Please Advise: My friend wants me to take her virginity.

Nerve readers help out a guy who just wants to be a good friend.

Each week, the inbox of our venerable advice columnist, Miss Information, is flooded with queries. And although she makes a valiant effort, she cannot answer them all. To deal with the surplus, we've decided to turn to you. So, don your spectacles and help this gentleman out. You can give him advice in the comments below, or, if you'd like to share what you wrote with your friends, on our Facebook page.

Dear Nerve,

One of my oldest friends recently asked me to take her virginity. She's twenty-six, and for a variety of reasons of varying sensitivity, the deed has just never been done. She's starting to feel (in her own words) "a little desperate, a little left out, and a little lost." Though the idea was broached over drinks, she's asked me about it repeatedly since she maintains that she doesn't have any feelings for me, and that this would strictly be (again in her words) "an educational experience." 

I have mixed feelings about this: I don't really have a problem with the idea, but the more I think about it, the more I can't help but think that this is something we'll both regret later. It'll forever color our relationship, and something about it just smacks of high school to me. She's repeatedly reassured me that she thinks this is best, and admittedly, it's better that I "help her out" than some random guy. I just want what's best for her I don't want to be a source of regret for her, or always leave her wondering "what if?"

— A Good Friend

Commentarium (82 Comments)

Feb 24 12 - 1:44am

Yeah, it will forever color your relationship regardless of what she claims. Help her out and find someone who isn't as random. Tell her your friendship with her is too important to possibly risk any change or tell her it'll affect you even if it doesn't affect her.

Feb 29 12 - 7:12pm

Fuckit, I'd ride that shit like a rented scooter. A girl as a "friend". Yeah right.

Feb 24 12 - 1:53am

I wouldn't touch that with a ten-foot pole.

Unless you're ready for the potential fallout, and think it worth the risk, I'd give this a miss. You never quite know how a post-virgin will react, despite what she may think now.

Feb 25 12 - 12:03pm

I agree. If you think at least one of them will regret it and the idea seems unappealing in any way, then LW1 should *ahem* withdraw himself from consideration. LW1's feelings count too. I think LW1's being realistic, and frankly, I deem him a true gentleman and good friend for considering the emotional risks. (And if he's not physically attracted to her, well, then she should respect that, too. Call it Lesson Number One. Friends don't have to fuck friends, not even if they ask nicely.)

I'm sure the friend imagines that losing her virginity to an old friend will somehow provide sexual training wheels that will let her figure out the mechanics without as much emotional risk or exposure, except of the positive kind. And, as an added bonus, being old friends will somehow provide some sort of guaranteed "special-ness" that most inexperienced people privately think intimate acts require.

Yeah, it doesn't work that way. If you want to get freaky with people without risking anything, go on Chatroulette. But if you do, then you have to eventually take the same physical and emotional risks that everyone else has to take. LW1 would be doing his friend a much better favor by being her wingman and finding a third party to do the deed.

Feb 24 12 - 2:22am

It sounds like you have misgivings about this, and for good reason. She wants to use you as "an educational experience" because she's feeling lost and desperate? How terribly sexy. You're right, it isn't high school; tell her to be a grownup and find a partner who's attracted to her and thrilled to introduce her to the magical world of sexy time. Hook a sister up if necessary. But a half-assed convenience fuck with a friend who's only there out of pity is hardly a suitable introduction. You're not doing her any favors with this favor.

Feb 24 12 - 3:07am

If you're any good at all, expect her to want to be more than friends after hooking up. Sure it may change your friendship, but if you are attracted to her, how could you say no? You're playing with fire here, and you could lose the friendship either way, so at least get laid!

Feb 24 12 - 3:47am

When I was younger, I went through a similar situation, except I was the virginal girl. I was younger than your friend is, but just as desperate. A friend made a move on me, and I practically begged him to have sex with me. In the end, he was game, but I was humiliated. We didn't have sex, I backed out at the last minute. I realized I was about to lose my virginity to a guy I didn't care about and who didn't care about me. We haven't spoken since. I guess my point is, your relationship will change either way at this point. There's really only two options: Reject her (which may or may not damage your relationship), or fuck her (and magically stay friends, become a couple, or ruin your friendship. ) It's not fair of her, but she's put you in a spot where you have to decide.

Feb 24 12 - 8:38am
Instructive Quote

Step 1: Rent 'Grumpy Old Men'
Step 2: Follow this advice from Grandpa Gustafson, 90, to his son Max, played by Walter Matthau:

"You think I should call her?"
"The woman."
"Well, let me tell you something, John. The first 90 years, or so...go by pretty fast."
"The first 90 years go by fast."
"How would you know?"
"You're just a damn kid."
"I didn't say it, you did."
"Well, they do. They do go fast. Then one day you wake up. And you realize...that you're not 81 anymore. You begin to count the minutes rather than the days...and you realize that pretty soon you'll be gone. And that all you have, see, is the experiences. That's all there is. Everything! The experiences! You mount the woman, son. Or else...send her out to me!"

Feb 24 12 - 11:57am

You have just won my internets hero heart shaped badge

Feb 24 12 - 9:28am
Bruce Lee

Do it. She has already colored the relationship, by mentioning it, and you have exacerbated that by not shooting her down the first time. So be a man or whatever and do it. Then get some space. Take some time off. She will need to figure out that she just gave her v card to a dude she didn't love, which may or may not bother her, but you def don't want to be around for that. Just do it and make space.

Feb 25 12 - 11:44pm

I agree. Do it and.... expect that she may back out at the last min.... emphasize how this is just educational - maybe give her a few tips while youre at it to drive that point home. don't expect her to orgasm - she may be too nervous....

Feb 27 12 - 2:53am

Do it and make space? That's the absolute worst thing that you could do. A woman will almost certainly not take it well when a man with whom she has any sort of preexisting relationship has sex with her and then drops out of her life, albeit tmporarily.

Mar 02 12 - 4:51am

Do it but make a ton of jokes first about how it's going to ruin your friendship forever and how everything's going to be totally awkward afterwards. And then once you're done doing it make more jokes about how everything is totally awkward now. And then hook her up with somebody, quick, and keep making jokes about how things are still totally awkward.

Feb 24 12 - 9:41am

Would it be a one-time pity-fuck, or are you genuinely sexually excited by her? (I'm guessing a measure of both.) If it's more the former: no, never. That won't even be sex, really -- she'll be just as adrift, just as inexperienced. If the latter, maaaybe. Tell her if you're going to do it, it has to be about mutual trust and excitement rather than the mechanics, and if you trust one another and you're excited by one another, then you can talk about it more.

Feb 25 12 - 12:15am

I like this. The right answer is: it depends. I'm just echoing .. , but if you're at all hot for her I say give it a shot. If you're not, it will only feel depressing to you both.

Feb 26 12 - 2:45am
codename v

I like this, too. I lost it to my best friend, also a bit late, and we were genuinely attracted to each other, it was just that the friendship was more important than a losing each other to a failed romantic entanglement. It wasn't always easy, and there were moments of blurred boundaries over the years, but the friendship survived.

Feb 26 12 - 2:57am
codename v

also agree with the people down thread on the following: don't think that somehow it's only going to happen once, and don't set too many hard boundaries - leave plenty of space to talk about both your and her feelings, cause sex does change things, even if it doesn't mean that you end up together. Also, yes you will be doing her a huge favor, I find it immensely reassuring that there are so many posters here who were in my same position. For me it wasn't that I'd lacked opportunities to have sex, it just didn't ever feel right, and by the time I did I was so worried about having that conversation and facing the inevitable "what's wrong with her?" scrutiny that I was having trouble dating.

Feb 24 12 - 9:46am

Its just sex dude. Grow up. You're in your 20's...NOT in High School.
Here is what you do...plan a weekend away some where fun, sun and water. Go dancing...have some drinks...share some laughter and good food. Sex will either happen or it won't as a by product of you two enjoying each others company and being in minimal clothing.
If it doesn't...then you'll both have your answer.

Feb 26 12 - 5:29pm

^this. Perfect.

Feb 24 12 - 10:59am

Do her the "favor" of fucking her. Yeah it will probably the ruin the friendship, but it's one of the greatest things you can do for her. My wife's best friend is a virgin. We're all in our mid-thirties, the best friend is relatively cute, a lawyer (i.e. makes pretty good money), has a good personality....but she can never make it past 2 or 3 dates with a guy. She's spent countless hours with my wife discussing, analyzing, and over-analyzing why she can't find a man.

Ummm, it's because she's a fucking virgin, and guys in their 30's/40's expect some type of physical affection/interaction (please do not interpret this to mean I think sex, of any form, is owed within 2 or 3 dates. I just mean there needs to be some physical connection). Sex has become such a huge hurdle for her, it practically kills any (necessary) flirtation. (It would be a lot easier she was religious and could find one of those guys who's saving himself, but those guys really don't exist in their 30's and 40's). At some point, my wife's friend just needs find some random, and do it. Yeah it will suck, but, imo, breaking down that barrier is far more important than the actual act at this point in her life.

So back to the LW, I say do it. The girl wants to do it, and it's probably holding her back from some pretty great relationships (and another caveat...I'm not saying women need a man to make their lives complete. But love is pretty cool, and it sounds like she might be missing out).

Feb 25 12 - 12:20am

Agree with this 100%. In the same boat. I appeal to the younger set who assume I'm a closet freak, and the older set expect a seasoned good time in their adult relationships. Consequently, I lack confidence and can't flirt with either because it would make me a fraud. And, no one (that I've met) has the patience for this. Doing her this favor would be very noble.

Feb 25 12 - 12:26am

I'm a woman, and I have a friend, mid-30s, also a virgin. (Not a lawyer, though. ;) ) I like your advice, but I also wonder how someone ends up in their mid-30s a virgin. If there's no good reason, then your advice stands. But usually there is a reason: low libido, severe social anxiety, unrealistic expectations, for example. All these problems will also doom any relationship. These women need to figure out what made them not connect until now. I suspect that they aren't that sexually interested in the first place, but sexual interest doesn't have to come from experience (do we not remember when we were 14/15?). It's a tricky situation. Maybe their best hope is finding a low libido guy.

Feb 27 12 - 2:54pm

I'd like to add my perspective here. I'm a woman who lost her virginity at 24, so pretty hold. I'd fooled around with a few people before that but nothing progressed.

I'd like to specifically disagree with your suggestion that these women aren't that sexually interested. I remember being 14/15 and crazy horny... but I had very strict parents. These women could have grown up to feel ashamed of their sexuality, or shamed by men to believe they weren't attractive, or had other extenuating life circumstances that made finding time for a relationship difficult. I think it should never be too late for someone to try, because each of us have traveled a very unique journey through life.

Feb 27 12 - 4:07pm

Thanks for writing, nn. I also think that I was a little harsh. I would love for my friend to meet someone, but although she says that she wants a relationship, too, it's not something that she's actively looking for. It's rare for people to get jobs that they don't apply for, and rare for people to find boyfriends when they don't date. I also think that having no sexual experience in your mid-30s is not equivalent to not having any in your mid-20s. Anyways, thanks for bringing up these other possibilities.

Feb 27 12 - 6:51pm

KH, you're right to point out that there could be something else going on, especially considering my wife's friend is in her mid-30's. The thing that is so interesting/frustrating is the amount of time she spends obsessing over the fact that she can't find a guy (and she really wants children). She's done a ton of online dating. She tries to put her self out there...but this one piece is always missing from the puzzle. She's not stupid, but somehow she can't do the math for this equation.

My best guess is that the anxiety over her virginity has just snowballed with each passing year, and for whatever reason she just can't get past it now. Her parents are pretty religious catholics, but I don't think that's it. In all other respects, she's a very independent and strong willed woman. So I'm pretty much left to conclude that her lack of experience is holding her back.

Feb 28 12 - 8:27pm

I also agree that this IS a hurdle - I did it at 21, which isn't too late - but already felt out of place and insanely behind everyone. And then once I did it, no matter the outcome of the 'relationship', things change for you, you become more aware of the game.

Although to be honest I don't think he should do it. She should get a gigolo or something - safe, he'll teach her the ropes, plus absolutely no way for emotional attachment.

Feb 24 12 - 12:46pm

Don't be selfish. Just do her man. It's the least you can do for a friend.

Feb 27 12 - 11:51pm

Commas, man. Commas. ;)

Feb 29 12 - 11:48am


Feb 24 12 - 1:06pm

I was just in a similar situation as your friend. I was 29, and hell-bent on not entering my 30's as a virgin. While I didn't ask any of my single male friends to de-virginize me, I did set out to get the job done...and I succeeded. I met the guy online, didn't care about him and in some ways I think that made it easier. Your friend just wants to get rid of the label and I totally get that. Here's the thing: if you do have sex with your friend, odds are she is probably going to want to do it with you again so she can gain more experience in a safe and comfortable setting. It sucks to just do it once and then have the dry spell continue. If you decide to do it, you need to consider about whether or not you'd be willing to do it again, because I guarantee she'll want to do it again...and your response to that could affect the relationship more than doing it just once.

Feb 24 12 - 1:18pm

I agree with Erica's advice.

Feb 24 12 - 4:04pm

I, too, agree with Erica's advice.

Feb 28 12 - 6:42pm

WHERE are all these women-who-need-to-lose-their-virginity when I need them?

Feb 24 12 - 1:13pm

As a woman who actually did this, I don't regret it. My friend and I are still friends, and I'm less nervous about approaching men because I don't feel any need to tell them that I'm a virgin, and I don't need to worry about the outcome of a conversation like that. She's a grown woman, and hopefully, she's really thought this through before asking (you should talk to her about it to make sure), in which case, she knows what she wants, so why not?

Feb 24 12 - 1:36pm

This woman doesn't know what she's asking of you and she doesn't know how she's going to feel afterward. She wouldn't ask unless she already felt close to you. That first time is only going to bring you closer. Unless you're awful in bed, she's likely going to want to do it again, and why bother going out to find it when she can just come over, hang out, and get it on. No matter what she says (or even actually thinks) this will turn into a relationship. If it does and you don't want that, then your rejection is going to hurt her. Or, it may turn out that you really fall for her and she keeps to her word that it's just sex. Bottom line - unless you're prepared for it to turn into something more than just one friend helping out the other friend, I'd pass on this one.

Feb 24 12 - 1:55pm

She's dead wrong if she thinks it will be a learning experience only. Feelings always get involved. But that doesn't matter, the friendship can survive it, as long as neither of you think it's going to happen only once, or that it will solve her problem instantly.

Feb 24 12 - 2:25pm
Voice of Reason

You haven't really said anything about how you feel about her other than the fact that she is an old friend. Are you ok with the fact that she doesn't have any feelings for you, or do you want more but feel stuck in friend territory? If the latter, are you holding out hope that if you do this, she will fall fabulously in love with you? Or, even worse, are you holding out hope that by asking you this, she is revealing her TRUE feelings for you?

Even if you can pull this off and stay friends, will that be enough for you?

Feb 24 12 - 2:29pm

Had a similar dilemma with a male friend of mine who wanted me to de-virginize him. He was 25. I didn't do it. I knew he sort of had some kind of feelings/attraction to me, and I didn't want to lead him on. It didn't matter, though. Things got awkward after that and we don't keep in touch.

Feb 24 12 - 2:32pm

I'd give my right nut to be you,you lucky bastard.

Feb 24 12 - 3:06pm

How about you offer to go on a holiday and be her wingman ? You know some skiing some mulled wine and she'll probably feel safe and more adventurous. No need for you to get more involved than that if it hasn't come naturally.

Feb 24 12 - 3:24pm

Can't believe the dialog of the letter or the replies. Why do you (or anyone) have sex? You have it because you have an attraction (hopefully mutual) for the person and you feel safe physically and emotionally. All these other comments about 'doing it with someone she doesn't love' 'didn't want to lead him on' etc, is just quid-quo-pro; one or both parties want something before or after sex that is culturally induced. She's already told you she feels safe with you physically and emotionally. Now you're trying to leverage something by using your crystal ball and seeing how you both will feel in the future. Accept the fact you can't see into the future and you can't dictate to her how she will feel. Right now you haven't said you don't feel attracted to her you only say you fear your crystal ball gazing.

Feb 27 12 - 4:17pm

Excellent point

Feb 24 12 - 3:25pm

I would love to know the ages of the people who have responded to this. As one poster mentioned you are NOT in high school. She is not in high school. The idea that she will want more than friendship with you after having sex because you "took her virginity" is ludicrous. She's not a child, yes, in spite of what some may tell you, she does not have to have sex to be a grown ass woman who knows what she's doing. It sounds like you are making a bigger deal of this than she is. The first time you have sex is, for most grown-ass women (and I've known a few who were virgins into their twenties) not substantially different from any time you have sex. If you think that you couldn't handle it, would develop feelings for her, feel awkward around her, etc, then don't do it. She has made it clear that that will not be a problem for her. Think of this way--If she were not a virgin, and was propositioning you for sex, would you do it? If your answer is hesitant or no, don't do it. If your answer is a clear yes, do it.

Feb 25 12 - 5:15pm

Best advice on the board. The 26-year old virgin has her head figured out, so the only head could get messed with is yours. Figure out whether it will or not, and act accordingly.

Feb 25 12 - 6:11pm

A caveat to the above: the advice only applies if this woman is indeed someone who in general has good judgement and knows her own mind. If she's flaky, unpredictable, or prone to making bad decisions in general, then trust your instincts and say no. As one of her oldest friends, you should have the information to make this call.

Feb 24 12 - 3:26pm

Do it if she's hot.
Don't if she's not.

Feb 24 12 - 3:29pm

I think the deciding factor here is how you feel about her. If you have some romantic attraction/curiosity, then you may as well go for it. Feelings will get involved, but the outcome is uncertain, and may be positive. BUT, if you do NOT have any romantic feelings whatsoever for her, then don't do it. In that case, the outcome IS certain - she will be hurt by your "rejection" afterwards, and you will be pissed that she "mislead" you into thinking you'd be in the clear afterwards. Sex brings up emotions we swear we didn't have beforehand. Even those who are experienced with sex will frequently get blindsided by this fact. As a virgin, she is in no position to make promises about how she'll feel afterwards. Remember that.

Feb 24 12 - 3:39pm

If you're attracted to her do it! She's disease free and willing.

Feb 24 12 - 3:43pm
mr. man

there's no such thing as 'strings-free sex' even when we try to make it so. there's always a 'before' and 'after' aspect to a friendship that goes horizontal. that said, i'd probably do it. she could flake on you afterward though. it's a definite possibility. this is sort of a beautiful trap.

Feb 24 12 - 3:55pm

i was an older virgin. i had a few opportunities to have sex with guy friends and i wish i would have. guys i just met assumed i would love them forever if they slept with me. i ended up having a one night stand with a friend of a friend who was in town for the weekend. i really wish it had been with a guy friend. i have enough experience to know now that sometimes you have sex with a friend and things get weird for awhile but go back to normal later. sometimes you guys can't hang out again. it's a total crapshoot, but one possible outcome is you free her up to be available to other people (she could freak out/fall in love with you). if you do it, i would say you should plan to hang out the next morning and then spend some time (a week or two) apart, tell her it will feel weird but its for the best. the other advice is that you probably don't want to do it because you wrote to nerve about it. i would listen to that.

Feb 24 12 - 6:36pm

Post her contact info and i will take care of it for you / her. I will even do you a solid and make it into a video, for educational reference of course..

Feb 24 12 - 7:09pm
Friendly advice

Give her the experience she wants and take your time to do it right and do it well. Losing your virginity and the emphasis we place on it (especially for women) is vulgar. She is already feeling lost, left out and lonely. Popping her cherry, getting up and going back to being friends will leave both of you feeling used and ruin the relationship. Instead, explain losing your virginity should be a process that empowers her and brings her into her womanhood. Prepare a curriculum and break it down by lessons over a long weekend. Think about what she has done sexually and what she has left to do to feel that she has blossomed. Does she masturbate, has she given her self an orgasm? Has she ever been nude in front of a man before? In front of you? Has she given a man an orgasm? Given or received oral sex?

There are a lot of steps before intercourse that are still part of sex and understanding your sexuality. Help her completely and repeatedly and you might just keep your friend. Pop her cherry and move on and your friendship will dissolve. Do nothing and your friendship is already over.

Feb 25 12 - 9:20pm

This is a very pretty answer.

Feb 27 12 - 3:08am

"Explain losing your virginity should be a process that empowers her and brings her into her womanhood."

Ideally, sex should always be empowering for all parties who are having it. But explaining that it will "bring her into her womanhood?" Eww! First, that notion implies that something is wrong with the woman friend--that she is now a "little girl" who can only be a grown up if her friend deigns to use his big, strong penis to transform her. Second, the "come into your womanhood" notion is condescending in that it tells someone what sex should mean for them. No one should tell anyone else what sex--the first time or anytime--ought to mean for that person, not even a sex partner. If the LW has sex with his friend, he can tell her about a few things that she might expect physically, but he should not presume to tell her how the experience will really make her feel otherwise.

Feb 27 12 - 11:54pm


Feb 24 12 - 7:39pm

Do it. As a girl who lost it in her twenties, I was pretty much in the same spot, feeling kind of old, desperate, and left out. I went home with a bartender, but I think getting it over with with a friend is much better. Just because she's a virgin doesn't mean she will love you forever, and it'll be something that she'll probably be very happy about.

Feb 24 12 - 9:45pm

Life's too short. Have sex and be happy.

Feb 24 12 - 10:30pm

I had a close friend who I used to hook up with but then was just friends with for a long time and I lost my virginity to him at 22 one random time we hung out. It was sort of huge mistake because I had feelings that he didn't share and now we no longer speak. Sure, everyone is different but it isn't that helpful to have sex one time with someone. I don't think it's better than her finding someone she might actually like. Especially since she just wants to no longer be a virgin...she probably won't feel that much better about herself. And if it really will just be a one time thing. I doubt she'll feel much more experienced. And it probably will alter the friendship in potentially negative ways.

Feb 25 12 - 12:52am

Just do it. And do it right. Her virginity has become a stumbling block for her. Help her get over it. Just make sure there is lots of communication and lots of foreplay. Do it respectfully and tenderly. make her first time better than it would be if she got drunk and did it with some random guy. It could be a happy, lifelong memory for her. Be a friend and do it.

And take half a Cialis, just in case you get nervous.

Feb 25 12 - 2:09am

No matter what, be honest and respect her feelings. If you genuinely can't bring yourself to bedding her, then DON'T & let her know that in no uncertain terms. Of course life is meant for adventure and exploration. You will regret more often what you didn't do, more than what you did. I can't say what I'd do if I were in your shoes 'cuz I've never been there. You're both adults who have been friends for a long time, based on your tone. I vote for taking her out for a nice dinner, showing her a good time BEFORE you progress to bedroom activities. If she's game, plan a weekend of togetherness in which you may seduce her by Saturday night or some time Sunday. When it comes down to it, it's better to start as friends before you venture down that bedroom path, so you got that part already covered. Give her a try.

Feb 25 12 - 11:46am

I took the virginity of a male friend at college graduation. After the graduation party, we were sufficiently shitfaced and put on some Coltrane and played. After some hours of exploring, we did the deed. Of course, it was fast. So we did it again. I feel like I did a good deed for the ladies (hopefully) to come in his life. We still think of each other fondly, though are rarely in touch.

Feb 25 12 - 9:48pm

I just took the virginity of one of my close male friends. We're undergrads and before the event (and now, after it) our relationship was platonic. He didn't explicitly request me to devirginize him; it just happened. It was fun and even though he had some trouble, I tried to help him as much as possible and make it a good time. Knowing he was a virgin and being close meant I was more understanding than a random girl at a party for example, or worse, another virgin. Now he can explore without having that extra stigma hanging over him.

Conversely: when I lost my virginity a few years ago to a guy I barely knew, it was super shitty. Granted, there's an age and maturity difference, but I suspect it's about the same. While losing it in a committed relationship is ideal, a good, experienced friend that's sexually proactive and expects nothing beyond the one night (although is open to developments) is also a good option. If LW does it, which I think he should, he should only do so if he's fine with the possibility of a relationship or FWB situation happening.

Feb 25 12 - 12:22pm

I lost my virginity with my best friend when i was 17. We didn't had any feelings other than the friendship and we've known each other since we were 11. It happenned again a couple of times and we're still great friends. I say do it. The friendship will not be lost if you don't want to. She sounds like she's ready and she wants YOU to do it. Maybe she thinks other guys will be freaked out if they know she's a 26- year- old virgin and she thinks she can trust you. I don't really see the problem.

Feb 25 12 - 1:13pm

I think your friend is an asshole for thinking that virgin is a bad thing. Just like the conservative side(of sexuality) who believe in waiting until marriage for sex(which is ok if thats what you want to do!) your friend is being stigmatized by the liberal side(of sexuality) that she's a freak if she hasn't had sex. She just needs to stop worrying about it.
From my experience, YES when you are a girls first she's going to be all over you if you are her first. Its a powerful thing. I was attached to my first for a while.
Short story- talk to her more about it. set rules. some will be broken. but if you are going to do it you have to turn your emotions off after wards. I don't know how you can during, but after you have to keep that state of mind and not bend.

Feb 25 12 - 8:09pm

fuck her gently, dude.

Feb 26 12 - 10:32am

Drill Baby Drill

Feb 26 12 - 12:57pm

Just beware. I slept with one of my best friends recently. I thought it was a drunk fuck. Turns out the chemistry was so intense, and it's happened a few more times since then. My world came crashing down and all I can think about is him now. Problem, though he's fresh out of a LTR, I'm totally ready for an LTR. Sure we've talked about it, and we're mature enough to deal with the repercussions. Just a reminder, you NEVER know what you're getting into.

Feb 27 12 - 6:46pm

Yes, this is a risk whether either of you is a virgin or not. When it happened to me, I was the one fresh out of the LTR and we had an understanding that I did not want more than some occasional play. That wasn't enough for her, and now we rarely speak.

Feb 26 12 - 1:20pm

In the future when you are tied down and lamenting all the ass you passed up this will haunt you. Hit that ass!

Feb 27 12 - 7:36pm

I would've phrased it differently, but basically this. Either that or a frank discussion with your friend about her misguided emphasis on virginity and sexual prowess.

Feb 27 12 - 8:16pm

Dude, if you happen to be gay, don't be forced into it. It's not likely to be a good experience for either of you, and it could indeed wreck a friendship.

Mar 27 12 - 7:28pm

I wondered the same thing, RW!

And, I agree, it's not worth having sex with your friend if you happen to be homosexual. Aside from what that means for you, it's probably not good for her either, especially because she is so emotionally torn down by her virginity. If you are so inclined, you could try to help her understand her sexuality and virginity and be her stand-in shrink, but she can also pay someone to do that. It's probably better for her to solicit a heterosexual friend for this charity.

If you aren't gay, though, it is my suspicion you would have already had sex with her if you wanted to. As one commenter already said, you have your answer because you wrote this letter. Don't have sex because you feel bad for her. And not because it cheapens sex or gives her a bad impression - that doesn't matter. I think you shouldn't do it because it seems like you (simply) don't want to. As harsh as it may seem because she is your friend, her problem is not your problem. All of these other commenters' experiences have nothing to do with you and your friend.

Feb 28 12 - 12:46am

Everything changes the relationship. Relationships don't stay the same. Every word and minute people spend together, something changes. Go ahead and give your friend that wonderful gift. You taking time to think about it suggests that you'll give her an above average experience. Sex is not this thing that should be hidden away in a cabinet for a special day for in the future. It's unlimited and free. Enjoy and indulge.

Feb 28 12 - 12:47am

Everything changes the relationship. Relationships don't stay the same. Every word and minute people spend together, something changes. Go ahead and give your friend that wonderful gift. You taking time to think about it suggests that you'll give her an above average experience. Sex is not this thing that should be hidden away in a cabinet for a special day for in the future. It's unlimited and free. Enjoy and indulge.

Feb 28 12 - 12:25pm

DUDE TAKE HER TO POUNDTOWN!! I have many friends that are girls that I have hooked up with, I feel it could bring you guys closer together. Make it really nice for her and shit, be all sweet and gentle, she will be ever grateful it. I have long friendships with these girls after and it is always fun to joke around about hooking up in the past. She is a grown woman who is in needs your, your not being a good friend by denying her.

Feb 28 12 - 12:34pm

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Mar 01 12 - 1:35am

In my experience it's the friends I didn't sleep with and wanted to (or vice-versa) that dropped away. The ones i slept with are fine. :)

Mar 01 12 - 3:55pm


Mar 01 12 - 2:05am

I had a surreal experience with something like this, for four consecutive winters when I was younger I had a girl ask me to do the same thing. I took up the offer once out of the four times out of fear of ruining relationships(one was a proper relationship,). The other times I felt just out of place and uncomfortable with the situation on a moral level, one involving alcohol for instance. This doesn't sound like your situation.

Ties have been completely lost with all of them over time, the sexual tension is what makes things awkward-not the sex itself from my experience. Better it be someone she trusts than some random creeper in my eyes. If she's already asked you she can't really retract the statement you know? It's out there, be a good friend and keep her from making a worse decision.

Mar 02 12 - 4:58am

Set up a website and help her auction off her virginity. Make it profitable in lots of ways. Virgins are hot commodities, man! She doesn't know the goldmine upon which she sits.

Mar 03 12 - 9:39pm

I found myself in a similar situation a couple of years ago. I was 29, and I wanted to lose my virginity really bad, so I got myself into a relationship with someone, and I lost it. Believe me, when enough time has passed, you begin to think about your virginity in scientific terms. As someone said up there, you begin to get obsessed by it. Not everybody has the luck to do it with someone they love. For me it was not ideal, but it was fun. And doing it with someone you know beats doing it out of desperation with someone you just came across at some pub.

Mar 09 12 - 12:24am

Don't do it. Losing one's virginity should only happen with someone you love; it should be very special, especially when someone has waited this long. She will deeply regret wasting her virginity on someone she doesn't love or isn't attracted to. She should keep waiting until she finds the right guy, someone she loves, who loves her back, & who understands what a big deal this is. You can only lose your virginity once; better to wait until the right guy & the right time. I can't imagine wanting to be rid of it; that is backarsewards.