This might be kind of a weird problem. Actually, it might be several weird problems. They all kind of go together. I'm a twenty-year-old college junior in New York, and I'd like to become sexually active. The problem is there's no one who really seems to be knocking down my door, begging for the privilege of fucking me. The thing is, I'm pretty overweight—I still have an hourglass figure but with a lot of fat packed on—and an unattractive face. I'm a size 16 and a DD bra, and I've got small eyes and a huge nose. My questions are: how important is it to be in love with the guy you first fuck? Will I really regret it if I just get hammered and fuck some random guy? Will some random guy fuck me? Can I find that window in between being drunk enough to fuck me and too drunk to get it up? Also: what age is it old enough to get plastic surgery? I'm trying to lose weight, but I also want to have plastic surgeries to make my eyes bigger and my nose smaller. The thing is, my parents have led me to believe that they'd be hurt and upset if I chose to get plastic surgery to alter the facial characteristics I received from them, that it would be somehow rejecting them or something. The thing is, it has nothing to do with them. It has to do with the fact that I want someone to fuck me, and I want someone to want to fuck me. So what do I do?

Ugly in New York

Sent from the Savage Love App for iPhone

My response—and UINY's response to my response, my response to her response, etc., etc.—after the jump...

It's your face, UINY, you can do what you like with it. And one day your parents will be dead... so live your life, for yourself, while trying to be considerate of their feelings without allowing yourself to become paralyzed.

You used the U-word first so I'm going to run with it: there are ugly guys in NYC. Lots of ugly guys. Fuck one of them—drunk, sober, whatever. And since people rarely wind up with the person they lost their virginities to, UINY, the relevant question isn't, "Should I be in love with (the first) guy who fucks me," but, "Where do I find a kind-enough, considerate-enough guy to fuck me?"

And that applies whether you're a virgin or the whore of babylon.

Look around, get out of the house, make yourself as presentable and available as possible, and stop telling yourself that fat = unfuckable. Huge numbers of Americans are overweight or obese and most of them are getting laid. So keep your eyes peeled for someone in your league, maybe someone in your same situation, who is kind and considerate, and fuck the shit out of him when you find him without pressure, without expectations, without illusions—but with condoms, okay?

And... your face is your face. There are lots of plastic surgeons in NYC. Schedule a few consultations, see what can be done, price it out. Then if you decide to have work done on your nose and eyes—can surgeon really make eyes bigger?—inform your parents of your decision, emphasizing that you love them, of course, but also emphasizing that you're not asking for their permission.

Unless, of course, you're asking them to pay for it... in which case you will need their approval.—Dan

Yeah, whether or not they pay for it depends on—obviously—if they'd do it, but also if I have the balls to wait a few years. If not, I'll find a way to pay for it but that'd be really hard. And is losing my virginity to someone I then don't end up on necessarily good terms with going to screw me up emotionally? And should I have been in a relationship with them for awhile? Ack. And thanks for responding—I can't believe you're actually dealing with my shit!—UINY

Do you know any sexually active grownups? NO ONE—well, very nearly no one—winds up with the person he/she lost his/her virginity to. You want to find someone you like, someone you could maybe see yourself with if things worked out (someone who is relationship-quality, even if a relationship isn't in the cards), but if your standards are WE ARE IN LOVE and WE ARE GOING TO BE TOGETHER FOREVER, well you will never lose your virginity. Very few people would if those were the conditions people set.

Find someone you like, or could like, someone you feel like you can trust, someone you have a good feeling about, someone who seems like a guy who'll treat you kindly and with some tenderness, someone who seems considerate and into you. (Big girls with hourglass figures have their fans—get on some BBW sites.) That's the most you can hope for—it's the most anyone can hope for when it comes to their first time.—Dan

That's true. As the last virgin standing, I guess I've built it up to be something huge, where you're with someone for months and months and finally you realize you want to have sex because they're so amazing. Or...something. But I guess it's not always the case and even if it is, it isn't for me. Now i have to find the happy inbetween space between random club sex and a husband. Thanks, Dan—I really appreciate it. Your column and podcast are amazing.—UINY

Good luck, UINY. Trust your gut, find a nice, decent guy, be safe, use condoms, etc., etc. But get out there and live a little, okay? Rent Auntie Mame—be Agnes!—

Dan

You are my hero. Seriously.—UINY

LIVE!—Dan