Tips for losing my virginity via online hookup
November 10, 2010 1:56 PM   Subscribe

Tips for losing my virginity via online hookup

Hello, I am a 19-year-old straight male who is a freshman in college. I am a virgin due to having gone to a single sex school and the college I go to isn't exactly one of the top party schools in the nation and most of the girls around here aren't that hot anyway. Therefore, I would like to try and lose my virginity via a hookup initiated online such as on craigslist casual encounters or another website. Any suggestions regarding websites, what I should and shouldn't put in my profile, the likelihood of success of this whole venture, etc. are what I'm after. Please tell me everything you know and think I should know.
posted by anonymous to Human Relations (47 answers total) 4 users marked this as a favorite

Hmmm, I suspect you'll get a lot of answers telling you not to go about it this way. And I must put in my two cents that I agree. While I don't agree with Carol Anne that you need to find someone you want to make love to, you're a 19 year old dude - you don't need to get online and make a business arrangement out of losing your virginity. Takes half the fun out of it anyway. You don't need to live in a sea of parties and hot chicks to lose your virginity in a fun, sexy, whimsical and perhaps even memorable fashion.

That said, if you are set on going the net route, don't use craigslist. Does your town/city have an alt weekly with personals? Might be worth checking those (Seattle/Portland, e.g., have 'lust lab,' which is basically like casual encounters on craigslist but less skeezy). It's probably worth paying for a subscription site like or if you wanna do it this way. There are experiential and aesthetic reasons for going the subscription site route over the free craigslist route - but there are also basic health and safety reasons.

And of course make absolutely certain to use protection.
posted by Lutoslawski at 2:05 PM on November 10, 2010 [1 favorite]

Don't. Make a profile on OkCupid and start going out on dates with girls. If you keep it up through the inevitable setbacks, things will work out physically with a girl sooner or later. (Of course, also keep trying to meet people offline - I don't care what college you go to, it's not as bad out there as you think it is).

If you think 19 is uncommonly old to lose your virginity, you've been watching too much tv.
posted by auto-correct at 2:06 PM on November 10, 2010 [39 favorites]

Mod note: folks if the only answer you have is "don't do this" do the OP a favor and say why or don't answer the question please. thank you
posted by jessamyn (staff) at 2:07 PM on November 10, 2010 [2 favorites]

Yeah man, you're really setting yourself up for a horrible first time experience. I know it's generally considered "girly" among men your age, but the first time really should hold some value to you. It's one of the few defining moments you get in life.

Also, chances are, you're going to be embarrassingly bad at it. You don't want a stranger who lives near you telling the tales of your premature ejaculation and crying. Just throwing that out there.....
posted by lattiboy at 2:08 PM on November 10, 2010

You remember when you finally sort of figured out how to ride a bike, but there are these scary little stops and starts and you keep losing your balance and maybe you even fall over and bust your ass a few times?

Now imagine doing that naked in the dark and while having to give a ride on the back of said bike to a complete stranger. Except they probably don't know you can't ride a bike and will probably get actively frustrated with your inability to do so smoothly. Does anyof that sound pleasant?

What should you know about random online hookups? They're not meant for virgins. It's not like hiring a hooker who you're paying to appear like they're having fun.

You want that hilariously awkward time to be with someone who knows the situation, likes you for exactly who you are -- and not despite who you are -- and will give you a hug and tell you to keep trying when you fall off that bike and bust both your asses.

What I'm saying is that it won't be fun and it won't be worth it and it might do some irreparable damage to your self-esteem.

Please don't hire a hooker, either.
posted by griphus at 2:09 PM on November 10, 2010 [11 favorites]

I'm sorry, your question as it is posted does not compute at all. "Most of the girls around here aren't that hot" and "I want to have sex with someone I meet on Craigslist casual encounters" are pretty mutually exclusive positions to take--I literally cannot imagine a college or university where the student body wasn't considerably more attractive, on average, than the population of folks posting on Craigslist casual encounters. (On average, I say, so anyone here who posts on CE, clearly you know I don't mean your adorable self.)

I don't think you're asking the real question here, and I would hazard a guess that your real question is "I don't know how to have relationships, but I want no-strings-attached sex, and that doesn't seem to be what my fellow college students are into." You may be right that it's not what they are into, so maybe Internet casual encounter sites are the right choice for you? If so, meet the person first in a public setting for coffee or whatever before making plans for your hookup, just to be sure you're not falling for the badger game or similar.

And the idea that you are somehow unusual for not having had sex at age 19 is kind of silly. At least 30% of 19-year-olds in the US have not had a sexual experience, according to the Guttmacher Institute. Have sex if you like, but don't do it just to "catch up" because sex is a fun thing that should be enjoyed for its own sake.

"I am a virgin due to having gone to a single sex school" is a statement that is so wrongheaded as to be ludicrous. You may not know how to relate with women as well as people who went to a co-ed school and as a result had more experience of friendship and school dances and dating and what-not. But the answer is not "find super-hot girls on Craigslist to end my pathological virginity" but "learn how to interact with women so that I can have relationships of all kind that bring me joy, from friends to fuck buddies to dates to long-term partners."

Let me suggest as a helpful resource to you. And good luck with everything.
posted by Sidhedevil at 2:14 PM on November 10, 2010 [53 favorites]

As a young heterosexual male, you're at a disadvantage when it comes to this sort of thing. You and several million other straight guys your age would like to have meaningless sex tonight, too.

First, optimize. Start with the OK Cupid blog,, which reveals a lot of trends and "yeah, that isn't particularly successful" or "this works out a bit better." Most of the information gleaned can apply elsewhere.

Then, volume. Take the approach a friend of mine does, which is that he hits practically every site ever. I have no idea how many sites he is on. They could well be into three digits. He is absolutely relentless about this. I do not know how he finds the time in the day, but he does. He is never without dates or some kind of sexual prospect because he is a dandelion, scattering his seeds upon the wind. Another very sexually driven acquaintance did something similar in meatspace: he took a lot of chances whenever the situation presented itself.

Unless you have some amazing qualities which can present themselves well in an online form, you may have some work ahead of you.
posted by adipocere at 2:16 PM on November 10, 2010 [1 favorite]

What griphus said, plus, WTF:
most of the girls around here aren't that hot anyway
It sounds like you need to get over yourself a bit, and learn how to interact with women as human beings. Are you "that hot"? Even in the most wildly successful scenarios, losing your virginity through online hookup is not going to bring you any closer to having an actual relationship with a human being. All the process and embarrassment and compromise that leads up to losing your virginity is a necessary part of learning how to be in a relationship. This may look like a shortcut but really it's completely irrelevant to what you're presumably looking for.

(Preview: looks like Sidhedevil covers a lot of this too)
posted by xueexueg at 2:23 PM on November 10, 2010 [6 favorites]

Hello, I am a 19-year-old straight male who is a freshman in college. I am a virgin due to having gone to a single sex school and the college I go to isn't exactly one of the top party schools in the nation and most of the girls around here aren't that hot anyway.

I'm a 40 year old male and this strikes me as damn odd. Single sex schools must have had mixers or something right? You didn't go to school year round, what do you do during the summers off? Did you actually try to hook up with any girls from college or are you just looking for a quick lay?

It's not clear from what you've written, but I'm getting the impression you're looking for an easy route to sex. That's understandable, but at some point you're going to have to practice talking to women and navigating the waters of flirtation and getting to know each other. Going for a quick hookup may short circuit all that work and leave you flailing about later in life because you never took the time to learn to enjoy getting to know someone.

Sex is nice. Sex with someone you at least know and like is better. Sex with someone you love is the best, especially if it's done multiple times over months and years. You're missing out on a lot by trying for a single night's hookup.

Finally, do you know how you'll react to sex?Have you ever had a relationship before? You may wind up falling for the person, yet they're only interested in sex, so you end up heartbroken and in emotional pain 'cause that simple physical act and the feelings and emotions it stirs up mean more to you than a one night stand.

So think long and hard about this route, because to me it doesn't sound like it'll fix much. If you do go this route USE PROTECTION, no ifs, ands or buts. Seriously.
posted by nomadicink at 2:23 PM on November 10, 2010 [2 favorites]

It is going to be much, MUCH easier to meet a woman your age at your school. Trust me. I'm ten years older than you, and one of the things I miss most about college was the built-in dating scene. There were always available people of your own age and interests to crush on, go out with, hook up with, etc. And there were tons of structured things to do that forced you to meet new people all the time. Not to mention that a lot of otherwise unattached people lived together in big shared houses, so you'd be meeting dozens more people at someone's house party, or by getting to know your roommate's friends, etc.

Now that I'm long out of school, I find it really difficult. Even with OKCupid and the like. It's really, really hard to factor in time to meet potential partners, one by one, after excruciating winnowing and weeding out online, in addition to my job, my pre-existing social circle (more and more of whom are married, engaged, or living with a long-term partner), household chores, other interests, etc.

I have also been in the position of hooking up over Craigslist because it's been such a long time since I met anyone I actually wanted to date. It sucks. Even for someone who is experienced and has lost a lot of preconceived notions about what sex is supposed to be. I feel bad about myself every time I do it.

Don't go down that road before you have to. Enjoy the college social scene while you have it.
posted by Sara C. at 2:23 PM on November 10, 2010 [5 favorites]

Lots of wowsers quoting from the Hallmark card company guide to sex. Here's a gay male (= not reared to think that sex is always a sacred gift of love) perspective. My first time wasn't with someone special. If I'd have waited for that, I would have been waiting till I was 25. It was with a random stranger and pretty awkward. And it was fucking awesome. In itself. Also fucking awesome not being a virgin any more. If I'd have been able to hookup online for my first time I would have but it was pre-Grindr, pre-Gaydar, pre-everything. So I met him on a bus.

Go for it. Be honest in your profile, perhaps imply you're kind of green. Use protection. Chances of success? You might carry it off, you might die in a fire -- regardless, your chances will probably be better the next time. Remember that more sexually active partners will have a higher risk of STIs, regardless of whether you use a rubber or not; not much you can do about that so be aware of the risk.

chances are, you're going to be embarrassingly bad at it. You don't want a stranger who lives near you telling the tales of your premature ejaculation and crying

Surely this is a fantastic reason to do it with a stranger rather than someone in your social circle.

it might do some irreparable damage to your self-esteem.

Oh gimme a break.
posted by dontjumplarry at 2:40 PM on November 10, 2010 [11 favorites]

Hi. I went to a school that consistently shows up on every Worst Party College list (we'd do a lot better if it weren't for Brigham Young and those damned military schools). Most of the girls there weren't that hot. Most of the guys there weren't that hot. But you know what? Everyone who wanted to get laid (i.e. took the first step in actually talking to the object of their attraction) got laid. A lot. And usually by someone they knew and liked. (Come to think of it, the vast majority of the people I knew who weren't getting any action were the guys who would constantly gripe about how un-hot all the nerd girls were and how they couldn't wait to go back home for Thanksgiving to hook up with all the high school girls. Asshole econ majors.)

You shouldn't give up without even trying. Chat up someone in one of your classes tomorrow and ask her out. Seriously. What's the worst that can happen?

And remember, the only one keeping score is you. The only one who cares if you're a virgin is you. (And maybe your grandma.) Don't let yourself get hung up on it.
posted by phunniemee at 2:42 PM on November 10, 2010 [6 favorites]

Y'know, I actually have a guess as to what school you're at - I heard the exact same sentiment expressed continually by the guys at my undergrad. I think others have covered how unattractive that attitude makes you, so on to the advice.

I think that you need to try being social at other schools. You're in the right age group, so it's not creepy to try to make friends and score an invite to another school's party. For example, one of my friends had great success expanding his social circle by taking social dance classes at a nearby college known to more than half female (and with a reputation for having plenty of hot women).
posted by Metasyntactic at 2:43 PM on November 10, 2010

I don't think your first time has to be with someone special, although there are advantages with that. If you'd rather it be with someone you don't know super-well, fine, whatever.

The reason I'd advise against doing this is that it may very well creep out your future girlfriends. (Or, alternately, be a thing you lie to your future girlfriends about.)
posted by Narrative Priorities at 2:46 PM on November 10, 2010 [3 favorites]

When I was your age (never thought I'd say that phrase) I did what you are considering. I was way too tightly wound to hook up the normal way. Luckily, im gay and casual sex is possibly what we do best aside from throwing theme parties and quoting the golden girls. So I hopped on an AOL chat room and set up "a date" - this was still in the day of a/s/l, and I was so clueless about the whole thing I didn't even really understand some of the finer points.

For example: don't be blunt about it. "I'm really interested in losing my virginity" is a curiosity, not a turn on. "Hey baby, you're good looking what are you doing tonight? Oh, me? Well, if you were free I was hoping we could get together, you know - something low key, maybe watch a movie or something." Then, sure you turn a movie on. And you put your arm around her. And then you make out. And then... well that's apparenty where things get low key.

Anyway, I was (am?) too much of a woody Allen character to have done things the "right" way with okcupid and dates and whatever. And I'm not ashamed of what I did. And you shouldn't be either.

Be calm, be respectful, be a good listener and a good communicator, be prepared, and most of all: have fun.

As for which resource to use - facebook might not be a bad bet. It isn't as tainted as, say, craigslist in terms of "meatmarket-ness." I think AOL chatrooms are probably a bit over at this point.
posted by jph at 2:47 PM on November 10, 2010 [1 favorite]

Please tell me everything you know and think I should know.

No offense but your question makes you seem to be a bit naive about sex. Many students at your school are most likely sexually active even if it is not a party school, and the comment about the lack of hot women just sounds like sour grapes (plus as Sidhedevil said the idea that people on a casual hookup site would be more attractive on average than any group of random college-aged people is dubious).

I disagree with some others that have said having your first time in a casual situation will necessarily be terrible or that virginity is always worth saving for the right person, because in the grand scheme of things even an awkward and regrettable first time is probably not a big deal. I do think you possibly aren't coming into this with the right attitude though and you may want to think about what you actually want out of sex and what kinds of relationships you want to have in your life. Also, two major things that you do definitely want to worry about when it comes to sex are pregnancy and STDs. A condom is only going to protect you so far in both of those areas so keep that in mind.
posted by burnmp3s at 2:49 PM on November 10, 2010

If you're set on losing your virginity this way, I would actually recommend you go to someone who does sex work professionally. That way, at least there will be no expectations from you other than "have you got x dollars?" Plus, they may have more experience dealing with people like you.

Also, if you're angry about being put in the classification of "people like you," refer to above where you unilaterally discount all the women at your school, and then realize that's how it feels.
posted by Jon_Evil at 2:51 PM on November 10, 2010 [17 favorites]

Be honest about your experience level in your profile. But - most importantly - find a way to do that and still be careful.

You don't know who you are meeting when you set up a meeting like that. I would use a Google Voice number and an email address you set up especially for this communication, and I'd probably look a little bit away from where I actually lived. I would meet that person in a public place first, again a ways away from your regular routine, and I'd see what kind of feeling I got from them - if it is okay, I'd proceed to a hotel that I had picked out, and I wouldn't go back to someone else's place or their choice of hotel if you can help it. And use protection for the actual sex.

Yes, that sounds uber cautious, maybe I have seen too many SVU episodes or read too many news stories, but you want to be smart about your own safety especially if you are intending to put yourself in a vulnerable position (naked and having sex).
posted by mrs. taters at 2:51 PM on November 10, 2010

perhaps imply you're kind of green

Oh god, if you go this route, you absolutely need to say upfront that you are a virgin.

For one thing, if your partner is more experienced than you (which they most likely will be if they are cruising online for hookups, and you're a heterosexual guy), she will know. And think less of you for not just saying so from the beginning. Or if for some reason she doesn't figure it out, she'll just think you're a bad lay. Maybe none of this matters to you because you don't care at all about your potential sexual partner's feelings or enjoyment. If that's the case, you need to seriously question your own motives, because that's a shitty way to behave to another person.
posted by Sara C. at 2:58 PM on November 10, 2010 [5 favorites]

Maybe none of this matters to you because you don't care at all about your potential sexual partner's feelings or enjoyment. If that's the case, you need to seriously question your own motives, because that's a shitty way to behave to another person.

Except to a professional sex worker, who expects only to be paid promptly and in full, to be treated with basic civility, and to have their boundaries respected. OP, if what you want is to get your rocks off and you don't care about the other person's enjoyment, maybe a professional is the best bet. Just be polite to them, as you are (or should be) to the person who cuts your hair or cleans your teeth.
posted by Sidhedevil at 3:10 PM on November 10, 2010 [1 favorite]

maybe a professional is the best bet


Also, if you want to verse yourself is normal, adult sex "culture" a bit, check out Dan Savage's podcast series. (iTunes link.) Yes, some of the questions are out there, but most of it is very vanilla, very regular. Normal people asking normal questions. (Some more normal than others.) And I'm sure I've heard your scenario there before. It's not uncommon.

In that case, I feel like Dan said to hire a pro and treat her well.
posted by supercres at 3:21 PM on November 10, 2010

The first time you have sex is generally not the best thing ever, but it's made much more pleasant by being with someone who at least cares about you a little.

My first advice to you would be to relax; sex will happen sooner or later. In my experience, the more you worry about it, the less likely it is to happen. Just chill out and do whatever it is you do, and sooner or later someone will pop up who wants to have sex with you, even if you've spent no effort at all to find them. It's one of those weird natural laws.

But, if you feel that you must have sex right now, with someone, it's really a pretty easy thing to do. Craigslist is an easy option, but be aware that finding a sexual partner that way is akin to screening potential roommates; you're going to get a shit-ton more weirdos answering your ad than people you'd actually like to bed down with. There are other services, of course - OKCupid, Yahoo personals, &c. - but they're as likely as not to yield similar results.

If you're in a college town, you can probably find a house party to go to on any given weekend. Those places are good for finding frisky 19 y/o girls who want to fool around, particularly if there's drinking going on. You're probably in a class or two with girls who'd like to get down, too; is getting into a study group an option? Athletic activities of any kind are often a solid bet for meeting people, too, with the added benefits that they are good for you, and tend to foster a sort of 'esprit de corps' (For me it was capoeira. Singing + physical grace and exertion + tight outfits = hot).

Lastly, I find it hard to believe that on a college campus pretty much anywhere "most of the girls around [there] aren't that hot anyway," and that that is such an impediment to you that you'd rather just have sex with a stranger you met online. If only a 'hot' girl is going to flip your switch, maybe you've set your sights too high. That kind of 'waiting for the perfect person' attitude will probably keep you from having sex with anyone, forever, and is kind of lame besides.

Anyway, good luck. And be safe about it, no matter what you do.
posted by Pecinpah at 3:27 PM on November 10, 2010 [1 favorite]

Dude, are you for real? I can understand where you're coming from- sometimes, sex can start to seem like such a Big Deal that you just want to get it over with and leave the Virgin Club behind forever. The thing is, sex isn't some kind of magical act that transforms you into the kind of person who has sex all the time. It's just another kind of intimacy you have with another person, another thing to do with someone you think is hot when you get naked together.

What exactly are you trying to get out of this? What do you want your life to look like on the other side? My guess is that if you make this happen, you'll still be in basically the same situation you're in right now- kind of lonely, frustrated with the social scene at your school, and not having sex. You may have marked "Had sex, one time" off your life to-do list, but that's just the beginning!

You need to remember that you're playing the long game, here. People expect a certain level of idiocy from freshmen boys when it comes to sex and relationships, but that shit gets less cute when you're older and the girls you're going after know a little better. Learning how to do all of this relationship/sex stuff the hard way is exactly what college is for! I'm worried that if you start down this path, divorcing the act of sex from the process of developing a relationship with someone that leads to sex, you'll be back on AskMe in 5 years wondering why all of your friends have hot awesome girlfriends and you can't get a date.

There are a million questions on this site from guys asking how to flirt with girls, how to get girls to go out with them, how to sustain a relationship- go read them.
posted by MadamM at 3:48 PM on November 10, 2010 [5 favorites]

I agree with everything dontjumplarry said; the one caveat I might add is that if part of your reason for doing this is so that down the line with someone whose opinion matters to you, you will be good or at least better in bed - I actually think guys whose sexual experience mainly comes from one night stands are generally a lot worse. Being good in bed is all about learning what this individual person likes, and I think that can take a lot of time and trust to learn, especially if you're dealing with people (and especially with young women) who might be shy or bashful about it. And I think guys whose experience comes from one night stands have mainly just learned what *they* enjoy and develop/become attached to this one-size-fits-all set of moves that not everyone enjoys (and that, in some cases, *nobody* they have slept with has actually enjoyed). Apologies if sexual prowess is not in fact a factor for you in this.
posted by Ashley801 at 3:50 PM on November 10, 2010 [2 favorites]

I also think I should say that regardless of my or anyone else's feelings about sex work, launching your sexual life with an experience where the the other person's enjoyment doesn't matter *at all*, or a experience where they may feel obligated to act like they like what you're doing even if they don't, is really not the best thing for your development into a good sexual partner.
posted by Ashley801 at 3:58 PM on November 10, 2010 [4 favorites]

Go for it any way you like, craigslist, sex worker, what-have-you, use protection. Saying your subsequent sex life will be irreparably damaged by the wrong choice now, or hired help is 'really not the best thing for your development into a good sexual partner' just ain't right imho. You clearly want to get the virginity thing out the way, it's getting you down, so go ahead. Of course real relationships are much more fun and much more difficult, but you'll find that out in due course.
posted by londongeezer at 4:22 PM on November 10, 2010

As you can see, lots of people are injecting a 'don't do this' from a moral sense into here. I don't necessarily agree with them, but it really depends on your motivation. Why do you want to lose your virginity badly enough to stage a random hookup?

Is it performance anxiety? Peer pressure? Feeling like you're too old to be a virgin? In these cases I would be wary of rejecting everybody's advice. It would suck to do it and then regret it because you realized you were making this decision for people other than yourself. So I suggest you really think about this.

However, I'm going to assume based on your post that your reasons are coming from you, internally, that you don't care about 'making it special' and you just want to get laid.

Firstly, if you are looking for a craigslist hookup, you should probably lower your attractiveness standards. Getting hot women to sleep with you probably isn't going to happen over the internet without some substantial effort involved on your part. If that isn't what you want, I would suggest hiring a professional.

If you are interested in something intermediate between a hookup and a traditional date, I might third the suggestion of trying OKcupid. You'll get to look at a fair number of women, but the stakes are pretty low in terms of talking to people and rejection. If you have a good connection with somebody, you might want to sleep with them even more which is a nice bonus.

In terms of what to say, I would definitely tell them that you are a virgin. You can put this in your profile or wait until you're talking to somebody, up to you, but do make sure to communicate it. That will take a lot of the pressure off you to perform, and you won't have to be second-guessing yourself ("Does she know?") the entire time. Hopefully this will let you enjoy it more.

Also, I think you'll be more successful if you can show an honest desire to make a good sexual partner. Good partners, for example, care about the sexual pleasure of both parties and not only themselves. If you have a fantasy that involves pleasing a partner, mention it (wanting to go down on a girl, get her off multiple times, whatever). If you make it all about you, nobody is going to care because they don't know you.
posted by zug at 4:36 PM on November 10, 2010

If this is your first time, you're nervous and desperate about it, and decide to go toward the "random encounter" angle of things, you could be setting yourself up for some pretty horrible sex. (And by "Horrible Sex," I mean "No Sex." Nobody's first time is particularly glamorous, but you want to be able to at least get it up, and enjoy the damn thing.)

You should at least try to establish something that vaguely resembles a shadow of a traditional relationship, even if you put the entire thing together over the course of a single evening ("a movie or something low-key," like jph mentions).

"Sex with no strings attached" isn't much of a turn-on when stated as bluntly as such. Foreplay matters, and you should at least pretend to know and like the person that you're fucking. (If you're going this route, it's very, very important that the girl understands that you're being shallow, and that the sex is not some sort of DTR. Also; rape is bad; know your boundaries; no means NO.). This route also enables the possibility of a real relationship to form around the sex, should the two of you end up enjoying sleeping with each other.

Work on figuring out how to make women want to sleep with you, even if it's only for a casual hookup (it's not terribly difficult!), and buy some magazines and a fleshlight for the interim. Moral issues aside, I think that you're setting yourself up for some really bad and unfulfilling sex that might not even happen.

Disclaimer: I'm a homo, so this advice might not be valid for your instance. I'll also use this small text to vent about the fact that almost everything has become some sort of innuendo for sex. Sometimes I really just want to watch a damn movie!
posted by schmod at 5:15 PM on November 10, 2010 [1 favorite]

Here are the three things that I think you should know, as per your question:

Numero uno: the reason you're not a virgin isn't (just) because you go to a single-sex school; it is also because you're apparently limiting your social life to on-campus activities. You have to go out, to parties and events and extracurricular things, meet people and risk rejection asking girls out.

Two: If you're already doing this and it isn't helping, it might be because the attitude you express here anonymously ("...and most of the girls around here aren't that hot anyway") is coming out in your interpersonal interactions. Odds are that you, at age 19, aren't "that hot" either. Perhaps your expectations are based on media portrayals and objectification, rather than acknowledging women as human beings just like you. Try taking a step back and try to get to know some women as friends, and perhaps one or two as girlfriends, without worrying about the getting laid part.

Three: Dude, you're 19. What's the rush?

Now, about the online sites in particular: places like OKCupid are free, and fine, and rejection is easier to deal with. Here are the risks:

1. Someone you know (who's on the site looking over someone's shoulder, or for a laugh) will recognize you and humiliate you by sharing the knowledge. So if you do this, remember you're posting your personal information (and relationship-seeking status) for the world to see. There's no backsies on that.

2. You will be interacting with women who can -- and will -- reject you without a moment's thought. Want to know what it's like to be objectified? Be a profile on a dating site. In the habit of objectifying people already? A dating site will feel nice and comfy to you. This will not get you used to rejection in the real world, which is a necessity if you want to succeed in the real world.

3. If you get out there, take a few risks, ask a few girls out, you might not get laid -- but you might make some girl friends who will end up helping you learn more about yourself, improve the way you dress, get rid of some bad habits, get a better haircut, and so on. Nothing helps you be (superficially) attractive to women like having women tell you how badly you suck, and how to fix those things. Online dating is not going to help you get this kind of feedback, unless you meet people often (and without the goal of just getting laid and moving on, so you'll never be close enough for them to help you with your faults.

4. Online dating is a legitimate source of relationship starters for a lot of people,'re 19. You're just learning how to be an adult. You can't even drink yet. You are not going to meet women who are more "hot" than your local girls online, because you're competing with all the other guys who can jump on to OKCupid et al, and why would they be impressed with your 19-year-old ass unless you have something in common with them? Something beyond OKCupid, I mean. And that means you need depth and complexity*.

In short: don't do it, at best you'll postpone your jumping feet-first into the person-to-person dating pool and regret it later, and at worst you'll end up humiliated. Instead, go take some classes, get a job, get some hobbies, go to parties, take long hikes through the woods, read, experiment, and become a person with a healthy perspective* and a depth, complexity and confidence that are attractive.

*people who say things like "...and most of the girls around here aren't that hot anyway" do not have this.
posted by davejay at 5:23 PM on November 10, 2010 [5 favorites]

Here's something to keep in mind:

If you're trying to lose your virginity so that you can tell other people you're not a virgin – and this, frankly, is the main reason I can think of that a college student would be jonesin' to do the deed in this manner – you're going to have to tell them this story, too.

Or lie about it.

But then you might as well lie about the whole thing: "Sure, I had great sex all the time with my sexy high school girlfriend and boy was it great and sexy."

The other reason you might want to do this, and stop me if I'm wrong, could be that you want to cash in your V-card now so that when you get around to sleeping with someone who you actually like, you won't seem like a virgin. Here's a hint: she can't tell. (I mean, she will probably know you're not a regular casanova, but whether it's your first or your tenth time is not going to be apparent.) Also – as others have said, 19 is NOT old. Lots of girls in your class year are certainly also virgins. And of the men and women who are not virgins, the vast majority of them are still pretty inexperienced and will be awkwardly fumbling they way through things.

(These are things, by the way, I wish someone had told me when I was 19.)

As others have also said, this one-off chance encounter will not be very satisfying, and quite possibly embarrassing, and you won't learn anything from it. I'm not saying don't do it because it's morally wrong, or that it's going to be damaging to your emotional development, or any such reason. Do it if you really want. I'm just saying, I don't think it's going to accomplish what you think it's going to accomplish.
posted by dixiecupdrinking at 5:28 PM on November 10, 2010 [3 favorites]

Be completely open about what it is that you want and where you are, experience-wise. There will be women who are turned on by the notion of taking someone's virginity, and if you're straightforward about your lack of experience, then theoretically your partner will be ready to adjust to that right away.

Don't jump at the first offer of sex. Go on a date or two first, check the person out, stay in public the first few times you meet her. Make sure a friend knows where you are and how long you plan to be out. Arrange to stay in contact with that friend sporadically throughout the night. Hopefully all of those precautions will be unnecessary and therefore will feel very silly to have done. You'd rather feel silly than get in trouble.

If, during that process, you decide this potential partner isn't right for some reason, trust your gut. There will be other opportunities and other partners, and your instinct is your best friend. Err on the side of personal and emotional caution.

Once you do meet someone with whom you'd like to continue, talk to her about what she wants as well as what you want. You'll find the experience enhanced if both of you are pleasing each other. Be open and receptive, listen as well as talk. Don't let your preconceived notions of what sex is supposed to be prevent you from exploring your sexuality or hers. It's ok if you try something and it doesn't work for you; it's less fun to want to try something but be afraid to.

Be safe. Have fun.
posted by Errant at 5:30 PM on November 10, 2010

What do I think you should know about doing this? That future girlfriends will think it's creepy. I dated a guy who lost his virginity this way. I was brainwashed in Catholic school so I might be preachy about this but I think that when you get with someone, you're getting busy with them and all of their previous partners. So I'm dating this guy and things are going well and I had to make the choice whether to get busy with him and random internet person. Do you want to put your future partners in that position?

Again, I might be too preachy but I felt like he didn't respect himself or me. He didn't care about himself enough to wait to lose his virginity to someone he cared about and I could be replaced on Craigslist.

Also, for what it's worth, before I saw lost-my-virginity-to-a-stranger guy, I dated a 25 year old virgin. While I thought 25 year old virgin took sex way too seriously, I'll admit that I had a little more respect for him because he had respect for himself.

Finally, the #1 property you are looking for in a first-time sex partner is hotness? Seriously? Are you Jonah Hill?
posted by kat518 at 6:22 PM on November 10, 2010 [1 favorite]

I guess I'm not as romantic as some of the other responders, I don't have any concerns about people seeking casual sex for your first time. I'm a woman who lost her virginity freshman year of college quite purposefully with someone who was not boyfriend material.

That said, I think you'll have a whole lot more luck if you back away from some of these stereotypes. At best, they make you sound really naive. At worst, they could make you sound like a bit of a pig.

"Not exactly one of the top party schools" has what on earth to do with you finding a sex partner? Do you think that you'll only find casual sex with women who are drunk? Do you think that the women at "party schools" are just easy? See, this doesn't make you look good.

I have no doubt that there are plenty of attractive women at your school, but I don't even know why "hotness" is relevant. C'mon, are you looking for casual sex or prom date? I actually suspect that you said this because you're too nervous to try with anyone at your school. But rejecting all the women en masse as not being up to your high standards makes you sound like a jerk who takes out his insecurities on other people.

That said, you very well may find someone by advertising for a casual encounter. If you just want to "get it over with," it's not the worst idea ever. Whether it will satisfy whatever you expect from "losing your virginity" is not exactly a guarantee, though.

Look, penis-in-vagina sex is a whole different sensation and you've got a lot invested in the experience and you're likely to come involuntarily, very fast, and awkwardly. If your hookup isn't aware of your inexperience, it would not be unusual for her to be disappointed, annoyed, or nice-but-pitying. If you do disclose your inexperience, you're going to attract some respondents who are more into power-games than sex, and may even assume you're role-playing. This may not be the sort of sexual dynamic that you're after. That fantasy ideal of a hot stranger who will patiently initiate you into the marvelous world of fucking with no strings isn't impossible, but... might be easier to just meet a nice girl on campus with whom you have some sexual chemistry. Or a professional, as mentioned upthread.
posted by desuetude at 6:30 PM on November 10, 2010 [8 favorites]

The set of "women who attend Unfun University" may overlap with the set of "women looking for a Craigslist hookup" in ways you are not currently anticipating.
posted by fairytale of los angeles at 6:43 PM on November 10, 2010 [7 favorites]

Go on dates, try to meet people you like, people who like you, people who you'd like to know better (even if you only want to jump in the sack with them). Be an interesting person. Go out and do things.

Do you think there isn't anyone around who will want to date you? Or that they don't want to go out with you, because you are The Virgin? That your life will change in a huge way because you've had sex? Maybe you should reconsider your feelings about this. Otherwise you might go through with it all and just be right back where you started.

My 2 cents, is that getting to know someone you like, awkwardly undressing each other, fumbling around in a dark room trying to kiss each other is by far a much more rewarding experience. Having sex for the sake of not being a virgin anymore just makes it about the act, which is not nearly as much fun or as exciting.
posted by everyday_naturalist at 7:35 PM on November 10, 2010

Well look into PUA-Stuff
posted by yoyo_nyc at 8:46 PM on November 10, 2010

Foisting your virgin self on an unsuspecting woman is pretty inconsiderate. It's guaranteed that you're going to be completely terrible. Speaking as someone who for a while had the nickname "Virgin Killer", it's been my experience that most virgin men can't even tell if they're in or not. They start thrusting away, and you have to say "Excuse me, I hate to interrupt, but you would probably enjoy this a lot more if you were actually, you know, IN." There's pretty much nothing in it for the woman unless she's got an emotional investment in you. So yeah, either pay for a sex worker, or adjust your expectations and wait until you find someone you can have an actual relationship with.
posted by MexicanYenta at 8:54 PM on November 10, 2010 [3 favorites]

You should at least try to establish something that vaguely resembles a shadow of a traditional relationship, even if you put the entire thing together over the course of a single evening ("a movie or something low-key," like jph mentions).

I don't know. I sure wasn't looking for "traditional relationship" the first few times I got laid; if I had, I probably would have stayed a virgin even longer than I did. There's nothing wrong (in my world, at least) with getting laid your first time (or first few times) any which way you can -- it can be really tough to get over the hump (so to speak), and I think most people understand that people are sometimes willing to do some pretty extreme things to do so.

That said, this:

I am a virgin due to having gone to a single sex school and the college I go to isn't exactly one of the top party schools in the nation and most of the girls around here aren't that hot anyway.

says to me that your issues are deeper than just being a virgin, and just getting laid isn't going to solve them. You'll be happier if you figure out how to connect with people and find happiness where you are than you will be if you have a thousand random hookups. But still, like I said above, sometimes you just have to find a way to end the dry spell, and you can figure out how to find long term happiness somewhere down the road.

Also, this statement: most of the girls around here aren't that hot anyway? Wait until you are older, have nose hair, are balding, and all the college girls call you "Grandpa." Then you will laugh and laugh at your current pickiness. You will never, ever, in your entire life, be surrounded by this many beautiful, smart, and available young women (and men, if you decided you swing that way, too). Seriously, never again. Take advantage now -- make friends, go out, get laid -- because twenty years from now those young cuties won't even ask you for directions, never mind give you naked backrubs in their dormrooms.
posted by Forktine at 9:42 PM on November 10, 2010 [2 favorites]

When I was a college freshman, I had a friend who was convinced to sleep with a girl he was dating but didn't want to get serious with because she told him he was the only guy in college who was a virgin. Guess what, he came to college, and he was actually the only one of his friends who wasn't a virgin. Being a 19-year-old virgin is not remotely weird. A lot of guys who brag about their sexual experiences at that age are lying. A lot (probably most) 19-year-old girls don't care if the guy they date/sleep with is a virgin, and I bet a lot of them are virgins themselves.
Saying the girls at your school aren't hot enough is a non-starter. You will get nowhere with this kind of attitude.
If you're having a hard time meeting people IRL, try OKCupid. It's best for young people. There might be girls on there your age who are looking for hookups, but I bet not many, honestly.
posted by elpea at 11:40 PM on November 10, 2010 [2 favorites]

A lot of guys who brag about their sexual experiences at that age are lying.

At any age. *sigh* I speak from experience.
posted by desuetude at 12:03 AM on November 11, 2010 [1 favorite]

Trust me when I say that 19 year old virgins at BYU can and do have sex, when they act like the kind of people other folks who are looking to have sex want to have sex with. Sure, their roommates might turn them in for violating the honor code afterward, but that's not the point.

I think you have a lot of other things to do (before getting to the Craigslist stage) to turn yourself into the sort of person other people want to have sex with.

But no matter what, do not use the phrase "the girls here aren't that hot" in any ad or online profile. Because, dude.
posted by SMPA at 5:50 AM on November 11, 2010

You will never, ever, in your entire life, be surrounded by this many beautiful, smart, and available young women

You're just gonna panic the kid. And that's not necessarily true anyway. One big problem with being 19, OP, is that many women your age are going to be attracted to (even slightly, sometimes a lot) older, more confident men. This will go on for a few more years, until you become one of those men, which is something you can actually work on doing.

Do it right, and you'll be "surrounded by beautiful women" (whether as partners or admirers or friends) for the rest of your life, or at least until you need diapers and a walker. It doesn't get harder, it gets *easier* as you get older, at least as long as you don't let yourself go physically. You think George Clooney wishes he was 19 again?

You think you get there by getting laid once? Nope. You get there by developing your charisma, your earning power, your physical strength, your look, your affect, your accomplishments, your circle of friends. Go to the gym, do your homework, make some money, dress sharp, play in a band, cultivate a funny persona, learn to hold your liquor, help friends move, be gentleman to women of all ages and statuses, whatever. *Women find male confidence, charisma, and ability "hot."* Simple as that. It matters so much more than your abs or your haircut. It trumps how you look by a mile. It's basic evolutionary programming.

Until then, your comment about a lack of "hot" women, while absurd in empirical terms, pretty much has an equally stereotypical complement on the female side. Your "unhot" female classmates (I'm with everyone above who says you really need a reality check there; hot is not a look, it's a way of self-presenting as an erotic being, and you just don't inspire it in women, it's not their fault you don't find them hot) look at you as just another skinny-assed, desperate college boy. That's boy, not man. And they say things like "the boys around here are all so immature," and they're thinking of boys like you. *You* aren't "hot" either.

Fix that.
posted by fourcheesemac at 6:15 AM on November 11, 2010 [6 favorites]

Not only are you pretty naive about women at this age, but young women are also pretty naive about men. It gets way easier to meet people for relationships when everyone is a bit older. Most people don't really bloom till they're well into college or after graduating.

When I was nineteen, I traveled abroad to a country where sex work is legal. I was a virgin (never been kissed) and seriously considered losing it to a sex worker, but I didn't do it because of all the uncertainty:

* Will the sex be any good?
* How will purchasing sex affect future relationships?
* How will purchasing sex affect your mindset about sex in the future?
* If you're in a country where it's illegal, will it be safe?

You can't really know the answer to those questions until you've had significant sexual encounters of your own. It's a catch-22 :(
posted by grammar corrections at 6:46 AM on November 11, 2010

Not bothering to preview all these responses but would like to add that if you are insecure about being 19 and a virgin just don't. Spend your mental energy on something more important like developing yourself as a person who other people will find fun and interesting and want to sleep with on the merits.

My amazing boyfriend is certifiably gorgeous and wonderful -- was a virgin at 28 when we met. He's not a religious-nutter, he's just shy. I am not shy, I am shameless and I was definitely not a virgin when we met. I really could have cared less.

He's a great guy and whether or not he'd done tab A into slot B was the least of my concerns. Anyway, the teaching part has been fun.
posted by blue_bicycle at 7:04 AM on November 11, 2010 [3 favorites]

most of the girls around here aren't that hot anyway
I don't think your issue is not having had sex. I think the issue is that you haven't learned how to be around women. I went to a university that had ex-single-sex pupils there. Some were perfectly ordinary people; some were very screwed up socially and romantically. One of them lost his virginity to a sex worker, for the reasons you give here, and another didn't until he was twenty-nine. Both of them are happy people now.

And we don't really have 'party schools' where I am - we just get together with friends, get pissed, and pair off, and do so mostly happily. Understandably if you are in the US drinking is out, but go out, socialise. Remember women sometimes want sex with no strings too. Don't lead on girls who want something more - be upfront. Use protection. Remember you're with a human, not just getting your rocks off. Don't do it for the sake of it. It's not going to be true-love, but at least make sure you fancy them, otherwise it'll be about as sexy as rubbing against someone's elbow for three minutes.

Remember it's probably not going to be mindblowing or a life-changing experience, as you want to dispense with it and get it out of the way like a root canal, so you might just feel a bit of relief afterward and little more, and it probably won't be that much more like the movies than the dentist scene in Little Shop of Horrors.

Oh, and do not do PUA stuff. It will turn you into a creepy asshole and girls WILL see through it. Treat women as a whole, not a hole.
posted by mippy at 7:49 AM on November 11, 2010 [5 favorites]

Hey. 20-year-old virgin here. You're wasting your time worrying about this shit.

I've got a pretty diverse group of friends. Sexually speaking they range from "haven't really ever dated anybody" to "got laid younger than I had my first kiss". Honestly, the only ones whose sexual statuses really affect their characters are the ones I think talk way too much about the girls they've hooked up with. Usually Theater majors, who as far as I can tell only exist in college to fuck every other Theater major and then tell all the other Theater majors inappropriate details about how the hook-ups went. Not that I'm against their lifestyle but it sure gets boring to hear about.

There will be virgins at any age and there will be people too impatient for virgins and there will be people who take a lot of pride in getting a virgin up-to-speed. It's not like you've got a door closing or any such. People have sex even when they're not in college, I hear.

One thing that almost goes without saying is that you're only going to enjoy your sexual encounters inasmuch as you enjoy your sexual partners. In the long term, knowing what you're doing matters way less than how much you like doing it. (This is true for things that aren't sex, too.) In the short term — who cares? If you're worried about friends looking down on you, either get new friends or lie to them. If you're worried about your own self esteem, know that the actual act of fucking isn't going to make you feel any better about yourself. It's not going to make you any better at fucking people you're not in the mood to fuck anyway. The nice flip side to being a miserable young adult with uncontrollable hormones — and remember, I'm more-or-less in the same place that you are — is that when you meet a compatible hormone sack your body pretty much knows what's supposed to go where.

Relax. Be cool. Try getting to know people at your college without writing them off as somehow unworthy of you. You'll find that once you start actually discovering who somebody is, they magically become fascinating and beautiful. You're in college. Stop buying into the crap about "beautiful people" and "undesirables" or whatever terms your particular watering hole uses. It's hard to find somebody our age who isn't just about bursting with vitality and energy and enthusiasm.

And above all try not to think of college as a mere fuckpit. Here is an exciting place with opportunities in a zillion places at once. Sex can be one of them; it doesn't have to be. There's nothing wrong with that.
posted by Rory Marinich at 11:59 AM on November 11, 2010 [6 favorites]

Listen to Rory. I wish I'd known more people like him when I was your age.
posted by mippy at 4:01 AM on November 12, 2010

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