I Lost My Virginity To Someone I Met on Tinder: Ask a Pro

By The Head Pro

The end times are upon us: A question from a bro!

Head Pro,

So I think this website is funny as hell, and I read it from time to time and figured it’d be interesting to get a third party’s perspective on the following.

Me and my buddy are both Pros. A couple years out of college, killer finance jobs, nice apartment, all that good stuff. We go out a lot and there isn’t any shortage of girls here in NYC. Long story short, we were introduced to these 2 girls by a mutual friend while visiting our alma mater a few months back, and we hit it off immediately. Fast forward to the present, and we’ve hung out and hooked up with them, and quite frankly, we both are a little more enthused about them than we had imagined.

For some substance, they are solid 10’s, and I do not use that term lightly. Awesome, down to earth, not sluts at all, just all around catches. Now the kicker- they’re only 20 years old. 

On one hand it’s refreshing to have girls who are more mature than their age and not just interested in my bank account, country club or when I’m getting a table at Lavo (typical NYC 24 year old girls). But the flip side to that coin is that my friends literally laugh in my face when I bring it up. The general perception (which if you had asked me 4 months ago, I would have agreed with) is that a 24 year old, good looking guy, who is entertaining the thought of pursuing a 20 year old clearly has something wrong with him.

So my question to you is this. Is it that weird? I think I'm just enthralled by the fact that I don't have to jump through hoops with these girls like is standard practice with girls my age or older. I know in 2 or so years that a 4 year age gap is pretty much nothing, and my stepmom is like 20 years younger than my dad, but I can’t help but think I’m asking for trouble even considering this.


Dear Mr. I’m too Macho to Say “Dear” or Make up a Cutesy Pseudonym,

Honestly, I think your bros are just jealous that you and your buddy are tapping a couple of hot 20 year olds while they’re stuck getting drunk and making out with chicks from HR at company happy hours. Dating someone that young obviously has a certain Matthew McConaughey in “Dazed and Confused” sort of appeal to it, but it’s not like you’re picking up girls at the school playground. They’re fucking 20, not 16, so I don’t see what the big deal is. Plus, even with your sweet finance jobs, you’re still too young to have accrued any real assets, so there isn’t really any gold for these girls to dig if that’s what your bros are worried about.

The only thing you have to worry about if you do decide to commit and get attached is the fact that these girls still have a lot of growing up to do. As mature as they may seem, think about yourself four years ago, or even two years ago. How much have your interests changed since then? When you’re in college you tend to become a “new person” every other month, because that’s just what you do at that age. So what I see as a worst-case scenario is if you, two pros with established livelihoods and prerogatives, fall in love with these 20 year old girls and then a month from now they decide they’re bohemian and want to date artists in Bushwick. That would suck. For everyone.

I don’t know you and I don’t know these girls so I don’t know the odds of that happening, but if you really like them I say date them all you want but don’t over invest. If, two years from now, when they’re fresh out of college and you’re closer to 30 than you are to 20, things are still happening, more power to you. I’m sure that’s what’ll happen, because if there’s one group of people who I know are in no way flaky, it’s 20-22 year old girls.

If That Doesn’t Work Maybe Try the Playground,

Head Pro



Dear Head Pro,

About a month ago I started talking to this guy on Tinder and it quickly became clear we only wanted to bang each other so we started Snapchatting our bits and pieces, and texting and flirting and finally we met up and well, it was a disaster.

This guy has a MASSIVE penis. I was a virgin. My friends told me I should find a 'starter size penis' but I'm almost 21 years old and I'd had enough of waiting. It started off great, making out, doing the things you do, but I didn't get much attention, so when it came time to put p into v I was not wet enough, but I was so preoccupied with the fact he tried to get away with no condom, it completely didn't occur to me to be like, we need lube dude. So long story short his massive shlong ripped my vagina, blood everywhere, had to go to the hospital, nothing allowed in my v for at least 2 weeks.

Now, while this sucked, I want to try again. He is not so sure. I've asked him a couple of times and he says he's worried its going to happen again and that he needs to think about it. He's had three weeks. We still talk, but not as much, and Snapchats are infrequent, whereas before they were everyday. I got super drunk the other day (i.e super horny) and offered to give him head and he accepted. But I'd done this before in my two weeks of hell, but he just kind of avoided it. Never said no, but was like, there are other days, I'm hanging out with the guys, etc.

What I would like to know is, is he playing me? Or like, is he so genuinely concerned that its going to happen again, he's avoiding as much sexual contact as possible in case he decides it’s too big a risk? I am just very confused and wish he would just tell me yes or no, and my friends are too nice to be like, give the fuck up and move on, so please be blunt.


Not getting any

Dear Not Getting Any,

Christ, I almost don’t want to touch this one. Seriously, what the fuck is going on in the world? First a guy emails me with a legitimate question, and now you, a virgin, decided a smart idea would be to have sex for the first time with a guy you met through a pseudo dating app who happens to have a dick shaped like a Pringles can. Why?

I know that your virginity isn’t necessarily some precious flower you need to guard with your life, but if I knew all it took to get laid were a couple of iPhone apps, that’s probably all I’d do all day every day. Oh, and let’s not forget this guy “tried to get away with no condom” the FIRST time you ever had sex together, and yet you continued to hang out and give him oral sex and are hoping to “try again.” Again, why? And not just why, but physically how were you giving this guy head if he couldn’t even fit inside of you? Fun fact, when handled properly the vagina can expand to accommodate whatever’s in it, up to and including a baby. Can you fit a baby in your mouth? No, you cannot.

This whole email kind of smacks of bullshit, but maybe you’re just young or something and kind of dumb and unaware of the way of things. In case it’s the latter I’ll proceed, because this is apparently what I’ve decided I’m doing with my life. Basically, he’s not necessarily playing you, but he’s definitely over it. As traumatizing as the vag ripping was for you (how you could even want to have sex again after that happening your first time is beyond me), it was also traumatizing for him, and not just because of the blood/unpleasantness. I’ve known or at least heard of guys claiming to have truly prodigious dongs like that, and believe it or not they’re usually very self-conscious about it. Sex is always difficult for them because of their size, so when this literal worst-case scenario happens, I’d imagine it’s incredibly embarrassing. Even if he knows it’s not going to happen again, he’s not going to be able to stick it in you again without feeling truly awful. I’d say to let this one go and “officially” lose your virginity to a guy whose penis doesn’t look like a baby’s arm making a fist.

It’s also possible that this guy is perfectly normal and you, being a virgin and all, were unaware of how even a normal sized wang would feel in your ladyparts. Either way, you should be fine in the future provided you never again make any (literally not one) of the decisions that lead you to this point.

Is it in Yet?,

Head Pro

PS is this him? 


Email the Head Pro at [email protected] and follow him on twitter @betchesheadpro




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