How To Avoid Being A Casual Sex Casualty

July 3, 2010 6:49 AM

Interested in having casual sex, but unable to pull the trigger on propositioning the guy(s) I have in mind. Are my doubts just nerves, or real hang ups? How do I approach these guys? And if you've had casual sex, how did you know it was/wasn't for you?

I'm a mid twenties female whose been sexually active for about two years. I was a pretty late bloomer, lost my virginity at 23. Part of that was a lack of confidence in my own attractiveness, but I also wanted my first time to be really memorable and lovely. Never had any moral hangups about sex. Raised by sex-positive parents, have always had sex-positive friends. I believe as long as both people consent everything is roses.

Anyway, I fell in love two years ago and had a really wonderful time exploring sex with my new partner. Any vestiges of body anxiety were quickly shed. I learned how to get a guy off, how to get myself off better, how to come multiple times. I experimented with some mildly kinky stuff and liked it. I discovered I have a fairly voracious libido.

About four months ago the boy and I parted sadly but amicably. I am finally in a good place but due to logistical factors I can't pursue a serious relationship with anyone, which would be my preference. I will be in the place I'm currently living for a little over a month, though, and it seems reasonable to try and cultivate a safe, exciting fuckbuddy.

Despite being both ridiculously horny and excited by the idea of a friend with benefits, I've found myself hesitant when it comes to actually approaching men about this. There are several people in my town I believe are interested in me, all of whom I'm attracted to on some level. None I'm compatible with enough to date, but I'm not looking to date anyone. Still, I can't bring myself to proposition them, even though I'm pretty sure I'd be successful with at least one of them.

When I'm alone in my room, I think of these guys, groan at myself, and go fetch a vibrator. When I'm actually with them, the idea of being physically with them seems foreign and weird (but not bad) and I don't say anything at all.

So, a couple of questions:

1) Do you think that my hesitance to approach these guys is normal nerves, or is it perhaps a sign that I'm not cut out for casual sex? If you've had casual sex, how did you determine that it was (or wasn't) for you?

2) How should I proposition these guys? Try to be flirty and hope they'll get the picture? Just say, "I would like to fuck you occasionally, how does that sound?" Something in between? (One is an old friend but not a close friend; another is a roommate for the next month; a third is a guy via OKcupid.)

3) As someone who's only had sex in the context of a loving, intimate relationship, is there anything I should know about what casual sex is like?

posted by anonymous to human relations (27 answers total)

First, do NOT flirt with him and assume he'll get the picture. We guys like women who are explicit. If a woman came right out and said she wanted to fuck me casually for a while, I'd be all over that, as would most men. But you have to make sure to spell it all out beforehand. What I mean is, make it perfectly clear that this is just casual sex, that it won't turn into anything. There's nothing worse than being sold a false bill of goods with casual sex. There are plenty of women who think they can do it, but when push comes to shove they want it to turn into a relationship. And changing the terms of the agreement partway through doesn't always work.

So, I'd advise just throwing it out there. Men aren't known for turning down casual sex.
posted by fso at 7:03 AM on July 3, 2010 [3 favorites]

You can't know until you try. If you find that you regret it in the morning, chalk it up as a learning experience and go back to the vibrator. Even if it's a mistake, it shouldn't ruin your life. It probably won't even be the biggest mistake you make all year (and if you believe it could be, casual sex is not for you).

Another thing to keep in mind--only hookers know exactly what to expect from their encounters, because the relationship is defined by contract. When it's just feelings on the line, it inevitably gets more mushy. Hooking up does not guarantee a next time, or even breakfast the next morning. You have to be comfortable with the possibility that you may just never see this guy again. (except for the roommate. The roommate, I would avoid if you're new at this.)

Likewise, you don't need to lay out all the terms beforehand. Just go out for drinks, have a couple, flirt and smile a lot, and kiss him. Believe me, he'll know what's going on. Most guys don't expect (or want) to go from zero to boyfriend in a night--you don't need to define the relationship before you have sex. If it makes sense to drop into the conversation that you're not looking for an exclusive thing, great. Otherwise, wait till the second time you hang out. Stick to drinks and sex, so there's no confusion--don't do datelike things like dinner or movies.

(As an aside: The biggest turnoff I ever had was a guy telling me he wanted to be friends with benefits upfront. I thought any guy who basically kicked me out of bed before I got into it probably wasn't someone I wanted to spend my time with. I didn't want to hook up with a guy whose main concern was to avoid the possibility of an emotional connection--I wanted to hook up with a guy whose main concern was sex.)

Finally, don't freak out if you turn out to actually like the guy. That's not a disaster either. Casual sex is more of an attitude than a relationship. The point is that you want sex, and anything else is bonus. If you can't separate your desire for the bonus from your desire for the sex then stick to the vibrator and your fantasies and have fun.
posted by thinkingwoman at 7:18 AM on July 3, 2010 [1 favorite]

Or maybe guys would prefer an explicit written contract. Shows what I know. Heh.
posted by thinkingwoman at 7:19 AM on July 3, 2010 [1 favorite]

I'd recommend bringing it up after a couple of casual drinks. Why? Because it'll be easier to spell everything out, and as long as he's not completely s***faced, he'll be able to think rationally about it.

Plus, it's much easier to say, 'do you wanna stay at my place tonight?' in that setting.

And pick a casual bar where you can have that conversation - nothing too fancy or that blasts Bad Romance at ear splitting levels.
posted by glaucon at 7:22 AM on July 3, 2010 [1 favorite]

If "just throwing it out there" feels too awkward or forward ("Hello, let us begin having casual sex."), you could always do it the old reliable way. You go out in a casual group situation, you have a few drinks, you flirt hard all night, one of you says let's get out of here, you go home, you get it on, and then you leave the next morning cheerfully and only making vague statements like "well, see ya soon". If he says I love you, give him the double thumbs up and a wink.
posted by Askr at 7:24 AM on July 3, 2010 [5 favorites]

Oh, forgot to say. Do the above then repeat. Just don't start up with the nesting maneuvers and you ought to be able to cruise on through a nice fuckbuddy season. You could throw something in there like "we ought to keep doing this!"
posted by Askr at 7:26 AM on July 3, 2010

There's a vocal snippet in one of the techno songs I listen to regularly; I've no idea what movie it's from, but it pretty much epitomizes what I think you're after. It's a woman's voice, ever so casual and yet with a suggestive lift at the end -- the sort of enunciation you'd get by tilting your head down and looking directly at someone: "... you wanna go waste some time?" I find it sexy as hell, and it says in just a few words what you're after: an encounter, and nothing more. Close the deal with clarification; be explicit. But yeah: generally you'll have to hit a guy over the head with what you want.
posted by seanmpuckett at 7:37 AM on July 3, 2010 [1 favorite]

I had some one-night and one-week stands (never a long and extended friends with benefits arrangement) and found that casual sex doesn't work for me at all. Some people do fine divorcing sex from intimacy and emotion; I do not. And worse, I have tended to find first-time sex fairly awkward and so-so, whereas I've found sex in a relationship to just get better and better as you get to know each other's bodies, increase trust, and be able to take risks. To directly answer your question, I knew it wasn't for me because it didn't make me feel happy and good.

As with all things sexual, different strokes, different folks, and I think the only way you can know is by trying.

On the what to watch out for front, casual sex (particularly the overlapping kind, where you are fucking Bill who is also dating Jane who is seeing both Susan and Fred who...) raises the stakes for safety. "I'll just slip it in for a minute and put the condom on later" isn't such a great idea, but that doesn't stop people from doing it. You can't assume other people will share your values and ideas about safety (whether you enjoy risk or try to avoid it) and it falls totally on you to make sure you are comfortable with what's going on, physically and emotionally.
posted by Forktine at 7:43 AM on July 3, 2010 [3 favorites]

The first part's easy. I cannot think of any straight or bi males in my circles who, if asked sraight up for sex by a woman, would not spend the day in a giddy haze whether or not they actually wanted to play.

The second part's difficult. Your calibration for fun, sympathetic males may not be all you could wish for (for example, a guy who's clean and dresses well is by no means sure to be 'safe' or exciting). Being raised by sex-positive people is a good thing. However, assumptions you make about sexuality might not be valid in the context of other people's behavior and moral strictures, no matter how objectively healthful or generous those assumptions are.

Casual sex made me re-orient my expectations. If you feel like getting off with someone hot and you realize your fantasy is probably going to be better than the reality, then you might get somewhere close to my experience, but the dispersion of situations is very large. You'll get some total fox who has ED or feels pressure and gets angry sometimes, then to make up for it you'll spend a night or two where the fantasy wasn't even half as good as your partner and you spend the next few days thinking how wonderful it is to be alive and strong and healthy and hot.
posted by jet_silver at 8:03 AM on July 3, 2010

1) Sounds like normal nerves to me. Up to a certain age, I liked casual sex (and serious sex when it happened). After that I wanted something else. It wasn't a big revelation, just minor dissatisfaction with things over time. As thinkingwoman says, if you don't like it, chalk it up to experience and don't feel you need to turn it into a big deal. Part of what you want out of this time in your life is to figure out what you like and don't like.

2) If it were me, I'd proposition them for small stuff like coffee, drinks, a bike ride. Where it goes evolves from there. I don't think you need to have a big conversation about it. The norm seems to be that sex is casual sex until proven otherwise. I, also, would not go near the roommate. That could backfire badly.

3) There's a whole range of things you could feel. For me, given my background, it initially had a whiff of shame, guilt, and sluttiness. But after that wore off it was fun, playful, really exciting, sometimes scary, intense. Pick good guys---guys who are good people--not just guys that look sexy. Also, it will range from good to bad sex. Don't overthink the bad sex. Fuck it and move on.
posted by Yoshimi Battles at 8:09 AM on July 3, 2010

I'd say you need to make it clear you're interested in casual sex, or they may assume you want a relationship. Perhaps bring up the subject of friends with benefits in a general way and ask what they think...say you like the idea. Then it may happen naturally especially if you have a couple of drinks. That assumes you want to go for it though. I don't have anything to add about the 'whether' part of the question I'm afraid.
posted by Not Supplied at 8:10 AM on July 3, 2010 [1 favorite]

I think I'm only going to address your third question, about how to handle crushy emotions on someone you're not in a traditional relationship with, because I find flirting waaaaaaaay too easy and don't know how to explain how I get people in bed with me; it'd be like trying to explain how to breathe.

Ok, so I feel like a lot of times dudes who are having casual sex with you want to do what I've dubbed the robot routine. Robots do not have emotions. Robots don't like each other, they don't fall in love, their default state is indifference.

It's kind of a game, and it's usually pretty obviously a charade. If you're seeing someone every couple of days and kissing and rolling around for hours, for example, it's pretty fucking impossible not to develop some sort of feelings for them, even if it's just affection and enjoying being with them, not "I want to be this person's monogamous girlfriend/get married to them/have their babies."

Robot dudes, and dudes who want you to be a robot, are very scared of those feelings. They're so scared of you falling in love with them and wanting to be their girlfriend that they get nervous when you make moon eyes at them while snuggling. For them it's one step from moon eyes to possessive girlcrazy.

There's another form of the robot routine where you actually pretend to actively dislike each other (people look at me like I'm crazy when I say this sometimes, but some of you have got to know what I'm talking about). It's not hatefucking or anything; it's obviously a joke, but it's also a defense mechanism when someone really doesn't want you to fall in love, or even in like, with them.

For example, I remember expressing amazement that I had been spending so much time with a boy and then rolling my eyes and saying "and it's not like we even like each other, or anything." I kissed a tall skinny fixie-riding keebler while we were unlocking our bikes outside the bar and after he pulled back from the kiss he looked me in the eye and said "you bitch." Like, I was a bitch for seducing him into engaging in a kiss, which is something cold soulless emotionless robots don't even enjoy.

I'm not saying every guy is like this, or every relationship is like this (and yes, they're relationships, just not the sort you're used to). But I want you to be prepared for it, so that when a boy kisses you and calls you a bitch, you can shoot back "fuck you, prick" and grab his ass.

Now, not everyone is a robot. I'm seeing a boy right now (and by seeing, I mean pretty much the kind of relationship you're looking for-we're not dating) who expressed amazement when I told him about the robots I'd been with.

"Why would I sleep with someone I didn't even like?" he said. "I mean, there's the sex, but then they're still there afterward, and it's nice if you can actually talk to them. Plus, sex is way more fun when you like the person."

I agree completely. Sex is way more fun when you like the person. I'm not saying you have to love the person, or know them particularly well, or be in an exclusive relationship with them, and I'm not saying there's not a bunch of people who don't give a rat's ass about each other having mind-blowing anonymous sex out there. I'm just saying, it's more fun when you like them.

And to be honest, I liked the robot guys; the "we're too cool for school/affection" shit was all an act. It can be kind of a pain in the ass sometimes making sure you don't betray any emotion at all lest a dude freak out and assume you're about to propose. I much prefer messing around with someone who knows I can't be their girlfriend and knows we're nonexclusive and all that, but is cool with spooning me when I sleep over and texting me dirty things while we're out being cool kids at different parties across town and calling me baby and saying they miss me when they don't see me for a while.

That's just me. I'm not saying you have to be affectionate with a regular fuck buddy; I'm just saying, it's OK to be, and if you find a guy that is not freaked out by it, I would recommend them over some dude who is so commitment-phobic he wants you to pretend to be a soulless fuckbox who hates him.

How to not get TOO attached is a whole 'nother messy novella.
posted by Juliet Banana at 8:18 AM on July 3, 2010 [22 favorites]

It never worked for me; one of us always ended up getting emotionally attached and wanted more. It was usually me.
posted by dzaz at 8:38 AM on July 3, 2010

--------
And if you've had casual sex, how did you know it was/wasn't for you?
--------

I've tried it, and took away the very creepy realization that it basically amounts to pretending to be in love with someone.

I didn't like anything about that, and didn't think I could be good at it (and would be somewhat horrified if I did become good at it). So it ceased to be of interest to me, even though I certainly do feel sexually attracted at times to people I'm not in love with.
posted by Quisp Lover at 9:09 AM on July 3, 2010

1) Do you think that my hesitance to approach these guys is normal nerves, or is it perhaps a sign that I'm not cut out for casual sex? If you've had casual sex, how did you determine that it was (or wasn't) for you?

Sounds like normal nerves, but it's impossible to really say, you know? It's good that recognize the potential minefield casual sex and feelings can turn into, that's healthy and realistic. But it's something you have to experiment with it a bit. Perhaps some heavy make out sessions before going all the way would help you figure out how you feel about it.

2) How should I proposition these guys? Try to be flirty and hope they'll get the picture? Just say, "I would like to fuck you occasionally, how does that sound?" Something in between? (One is an old friend but not a close friend; another is a roommate for the next month; a third is a guy via OKcupid.)

Be straight and up forward. A simple "I'm thinking I might like to try casual sex and you're high on my list to do with this with" suffices to get your unsure thoughts and feelings across.

"Come home with me tonight" also works.

"I want to come over your house, chill a bit, fuck your brains out and then grab a sandwich before leaving" would be a winner.

"Casual sex? Ever heard of it? Want to try it?" makes things pretty clear.

Ask him to imagine you singing a song to him. Send an MP3 of Machine Gun Fellatio's (Let Me Be) Your Dirty Fucking Whore

In short, there's a lot of ways to make this clear to guy. Pick one.


3) As someone who's only had sex in the context of a loving, intimate relationship, is there anything I should know about what casual sex is like?

You may love the person you're being casual with, but you might not be IN love with him, get it? Western society tends to forget that love can have many different permutations in the context of relationships. Expect to become attached in some way and recognize and be comfortable with the fact that such a thing isn't bad.

What you intend and what happens can be two different things. You may fall in love, while he doesn't and vice versa or both of you may fall for each other. Recognize the possibility of that and resolve to not do things that make you or him hurt.

USE PROTECTION.

TALK with the guy about using protection. You don't want any mistakes or understandings.
posted by new brand day at 9:42 AM on July 3, 2010

And if you've had casual sex, how did you know it was/wasn't for you?

I was in the same situation as you (late bloomer, just out of my first relationship) last year. I tried it a few times, but I realized quickly that, for me, sex is just plain not fun with a person you don't care about. Not only is it not fun for me, in fact, but afterwards I found I had no actual interest in the guy- I didn't want more sex, I didn't want drinks, I didn't want to be friends. And I think this was because I never REALLY liked them in the first place. I just knew they liked me and I thought "this could be fun."

Still, I'm glad I had those experiences because now I KNOW I don't like it. Every failed hookup or relationship teaches you something.
posted by showbiz_liz at 9:47 AM on July 3, 2010

I experimented with some mildly kinky stuff and liked it.

Just a thought-- if you really enjoyed the kinky stuff, maybe try finding a place where it's practiced, a mailing list or a meetup, and meet some kinky folk in your local area. Lots of people who do that kind of thing are happy to meet up for some play, with or without hetero sex. It's fun and the possibilities (or not) for realtionships are often spelled out ahead of time.

Otherwise I'd say try the guy from OKCupid; just tell him more or less what you told us: you're fairly fresh from a breakup and you will be moving soon. Fewer possible complications than with the other two.

Good luck!
posted by BibiRose at 10:59 AM on July 3, 2010

1) Do you think that my hesitance to approach these guys is normal nerves, or is it perhaps a sign that I'm not cut out for casual sex?

Normal nerves. After the first one you'll know more.

2) How should I proposition these guys?

Sounds like you could use something of a script, at least till you have more confidence and experience?

IX-NAY ON THE ROOMMATE (at least until you're way more experienced).

Other fellas: Ask them out and get together in the early evening in a casual, quietish setting, one-on-one. Light dinner or coffee or drinks, that sort of thing. Do the flirty touchy things (brush his leg with yours, his arm with your hand, etc.). If he doesn't physically move away, he's probably interested. Ask what his plans are for the rest of the night. He'll probably say he doesn't have any. Touch him and make strong eye contact while asking if he'd like to come over to your place. He'll probably say yes. Say OK, smile, then change the subject. At some point on the way from there to your place, say that you're really looking forward to fooling around with him -- something like You know I'm not looking for a relationship or anything like that, just want to have fun with you. No strings attached, right? and verify that he's okay with that. Once you're at your place, establish any strong boundaries or desires either of you have (e.g., no PIV without a condom, confidentiality, do what you want and I'll say no if I don't like it), then get physically close again and enjoy!

If at any point he says no, don't take it personally. There are definitely guys who are freaked out by being approached by a woman at all, or who have the metacognition to know they want relationships and not casual sex, or who can't go that fast. It's not about you.

3) As someone who's only had sex in the context of a loving, intimate relationship, is there anything I should know about what casual sex is like?

After the first few, you'll learn whether you can compartmentalize or not. Some can and some can't.
posted by brainwane at 11:08 AM on July 3, 2010

I didn't address the emotional aspect of your question earlier, and I want to do so as well as echo what a few other folks have said.

So: fucking is, in general, fun and relaxing and exciting and enjoyable. Fun things, in general -- like fucking and bowling and playing video games and going on walks etc -- are better when shared with friends. And not every friend is the right friend for going on walks with, or going to movies with, or taking to bed. Now there's a tricky bit: fucking can have consequences, like babies and diseases, but also emotional attachment. Intense physical experiences shared with other people tend to create emotional bonds between those people.

Unlike bowling or going on a walk, it's going to be difficult to share orgasms with someone and not become attached to them in one way or another. Conferences are very popular venues for casual hookups because, despite the bonding, participants rarely see each again, and if they do, probably only see each other once a year, so the bond really doesn't deepen much. Making a fuckbuddy out of someone in town means that bond will be strengthened each time you go out (or stay in).

There's nothing wrong with a deep sex-based bond between one or more people, as long as each participant knows exactly what's happening, what's expected of them, and what they want out of the relationship. So communication is key. But not just communication with your partner; communication with yourself. Monitoring your own desires is just as important as being in touch with your partner. There's a reason successfully polyamorous (which is a step beyond what you're asking about, I know) people spend a whole hell of a lot of time talking to each other as well as introspecting -- because open air communication is absolutely essential to keeping needs, desires and expectations in tune.

Here's the neat thing, though: once you understand the importance of open communication -- "here's what I want, here's what I'm willing to give" -- exercising that communication with your cadre of friends (not just fuckbuddies, but all of your friends) means you will have some folks you like to dance with, some folks you like to go out for coffee with, some folks you hit the art galleries with, and some folks you like to writhe around with like greased weasels, and some folks who are good for multiple things. (And if you perchance find a person or persons who are into multiple things you're into, maybe you do let the bond deepen to romance.)

So: say your piece, listen to theirs, talk it out, come to an understanding, and if everything is copacetic, then hit the sack. And then keep talking, because feelings keep changing.

Hope this helps.
posted by seanmpuckett at 11:31 AM on July 3, 2010 [1 favorite]

The key to making it non-relationship is to keep it simple. So three questions in order should do it.

"Wanna go out for drinks?"
"Wanna come to my place?"
"Wanna fuck?"

And if the answer to any question is "No", no big deal. You shrug and smile and move on, you happy-go-lucky person, you.

That is, keep it all casual.
posted by rokusan at 11:39 AM on July 3, 2010

Well just to add my two cents ... not every guy out there is into casual sex.

I'm not saying any of the guys you're interested in won't be interested, I'm just saying that not all men are cut from the same piece of cloth. I'm not, and that's probably one of the contributing factors to the mess I am, but, to me, it sounds like it's partially nerves on your part.

You sound like you've got a good head on your shoulders, and you're not going into all this without any undue expectations, so I bet you'll be fine.
posted by Relay at 12:35 PM on July 3, 2010

1) The "wow this is weird" feeling is, in my experience, a bad sign that the sexual thing you're about to do is going to be unpleasant or uncomfortable. That doesn't mean you can never have casual sex. Maybe you're just not ready right now or the chemistry isn't clicking. Willingness/desire to have casual sex varies even for people who like it.

1) a. Depends on your definition. Sex without a commitment, without monogamy, without a well-defined dating relationship? Yes, I am motivated to do it and I enjoy it. I discovered this because I wanted to do it, I tried it, and it was fun.

Sex without emotional intensity? I don't like it and if I can't go there with someone, I don't want to interact with them sexually. For me there is an intense mental and emotional component to sex that makes it...well...sexy. One-night stands or sex with strangers--not something I seek out because I wouldn't feel comfortable having that level of intensity with someone I didn't know at least a little bit. (Part of this is that I really enjoy power exchange so your vanilla mileage may vary)


2. I suggest being honest about what you want and what your concerns are. Say "man, I'm really horny, and I kinda want to make out with you, but part of me thinks it would be really weird, and I've never done a casual thing before. What do you think?"

No, it's not the world's most irresistible, sultry, confident come-on. It's honest and you won't have to fake anything you don't feel, and that's important when you're already feeling strange and uncomfortable.

3. You don't have the right to lie or be an asshole. You DO have the right to:

--feel how you feel, even if that's "I'm in love with him!!!" or nothing at all
--be irrational
--end the sex or the relationship at any time for any reason
--ask for what you want, even if it's irrational or weird or whatever
--enjoy yourself
--only do things that are fun
--have emotions
--get attached

Some things to remember about emotions:
--you can have emotions without acting on them.
--unpleasant emotions don't have to be anyone's fault. Sometimes they just happen.


Best of luck!
posted by internet fraud detective squad, station number 9 at 12:36 PM on July 3, 2010 [5 favorites]

Could me among those guys who have plenty of times turned the prospect of casual sex. I prefer to have on-going (even if they're casual things). I've been hurt plenty when I thought the situation was going to be on-going, but instead the person never calls. Explicit is better, if you want people to actually consent.

I also agree that it can be much hotter in theory than reality. Be honest abut what you want, and your nervousness. Anyone who reacts greedily, or badly, is maybe not a good match :)
posted by gregglind at 12:58 PM on July 3, 2010

Take it from someone who knows: casual sex with a roommate rarely, if ever, ends well. If you're going to go this route, do yourself a favor and skip person #2.
posted by perpetual lurker at 1:54 PM on July 3, 2010

As a male, I agree with the first commenter. We men are often not at all adept at picking up the clues women are broadcasting. (Presumably, women know this.) So, show some interest, flirt, and then just grab the guy's hand and make your pitch.

Beware, though, that emotional attachment can creep up on anyone, including you. Or the guy. Do you know what you will do if you don't want it to be so casual anymore and he does? Or vice versa? Few of us can remain indifferent about someone we have sex with on a regular basis.

And tell the guy you want to keep it casual before you sleep with him for the first time, not after.
posted by justcorbly at 3:30 PM on July 3, 2010

I think that the Brits have this one nailed: "Fancy a shag?" It can go either way, and everyone's still an adult afterwards.
posted by jimfl at 6:06 PM on July 3, 2010 [1 favorite]

Well you could try that in Britain jimfl, but good luck with that!
posted by Not Supplied at 12:38 PM on July 7, 2010