To Wait or Not To Wait

February 2, 2009 7:38 AM

I always thought I'd wait for someone special to have sex for the first time. But I haven't met anyone special. Is pursuing a casual relationship a good idea, and how do I do it?

I'm a 25 year old female who is and always has been single. This is something I'm generally happy with - I have a very successful career, a loving family, wonderful friends, and many hobbies that I find challenging and fulfilling. Whenever the possibility of dating someone seriously comes up, I find myself balking at the idea.

It's not that I'm ruling out a relationship - there have a half dozen people I've met in my life who I absolutely would have loved to have dated seriously, but things never worked out (for several, low self-confidence meant I never told them how I felt; the last guy I really liked chose someone else over me). But I generally don't think it's worth my time unless I really feel a spark. And I rarely feel a spark.

That being said, I do really feel like I'm missing out on one key aspect of relationships - the sex. I mean, I hear it's a really good time. ;)

I'm a virgin. And not an everything-but virgin. I'm pretty inexperienced in general. I've always assumed I would wait until I was in a real relationship. But I don't want a relationship right now and I do want sex and it just seems silly to wait, you know?

When I try to define what I'd like, the terms that come close are "casual relationship" and "friends with benefits". I don't want a string of random encounters because a) that doesn't feel safe to me and b) I would like some emotional intimacy along with the physical intimacy.

However, I have a whole bunch of questions. That's where you come in, AskMe! Please answer any/all of these, or just supply advice/stories/opinions you think would be appropriate/helpful:

~ Is my picture of what a FWB/casual relationship is accurate? Ideally, it'd be a relationship or a series of relationships where we saw each other every once in a while (no more than a couple of times a week, no less than a couple of times a month), knew a fair amount about each other and were friendly and affectionate towards each other outside of the bed, and would sleep/cuddle with each other in addition to having sex. Is this achievable, or is it a totally unrealistic picture?

~ I also imagine the people that usually do this are usually pretty experienced. Would someone even want a FWB arrangement with someone they'd have to teach to be good at it? Also, I know there are a lot of potential land mines out there for relationships like this in general, but any specific to someone who's previously been a virgin?

~ How does one go about setting this up? Should I approach male friends I am attracted to but not close with? (I have no desire to complicate a good friendship with this, but I have several new guy friends and I meet new ones all the time.) Should I try online? (I have reservations about that.)

~ I can't 100% get over the hang up that my first time should be "special". I'm not so sure it's an internal hang up, though - the thing that gives me pause is thinking about how I would explain it to others who ask about it. (This is also the problem with doing this online, so maybe I should just get over worrying what other people think about me.) Is there any way for me to be more sure that this is the right move?

For what it's worth, I am pretty emotionally mature. I can be honest and straightforward about my feelings, and I understand that human emotions and attractions are capricious and that in the end everyone's just gotta do what they gotta do, and not take it personally. And while I do not want to be hurt or regret this decision, I feel pretty confident that even if it turns out to be a bad idea, I'll be all right.

posted by anonymous to human relations (24 comments total)

If you relax your very high relationship standards enough to see people casually, it's possible that one of them will turn out to be someone special. What's special about a person isn't always apparent right when you meet them, and sometimes sex is the language we speak to explore what kind of connection exists between us and another human.

I wouldn't pursue a FB per se, just stop looking for great cosmic signs that THIS IS THE RIGHT PERSON. Loosen up, explore with people you're intrigued by who normally wouldn't register on your significance scale.

Your first time is special because it's YOUR FIRST TIME. It has value to you, as an experience, regardless of who and where and when (and trust me, no matter how "special" it is, you'll look back one day and roll your eyes).
posted by hermitosis at 7:44 AM on February 2 [2 favorites has favorites]

I would like to explode the myth of the "first time". You say you have many hobbies, so think about the first time you did each of them. Watch other people the first time they plan tennis, or pick up a violin. Watch kids the first time they read a book. Despite what everyone wants to believe, sex isn't that different. The first time you do it, you probably won't be very good at it.
That doesn't mean it won't be fun! Sex is like pizza: when it's good, it's great, and when it's bad... it's still pretty good.
posted by crazylegs at 7:53 AM on February 2 [1 favorite has favorites]

You should know that except in very odd special circumstances, it never really feels good for a woman the first time. It will have considerable meaning for you, but physically it's almost impossible to truly enjoy it. At least for me, sex was one of those things that got better with practice, and the more my body became accustomed to these new sensations, the more I was able to learn to embrace them and just have a great time.

On that note, I would suggest at least waiting until you meet someone that you can feel close to. Maybe that "spark" won't be as spectacular as you might have wished, but at least you'll be able to have a special experience with someone that you trust and you'll be comfortable expressing what you enjoy and what you don't enjoy.

I think your real problem is being open to a real relationship, due to your above named issues, so if you want to have a fun sexual experience, just find someone you trust and care about and enjoy experimenting. If the relationship goes anywhere from there, great. If not, that's ok.

You really shouldn't build up that first time as such a physically fulfilling experience - more often than not it's quite awkward and even uncomfortable. But practice makes perfect!
posted by Grimble at 8:04 AM on February 2 [1 favorite has favorites]

If you want to contact a mod to update the thread with a throwaway email address or contact me directly via MeMail, please do. I'd be happy to share my experience with this.
posted by meerkatty at 8:18 AM on February 2

Just start dating someone and if it feels right do it.
posted by xammerboy at 8:43 AM on February 2

Sex is like pizza: when it's good, it's great, and when it's bad... it's still pretty good.

GOD, I wish people would stop saying that. For real. I've had some terrible sex and even worse pizza. Saying this kind of stuff just makes people go for quantity rather than quality of both, and that just makes us more likely to be fat and STD ridden.

Anon, here's my advice to you: FWB is difficult to manage at best and results in a loss of friendship at worst. Even if you consider yourself very emotionally mature, it may be really difficult to deal with the slightly detached emotional at the same time as the physical. I think you should try giving dating a try more than a FWB setup. Get to know new people people on these dates. Most likely you will know when you are ready to have sex for the first time, because the idea of sleeping with them wont be scary or weird. As a side note, anyone who pushes you before you want to have sex with them is probably not the kind of person you want be sleeping with.

One thing you may want to consider is if you want to disclose your virginity or not to the other person. I think it's the kind of open communication that you may want to have, but I've known girls that didn't disclose and they felt okay with it as well. Interestingly, once the guys found out they were the girls' first, they felt guilty that they had not made the first time more special).
posted by piratebowling at 8:53 AM on February 2 [8 favorites has favorites]

Seconding meerkatty. E-mail in profile.
posted by phatkitten at 8:54 AM on February 2

You are making this way too complicated. If there's a man you're sexually attracted to, flirt with him. See where it goes. It might turn into FWB. If so, great. It might turn in to that real relationship you've always been looking for. If so, great. Maybe it doesn't work out. If so, you've learned something. If you're averse to trying it with strangers, then, sure, try it with male friends in your circle of acquaintances. I'm pretty sure that's how most people meet other people.
posted by creasy boy at 9:00 AM on February 2 [1 favorite has favorites]

I agree that it may not be the most pleasurable experience the first time you do it, but I don't think it's any less special. Sex is about intimacy, vulnerability, trusting and sharing.

I waited a long time before having sex. I don't regret it. I knew that I was inexperienced and that the first few times would be frustrating and a learning experience. It meant a lot to know that the person who I was with was patient, caring and trustworthy. In other words, he was (and still is) pretty special, and he was worth waiting for.
posted by bristolcat at 9:00 AM on February 2

Is my picture of what a FWB/casual relationship is accurate? Ideally, it'd be a relationship or a series of relationships where we saw each other every once in a while (no more than a couple of times a week, no less than a couple of times a month), knew a fair amount about each other and were friendly and affectionate towards each other outside of the bed, and would sleep/cuddle with each other in addition to having sex. Is this achievable, or is it a totally unrealistic picture?

That's a boyfriend.

In your situation, I'd suggest you go for the whole dating/boyfriend enchilada. You want it to be special which is entirely reasonable. First times aren't perfect, but they can be special. You don't have to wait for Mr Perfect, but start looking/flirting/dating and see if you can find someone you really like.
posted by 26.2 at 9:29 AM on February 2 [2 favorites has favorites]

1. Your vision may be doable, but could be elusive. In my experience, FWBs just kind of happen as opposed to being planned things ("Hello, I would like to propose an FWB scenario to you"). And they are a balance that teeters. By that I mean that they often wobble and fall into one of the following buckets sooner or later: just friends, hurt/enemies, relationship. What often happens is a mismatch in expectations. You, for example, want cuddling and want affection outside the bedroom. Here is where guys being guys may interfere. He'll be happy to have a reliable booty call if that's what he's looking for, but if you send off nesting signals that he interprets as you trying to draw him in, it may trigger his don't-get-tied-down reflex and he'll start acting weird and his cell phone will start "acting up" and "missing calls." It's entirely variable, but that's a common scenario.

Your first attempt at this may reveal to you whether you can really handle a non-relationship situation. Your hypothalamus wants to bond, and as much as you may want an FWB, you may find that things operate differently once you've shared the most intimate and vulnerable thing you can share with another human. Why doesn't he call? Couldn't he just call? Can't we just go to lunch or a movie? That's when expectation mismatches can start to crop up and people get hurt, usually you. I've found myself on the other end of that. Everything seems cool and we seem to have an understanding, both seem to want the same thing and be cool with it, and then she starts morphing it into an exclusive relationship and I start to feel boxed in and try to extricate myself without a big blow up. And that causes a big blowup and she's hurt and I'm the goat and gaaah! I'm just saying, it's very tricky, and it can be hard to separate sex from the emotions it very much wants to be paired with. People are designed to bond!

2. If you have a vagina, you're in. Don't worry about the experience so much. The penis has only one directive: GET IN THERE. Different people like different styles and activities once things start moving, but as long as you seem to be into it, you're probably going to be just fine. Google for a few basic tips if needed and otherwise just enjoy yourself, and himself. Use your body more than your mind. Confidence is sexy too, btw. Self consciousness isn't.

3. As opposed to trying to set up an ongoing scenario from the start, with terms and conditions as cited above, an easier way to set this up might be the organic route by which they usually occur. Just make yourself available one time up front when you are out with friends. Basically, go out and flirt with the guy of interest and send off "the signals." Be 85% obvious, but not 100%. Drinks help. Let yourself get picked up. His place, your place, whatever. People do this.

So, having done it once, he knows there's a good chance he can count on you again. Here's where it may pay to be "cool". You keep it on the down low, you don't tell your friends, you don't try to call/email him or wait around for him to call. "It was just a thing." You don't show up at his place or try to bring him food or something nesty/clingy. The next time you see him, you're "cool". Maybe a knowing glance, a half-seen smoky smile. But nothing too overt. A bit of mystery. He's thinking, "Whew, she's not going to put the thumb screws on me. And I think that door is still open. Wait, is it open? Was she throwing me vibes just now? Was that just a one-time thing?" Let your attitude make it a bit ambiguous because that imparts some spice/wonder/mystery and sets up a little challenge in his head, whether he knows it or not. Sometimes no challenge means no need to try again. So there it is hanging between you, unspoken, but you don't release that useful tension by acknowledging it. You want to send the message that, hey, you're still separate individuals in the group and can still go out and have a good time without issues or expectations or guilt. Next time you're out together in a scorable scenario, be less obvious than the first time. You're just out having a good time - maybe I'm going home with someone and maybe not (and maybe you don't get together again the very next time - be patient). But maybe as the evening progresses, a little glance here, a private quip there, and things start heading in that direction.

Half the fun of FWB is sneaking around, and I think that's also part of what can sustain it. You two leave the party and people don't make the connection that you're going to wind up together that night. Maybe people suspect something's going on over time, but don't really know, etc. Once it's out in the open, there can be pressure to go one way or another. Because at that point, people are like, "So she's your regular fuck, eh?" or "God, she just lets him come over and do her and never makes an honest man out of him. How sad. She must have self-esteem issues." or "So are you guys dating? Why didn't he take you to that wedding? Are you all going to start hanging out more?" None of that happens when nobody knows for sure you're getting it on behind closed doors. That's just my experience. People may get it eventually but the less you talk about it the better. It's sort of not a natural situation and requires special handling.

Once it has happened twice, you're likely set to keep going, assuming you both like it. Be prepared for it to not last forever. These things come and go.

4. In my experience and in all of the anecdotal evidence gathered from others over the years, the first time is, in hindsight, more something to just get out of the way rather than store up for that special perfect moment. Even people who wanted it to be super special and arranged everything just right usually ran into the physical realities of it and it didn't meet expectations, guys or girls. Just find a guy that makes you hot and go do enjoyable stuff together. Over time you'll get a better idea of what you like and that's when it can be a lot better than any imagined perfect first time. But as you've seen in this thread already, some women are glad they waited. So do what feels right. Good luck.
posted by Askr at 9:30 AM on February 2 [1 favorite has favorites]

piratebowling is right: there's bad, bad, bad sex out there.

The rest of it's right, too, but I'd add to the final paragraph that some guys get really weird when they know someone is a virgin. It goes from making promises they can't keep (or may not even intend to keep) to obsessing over being the first in a weird, slightly uncomfortable way. Even people who seem extraordinarily emotionally mature can do this.

Listen to bristolcat, Grimble, xammerboy, creasy boy, 26.2, and hermitosis, too. And the part where crazylegs says to think about your first time with other pastimes is right on - you're going to be just figuring all of this out, so don't overload it with expectation.

Whatever you do, experience the experience as you're experiencing it. I know that sounds redundant, but I know so many people who have built up all kinds of ideas in their heads about how it's going to go, what they should do, what it will feel like, what the other person is going to say, and all kinds of other stuff that ends up being baggage at a time when feeling unburdened is a great aid to having a truly enjoyable time.

And, listen, it might not be enjoyable. It might hurt too much or you might get overwhelmed or any number of other things. Don't let that psych you out. Be prepared for these things. If the person you choose is a gentleman, he should be willing to stop and do something else if it gets too much.

I do know women who had an amazing first time. They were all 18+ and had some idea of what they would be getting out of it and had partners who knew how to focus on someone else's pleasure. I think those are the most important things you can go into this with.

Whatever you do, I wish you luck in having the time of your life!
posted by batmonkey at 9:30 AM on February 2

As an also 25 year old virgin of the other gender (I seem to bring this up a statistically significant amount of time lately. I guess I can only answer what I know about!) I can't really give you much advice. I did have a Friend With Benefits though, just that none of those benefits involved intercourse. Anyway I'll try to answer each of your 4 points as best I can in case I can offer some insight.

-If you have ever seen the Seinfeld episode where Jerry and Elaine attempt a FWB relationship you can see how things can get complicated. The issue being that for many people it can be difficult to a)be friends with someone, b)sleep with them regularly, and c)not grow to desire more than the other person desires (that is, you find that you only want to be with Guy A, but Guy A isn't interested and just wants to fool around). My feeling from watching that episode was that you should try to remove the sex act and physical intimacy from emotional intimacy as much as possible. When Elaine came up with the rule "sleeping over is optional" George told Jerry that they "got greedy". Try to be clear about the boundaries and maybe come up with some of your own rules to prevent that from happening.

-I wouldn't say it's guaranteed that a guy would avoid a girl without experience. While some wouldn't go for it, I bet there's TONS of guys who would get a kick out of introducing a girl to the ways of sex. I'd like to do it, but that would be like the blind leading the blind and I can't imagine it going too well.

-How it worked with me and my FWB was that she said she wanted to go out with me but I wasn't really able to see myself dating her as we had known each other since childhood. Then she suggested FWB instead which I was able to see myself doing with her. I think if you want to set this up you can either go directly into it and just say "hey, wanna do this?" Or maybe bring it up as a topic of conversation. "Hey remember that seinfeld episode?" and then let the conversation take its course. "Oh I could see myself doing it, but only with the right guy" and then jokingly go "Hey, we're both single! Why shouldn't WE do it? ha ha ha. Now that I think about it..." and so on.

-The only one who knows when you want to do it is you. I assume you meant your "first time" when you said you weren't sure what to say when people "ask about it". Just be honest. "I got a late start and I decided that this was an experience I wanted to have so when an opportunity came up with an acquaintance I took it." and if someone judges you for it you don't need them in your life.

Hope that helps.
posted by Green With You at 9:34 AM on February 2

But I generally don't think it's worth my time unless I really feel a spark. And I rarely feel a spark.

I think you should revisit that one. Generally, these things aren't all or nothing. Just go with the flow and see what happens.

Here is what I recommend, in a very 1, 2, 3, 4 concrete steps way.

(1) Start by learning to smile at boys. When you smile at them, they will smile back and you will respond. Best to practice by smiling at plants for a day, then animals on the street, then strangers.

(2) Learn to flirt more. The one thing I cannot emphasize enough for members of both sexes, is eye contact. Practice having an entire conversation with someone while maintaining general eye contact with them. It doesn't mean stare at them, but generally, while talking, look into their eyes. (I told a female friend about this and she called back a little while later amazed how easily it worked).

(3) Learn to compliment. If a dude is wearing something nice, just say it.

A little voice inside you may scream that you cannot do this, that this is impossible, no way. Do not listen to that voice. If something tells you a person is not right for you, then listen. But don't listen to any voice inside your head that tells you that you could never do any of these things.

I also do not believe that you must have bad sex the first time. I'd buy one of those how to manuals. When I was in high school I'd always look at those books every time I got a chance, especially "How to Make Love to A Woman." (CHEESY! I KNOW!) I found out where every thing was located and what women who responded to interviews in those books said they liked. I know they have similar books for women. When it first happened for me it was a one-night stand and the person in question later made complimentary statements to third parties.

(4) Learn to like yourself. How to do? I suggest the CBT exercises in Feeling Good or Intimate Connections, two bosoks by Dr. David Burns. Burns stuff works, plain and simple. Its like those seduction systems, but without all of the mysoginist crap and cutting people down.

(5) Control for process, not for outcome. Usually not a problem for women, but look at each potential flirting encounter as a chance to learn how to do something better, not a chance to meet your first boyfriend or one-night stand.

As for general advice, find yourself a boyfriend. It doesn't have to be a "I wuv u" thing right away, but general dating where the guy genuinely likes you and because of that wants to make sure that you are as happy as he is with everything. Take your time. We have powerful emotions that sexual contact stirs up and you need to know that ahead of time. It sounds like you really haven't felt those emotions. They can really, really cloud your judgment in ways you really can't percieve very well. So be careful, please.

Oh, and sex is really, really fun. Yes you will like it. A lot.
posted by Ironmouth at 9:59 AM on February 2 [1 favorite has favorites]

Just a quick neuroendocrine warning about sex. Beware the oxytocin. Oh, it's just the little neurotransmitter that facilitates pair bonding, and petting and orgasm in women lead to spikes in our friendly chemical. It is also released during the contractions of childbirth, and may be responsible for the pair bonding that encourages female mammals to nurse their pups rather than leave them in a ditch. YMMV. Although males are clearly capable of pair bonding, they do not experience this same spike in oxytocin upon (ahem) vaginal stimulation.

Why should you care? As piratebowling pointed out, sex can be very bad. But if it is good, there is a high chance that you will experience the oxytocin rush and pair bond to your mate, relationship status be damned. It happens to the best of us. I've experienced it, and I've seen it with my friends. A male and a female go to bed as friends. Sex is good, and afterwards the female feels much more affectionate towards the male, while the male feels exactly the same as before. It's an unfortunate biological asymmetry. We live in a post-Sex-in-the-City world where women can do as we please sexually, but I've still seen 80% of "casual" encounters get incredibly complicated, and it's usually the woman who seeks something more.

So I guess I'm saying that you might as well hold out for a relationship. You'll get to have sex multiple times, and it will get better and better. You'll have all the good stuff - cuddling, affection and a partner to share your feelings with. If it's sexual stimulation you seek, it's much tidier emotionally to invest in something that goes bzz in the night.
posted by ladypants at 10:23 AM on February 2

Other than committing to exclusively sleep with one another (something you probably would want for safety reasons) the things you want are the backbone of a relationship. If you're willing to drop your standards enough to let you sleep with someone "unspecial", you should just drop them to let you date someone "unspecial".

I should also note that the relationship I'm in right now started out with someone who really didn't seem that special. I was attracted to her and I knew her as someone I worked with but once we actually got together and spent a little time together, man was she ever something special. You can only know so much about someone until you actually emotionally invest in one another; perhaps its your time to take a chance on someone.

Good luck!
posted by David Fleming at 10:28 AM on February 2 [1 favorite has favorites]

You'd think this would go without saying, but don't do it with a guy who won't use a condom.
posted by aquafortis at 11:06 AM on February 2 [1 favorite has favorites]

~ Is my picture of what a FWB/casual relationship is accurate? Ideally, it'd be a relationship or a series of relationships where we saw each other every once in a while (no more than a couple of times a week, no less than a couple of times a month), knew a fair amount about each other and were friendly and affectionate towards each other outside of the bed, and would sleep/cuddle with each other in addition to having sex. Is this achievable, or is it a totally unrealistic picture?

What you describe here? That's a relationship. Or at least, that's MY relationship. Fuckbuddies are more casual than that, or at least mine have been. Friendly, yes. Affectionate, no. Affection is closely connected to relationship status, and if both people are avoiding that level of entanglement, often affection out of the bedroom is eschewed in favor of maintaining independence.

~ I also imagine the people that usually do this are usually pretty experienced. Would someone even want a FWB arrangement with someone they'd have to teach to be good at it? Also, I know there are a lot of potential land mines out there for relationships like this in general, but any specific to someone who's previously been a virgin?

This is a little tough, and not being personally acquainted with lady-parts I am not exactly qualified to provide advice on what types of things sex with a woman requires. That said, with ANY partner, there's a learning curve. Often the learning curve is something that YOU have to do partly on your own. You need to know what they need to do. They'll have a hard enough time doing that themselves without having to read your mind. You also have to be ready to listen to what they need, and you have to be ready to follow their instructions.

~ I can't 100% get over the hang up that my first time should be "special". I'm not so sure it's an internal hang up, though - the thing that gives me pause is thinking about how I would explain it to others who ask about it. (This is also the problem with doing this online, so maybe I should just get over worrying what other people think about me.) Is there any way for me to be more sure that this is the right move?

Hmm. I have never had cause to discuss my first time with anyone else. (Wholly unspecial, if you're curious. Met a guy online. Mexican food, movie, fooled around.) That said, you seem concerned about the "how you met" question, to which the answer "online" is becoming more and more standard as time goes by. That doesn't make it for you. But it is becoming less stigmatized as time goes on. (I met my current - and almost all my previous - boyfriends on the webs.) But you need to ask yourself: how many of these stories do you hear from others? I think if we heard these stories, we'd be shocked at how unspecial this whole ordeal typically is. Prom night virginity loss? Roommates fooling around in college? Camp trysts? Online liaisons? Even scented candles and rose petals... It all reads like a bad porno. So whatever you add to that canon can not possibly be worse than what the rest of us have added.
posted by greekphilosophy at 11:44 AM on February 2

I have a lot of trouble with the notion that women "pair" more easily than men, or are more likely to associate emotional attachment with physical attachment.

And to tie that to little bursts of chemicals within our brains?

That conclusion carries the price of human will—even if it places sex as something apart from society's dream of the act.
posted by trotter at 11:44 AM on February 2

~ I can't 100% get over the hang up that my first time should be "special". I'm not so sure it's an internal hang up, though - the thing that gives me pause is thinking about how I would explain it to others who ask about it. (This is also the problem with doing this online, so maybe I should just get over worrying what other people think about me.) Is there any way for me to be more sure that this is the right move?

I think I'll play a little Devil's Advocate with you here. Just reading this part makes me think that you should probably not go through with what you're considering. What you have with your virginity *is* as special as the moment you hope to one day experience. While the grass does seem "greener" right now on the other side, you may feel that the beauty of the experience (that you, in a way, now cherish) becomes cheapened with casual sex. And being only 25, you still have time to find that right guy...or atleast one that will be more of an affectionate BF than a one night stand or casual FWB.

But if you're really serious about this, one question you really need to think about is...how sacred is the act of making love to you? And are you strong enough to emotionally separate love making and casual sex? They are two completely different things despite being a very similar act. Another question is more along the lines of your moral upbringing. If you don't feel now that you could easily carry FWB relationships, you may cause yourself a lot of trouble handling the emotions/regrets you may find yourself trying to supress later on. Can you see yourself in that situation?

Not trying to be a downer on the subject however...with the right attitude and the right types of personalities involved it can be a very enjoyable guilt/jealousy-free experience. It'll just involve quite a bit of a change on your part on how you view the act of sex, and how you view the opposite sex altogether...you seem to be a smart girl however..think it through! But I would also say, trust your heart....if you're looking for that special someone this may work against it.

(oh and like any single guy reading these types of posts..feel free to email. :P)
posted by samsara at 12:04 PM on February 2 [1 favorite has favorites]

I have a lot of trouble with the notion that women "pair" more easily than men, or are more likely to associate emotional attachment with physical attachment.

Well, it's simply a matter of recording what men and women say about their experiences. Women seek out casual sex far less than men (you're free to see this for yourself on Craigslist ... or in this very thread!), and more often wrongly predict how they will feel after such experiences. Women are more likely to experience negative affect when sex is not associated with emotional commitment. There is a good deal of overlap, but the psychological difference is still substantial.

And, seconding greekphilosophy, I don't see how anon's description of f-buds differs from a typical relationship. I don't think your vision will work unless you yourself have more than 1 f-bud (maybe 2 or 3 studs in the stable), because he probably will, and you will probably grow jealous about it. The asymmetry really just invites it. So maybe it isn't a great set-up for someone like you; you may just end up looking and feeling like this girl. The upshot is that you can find a real monogamous relationship that fits your list of needs more easily than you could find the f-bud relationship ... and it will be friendlier to your psyche.

If you are a 25 year old woman and you don't have interested suitors, then you either aren't getting out of the house enough, or are missing the communication signals ... and there are other AskMes on those topics to Google. If you do have suitors, then I would start being more receptive to them, even if they don't seemingly meet all your initial hoped for criteria (extreme pickiness appears to be a common cause of delayed virginity).
posted by dgaicun at 1:39 PM on February 2

Ok, so the first time does NOT have to be special. I actually wanted my first time to not be special - I wanted to make sure I wouldn't stupidly get attached to someone just because they were my 'first.' So that's what I did, and I don't regret it. I slept with a guy I used to casually date earlier that year. We did it a few times, then I realized that I definitely did not like him (in fact, his personality repulsed me a little) and told him I did not want to keep sleeping with him. And I don't regret doing it this way at all. But if most of your life you thought it should be special, then maybe this isn't a good idea for you.

I would say take one of those new friends, and start hanging out with them more and flirting and eventually if you guys do hook up then take things as far as you're comfortable with. If you say you're not experienced at all then maybe you won't even be comfortable sleeping with the first person you start hooking up with. I wouldn't approach them with the proposition of FWB because that could look weird. Just flirt a lot, and hang out alone, invite them over for a movie, etc.

And I wouldn't look online just for guys to sleep with, guys online can be icky. However, if you do want to meet someone to hang out with and date and hook up with, you can try online, although if you say you have new 'friends' who you don't care about messing up friendships with then I'd go for people you know in real life, it's safer. And who knows, you might end up dating one of those guys and liking them - it takes time to like someone sometimes. This is the safer way to do things if you're not sure if this is right for you - this way you don't have to decide right away whether you're gonna sleep with them, because everything will happen one thing at a time, like in most relationships.

Oh, and sex is fun. So don't wait years and years to do it, you'll wish you would've had more time to enjoy it. But don't necessarily jump into it tomorrow just because you decided you should.

And make sure it's someone you can trust at least a little - someone you'd be able to tell to slow down if it hurts, or to stop if you're uncomfortable, and they'd actually listen.
posted by KateHasQuestions at 2:19 PM on February 2

I just want to add that there are many other things to do in bed that are not penis/vagina intercourse that give you a sense of intimacy, accomplishment (yay, I finally did it!), and lots of pleasure, but do not come with the "is he the one" factor.

You say that you haven't done much in the way of fooling around - so start with that! The person you get to second base with probably matters a lot less than the person with whom you first have traditional intercourse. Once you stop focusing on losing your "virginity," you might relax more and just have some fun. You can fool around with whomever you want and not feel like you gave "it" up just for the sake of giving it up.

Just remember that sex means all sorts of things for people, it's not just penis/vagina intercourse. I think we focus way too much on the hetero-normative structure of what it means to lose your virginity, and we build it up into this crazy sacred thing that one must achieve by a certain age. Just throw that out the window, and have some fun. (And please be safe.)
posted by anthropoid at 10:18 AM on February 3

And please feel free to me-mail me if you'd like.
posted by anthropoid at 10:18 AM on February 3