be a host on one of those late night tv shows, interview celebs and all that. So with that in mind, his dates make more sense when you look at it from his perspective and humor the idea that life and especially dates could be handled like how one would interview celebrities on television at 1AM. Obviously it makes dating that much more awkward and uncomfortable but that’s the conclusion I’ve come to after learning that.

[@DarthRane113]

Interesting factoid, did not know that. Kinda wished I didn't because I ow anything about his life is pretty useless lol That said I actually do hope he finds a woman who's genuinely attracted to him. Not one who's pressured into hooking up with him. But I really don't see that happening with how he handles dates overall.

[@beepbopboop7727]

He does to much talking to host or interview.

[@annamariamazzola7486]

Thanks for the Good Advice at the end .I really need that

[@annazitzevancih3459]

I started rewatching all your skippy videos thank you for more of this amazing content!!!!!!

[@amyoung101]

This is so painful to watch. He truly doesn’t learn or grow with time 🤷🏽‍♀️🤦🏽‍♀️ Skippy’s cringe is real😳

[@tiffanykim2773]

Or maybe he just doesn't care 🤷🏽‍♀️

[@guillermohernanmedranoolme8100]

@@tiffanykim2773 It doesnt quit the fact that Skippy is a cringegod

[@camille0826]

I feel like if Skippy met Drunk Justin, it would be like an immovable object meet an unstoppable force

[@cozycasasmr4510]

I need to see this

[@ssbmouse6471]

This is a great idea

[@emmad9344]

I would pay serious money to see that happen 🤣🤣

[@AndyMush]

Batman V Superman

[@benp1664]

Who is Justin?

[@laffemoore3694]

Skippy was born to do those obnoxious internet ads that take 40 minutes to talk around the product they're selling without ever telling you what the damn thing is until the last couple minutes of the video 🤣