How do I have an honest, ethical fling with a friend-of-a-friend?
May 13, 2014 10:11 AM   Subscribe

I have never had a legitimate fling before. Lately I've been showing a lot more potential for it. I was kind of a late bloomer- I skipped the crazy college years because I was engaged to one guy during all of that (and was also a very different, more prudish and sheltered person at the time)- and then I moved around a lot and worked a lot and only dated a few other people. I don’t know what I’m doing. This is all new to me. I’ve made out with random guys in bars a couple of times and flirted with the idea, but that’s as far as it’s gone. Stranger sex has never really appealed to me- I always thought that a friend-of-a-friend would be perfect for a fling. But maybe not if it’s too close to home. So, how do I do this? Is there a way to have an ethical and honest fling and not hurt anyone’s feelings and still be friends with my friends?

Hi again MeFi. You might remember me from my previous question regarding confusing dating situations, okcupid, and friends-of-friends. Jesus Christ I am sorry, but I have to come back for more advice. If you don’t want to read all of that (it's only tangentially relevant anyway) the basic strokes are that I am a single 26 year old woman who moved back to my hometown and made a bunch of new friends. Most recently I made friends with a group of guys in town who kind of all know each other. Well, worse than that, the “core” four are long-term friends since college and have a band together. Instead of following amaire’s brilliant advice to take things slowly and not kiss one of them, I…kissed one of them. The first day (night) I met him. It was…not one of my more proprietary moments.

This was last Thursday. He invited me back to his place that night and I was really tempted but said no because it was my girlfriend’s (let’s call her Alice) 27th birthday that weekend and this guy (let’s call him Dan) is long-term friends with her brother who was in town celebrating with us. After making out with this dude, I had a massive guilt attack and then we awkwardly made our way back to the rest of the group and then my other friend (let’s call her Betty) rescued me and I went home with her and slept on her floor rather than going back with them or driving home. The next morning I kind of freaked out and texted Alice about hos before bros.

So Friday I went out with them again determined to pretend nothing happened. I decided I was never going to think of it again and put it behind me. It’s just kissing after all, right? Kissing is totally forgivable and stupid. We were drunk, I figured it would be easy to “forget to remember” it forever. Yeah, guess what, that didn’t happen. I go out with Alice and her brother and his other friend, purposefully avoiding carpooling with Dan. But Dan shows up later and flirts with me all night while I studiously avoid eye contact. At some point we’re chilling and he offers to get us food and then he needs someone to go with him and of course, a bunch of people basically conspire that it should be me. I go with him, knowing this is not going to end well. It totally doesn’t. I tell him, “hey dude, you’re a fantastic kisser, but hos before bros.” His response to that is to grab me and make out with me some more. I…..well….I let him. He really is a fantastic kisser. The whole group goes back to his place and I crash on Dan’s air mattress with Alice. She cock-blocks any attempt he might make to sleep with me that night, and the next morning I have to get up early for work.

Later on I found out Alice had a little come to Jesus talk with him while I was at work about not inviting me home when I was drunk and also not treating me like a ONS because she likes me and wants to “integrate me more into the friend group” and “doesn’t ever want to be forced to pick sides.” This guy is really not a total ass, I promise. He backed off a lot that day. Everyone is hung over except Alice and I, we get a moment alone and have girl time. I tell her I do not know if I want to sleep with him or not but I’ll decide soon. She says that it’s up to me and basically that she doesn't want things to be weird, but she won't be upset if I go through with it. (She's had a fling before and thinks I need to live a little bit as an older friend, I think.)

I am pretty damn sure I want to have a fling with this dude. He is a really, really good kisser! But I really like my friend and don't want to make things awkward for her or me forever. Even worse than that, two of the other guys totally also were kind of flirting with me. One of them lives with the guy I made out with. The other one just sent me a message on Facebook inviting me out for drinks. I seriously can’t date three guys who all know each other at once. But fling guy is just fling guy- he’s hot and a year younger and a good kisser. That’s it. Other two guys are more relationship type guys. I don't know if I want a serious relationship right now anyway. I want to live a little! I want to actually be young and do whatever the hell I want for a change. I'm tired of neediness and cuddling and nice guys and anniversaries and that whole scene. I am super busy at work and with family obligations and don't really have time to be a "girlfriend" anyway. But....well, I like sex.

He asks me out for dinner to talk about things Sunday night after everyone else went home. I tell him I talked to Alice and its okay with her. (I am not really sure if it’s 100% okay in her heart, but she did say it was okay.) I also tell him if we’re gonna do this, it’s completely a fling. He is on the same page. He tells me he hasn’t had sex in a long time and has also never had a fling but he's completely okay with it and doesn't think he'll get attached. We attempt to establish some ground rules. Rule 1: We don't hang out together alone. Rule 2: We tell each other when we date other people. Rule 3: We have to stay friends.

I end up telling him I'm pretty busy this week. I talk to Alice again, she suggests that we also establish a rule for how long this goes on.

I mean, if fling guy ends up marrying my friend (unlikely) or I sleep with one of them and then marry another one of them (slightly more likely but still pretty unlikely) things are going to be really fucking awkward at the wedding, let’s put it that way.

Is this the worst idea anyone has ever had in the history of ever? Or not? Am I showing serious Yoko Ono potential here?

TL; DR I made out with my friend’s brother’s friend on her birthday weekend; now I want to have a fling with him, help me not ruin everyone’s lives simultaneously.
posted by quincunx to Human Relations (56 answers total) 6 users marked this as a favorite
You need to muster up a deeper sense of maturity if you want anything to work. You're coming at all of this with the foresight of a teenage girl educated by Cosmo magazine.

Just take a huge step back, realize you're an intelligent adult women, and that life isn't like a sitcom. From that point make confident and assured decisions, with the willingness to take responsibility of things go sour. Most of all, remain poised and stoic, but also don't deprive yourself of the joys of life because you think your friend might marry a friend of a friend in ten years time and the wedding would be awkward.
posted by jjmoney at 10:23 AM on May 13 [27 favorites]

I made out with my friend’s brother’s friend on her birthday weekend; now I want to have a fling with him, help me not ruin everyone’s lives simultaneously.

Just don't be ass about whatever happens, but realize that there's nothing you can do about his behavior. All you can do is control yourself.

Rule 1: We don't hang out together alone.

Unless you have a very interesting social circle, presumably you two will be having sex when you're alone, so that breaks Rule 1. You may not be consider having sex hanging out, but unless you two intend to have sex in bathrooms at restaurants, you'll be hanging out a little before and after the sex.

Rule 2: We tell each other when we date other people.
Rule 3: We have to stay friends.

These sound like good rules, but once you're in it, either or both you might feel different. You can make all the rules you want, but once emotions get mixed in, rules can go out the window. Proceed with eyes wide open, knowing that you will not have full control of the situation, because you can't control another person or their feelings.

Don't over think this and don't be ass. Have the fling, have fun, move on and act like an adult when it ends, even if you don't want to.
posted by Brandon Blatcher at 10:35 AM on May 13 [1 favorite]

Have a fling. Stop asking other people's permission to have flings, you're an autonomous adult who gets to choose who she sleeps with. It might work out, it might not. There's no way to tell, and you can't live your life not doing things in case they go wrong.
posted by Joh at 10:37 AM on May 13 [9 favorites]

"hey dude, you're a fantastic kisser, but hos before bros."

many fine gentlemen would have found this extremely offensive.

you are creating a reputation for yourself. guys will take advantage of this and treat you like a disposable piece of tail.

alice is presuming to set rules for you and fling guy? adults make their own rules for relationships. are you an adult or not?

yoko ono started out with a constituency of one, and did a good job in what must have been a difficult assignment. who's your constituency?
posted by bruce at 10:40 AM on May 13 [6 favorites]

I can't even work out what you think the problem here is. Why would Alice or her brother have any input into the nature of your relationship with this dude at all? You say "hos before bros" a bunch of times, but what do you mean by that? That she gets veto power over your love life?

If you were actually hooking up with her brother or it's a guy she has a long and sordid history with, that might be one thing, but this kinda looks like a lot of manufactured and unnecessary drama to me.
posted by Andrhia at 10:41 AM on May 13 [27 favorites]

Part of what you're doing here is, I think, just coming to AskMe to get the permission to have this fling that you are for some reason refusing to grant to yourself. You're making up bullshit, flimsy reasons not to sleep with this guy because you're scared of the unknown. It doesn't matter if I give you permission if you won't give yourself permission, but here: I give you permission. Go sleep with the good kisser.

The other thing you're doing here is overestimating your importance in other peoples' lives. These are people, not porcelain dolls. I mean, don't take that as an excuse to trample their feelings thoughtlessly, but you know, if you end up hurting some guy's feelings, he'll survive, I promise. And if you have to sit through an awkward wedding or party where a guy you slept with and then broke it off with is also there, you'll both survive that too.

Look: If you decide you want to have a fling, and are honest with everybody and mature about your behavior, you should not cause any problems. This is not to say no problems will occur, but if they do, it will be because other people were not equally honest and mature. That's on them, not on you. Worst case scenario: you fuck up. Your friends either forgive you for it, because they're good friends, in which case, great. Or they don't forgive you, because they're shitty friends, in which case, hell with them.

My advice? Don't establish so many "rules", don't worry so much about what everyone else thinks about you, and don't spend so much time imagining convoluted soap-opera plot lines for how it'll end up ruining everyone's lives. Be honest, treat people decently, and go have some fun. Anything that happens after that is just, y'know, life.
posted by mstokes650 at 10:42 AM on May 13 [11 favorites]

Not the worst idea in history. Casual sex with friends can be a wonderful thing when you're a single person and want sex with someone who isn't quite a stranger, but to whom you feel -some- connection.

The key, IMHO, is to make sure -everyone- is on the same page and that expectations (of the relationship) are aired frequently. You guys have started down that route, so that's good, but you need to consider some other things. You're getting very hyped up (in your head) about this fling and this guy - What happens if you DO have a fling with this guy and he's a disappointment? What happens if you develop attachment to him? What if he develops attachment to you?

As long as you're aware of these things, and have a vague idea of how to handle these situations should they occur, I think you should go for it. Having a fling with a friend can be a lot of fun. :)
posted by stubbehtail at 10:43 AM on May 13 [1 favorite]

I mean, if fling guy ends up marrying my friend (unlikely) or I sleep with one of them and then marry another one of them (slightly more likely but still pretty unlikely) things are going to be really fucking awkward at the wedding, let’s put it that way.

Wait, is Alice dating this dude? Otherwise he's fair game.

You are really beanplating this. That makes me think there's something else you're not facing, likely fears of rejection and/or romantic hurt. Acknowledge those fears and try kissing him one more time. There are no decisions that must be made right now. Explore without demanding of yourself that it all be worked out ahead of time.
posted by Ironmouth at 10:43 AM on May 13 [3 favorites]

I think you need to internalize that you are the captain of your own ship and in charge of your own life, but also that with some exceptions, how you run your life isn't as important to other people as you seem to think it is because most people are too busy living their own lives.

So, unless there's some kind of history between Alice and Dan, I don't see why it would bother Alice if you dated or hooked up with Dan. The "hos before bros" thing is usually applied when you're talking about something like a friend's ex, not a friend of a friend.

The only potential pitfall I see here is that if some point in the future you are interested in dating one of Dan's friends, that might not work if they follow a "bros before hos" (ugh) code. But that's just a hypothetical at this point anyway.
posted by Asparagus at 10:46 AM on May 13 [2 favorites]

There's some pretty deep irony in casually referring to your girlfriends as whores, while obsessively worrying about being seen that way.

My advice would be to fuck whomever you want, and get a new, less degrading catchphrase. Both are the choices adults make.
posted by mkultra at 10:47 AM on May 13 [8 favorites]

You seem so hung up on what Alice thinks that part of me is wondering if it's Alice that you really want to sleep with. If that's the case, ask her, but be prepared for her to say no. If that's not the case, then just fuck the guy already if you want to.

Usually the cliche'd advice is for people to not think with their junk; in your case, I think that's exactly what you do need to do. Set aside what your logical brain is telling you that you should or shouldn't be doing, and ask yourself - "does this guy make my panties wet, yes or no". If yes, go forth and boink. If no, find a guy who does and go forth and boink him.
posted by EmpressCallipygos at 10:48 AM on May 13 [2 favorites]

Okay, I didn't literally say, "Hos before bros" to him, guys. That was shorthand for a conversation I had with him in which I basically said, "this weekend is supposed to be about my friend and I don't want to make things awkward for her." But they DO have a long history- I'm the interloper here. And she used to kind of like him, years ago, and they've flirted a bit before. They know each other's families and grew up together type stuff.

Also, the judgment is helping here- it's making me realize that people ARE definitely going to judge me for this, for whatever reason. (Whore, young, selfish, whatever) So...thanks, actually.
posted by quincunx at 10:48 AM on May 13

What? No. Just sleep with whomever, but if you do it with a guy you have mutual friends with, prepare to see him forever and ever. I don't really get this at all.
posted by the young rope-rider at 10:55 AM on May 13 [8 favorites]

Most of the people you will meet in your life will be friends of friends because that is how people socialize. This is not an outlier situation. Do your thing.
posted by fingersandtoes at 10:57 AM on May 13 [9 favorites]

Also, the judgment is helping here- it's making me realize that people ARE definitely going to judge me for this, for whatever reason.

You're not wrong! Now all you need to do is realize how completely irrelevant those judgements actually are. Because being judged by people IRL really isn't going to impact you much more than being judged by random drive-by internet commentators does. So: "People will judge me!" Yeah, they will judge you no matter you do, whether you sleep with this guy, or don't sleep with this guy, or can't make up your mind and spend days and weeks agonizing over it - in any of those scenarios, people will judge you. So what? Doesn't matter at all. All that is, is another flimsy excuse you're inventing to convince yourself you mustn't sleep with the guy.
posted by mstokes650 at 11:01 AM on May 13 [2 favorites]

Sorry this is so stressful, but I wholeheartedly encourage you to go at this dude and break yourself off a piece

Get it get it
posted by Greg Nog at 11:07 AM on May 13 [17 favorites]

I think the fact you think people in the comments are judging you for wanting to sleep with the guy is very telling.

Most of the comments to my eye read in summary as you can act like a grown up and sleep with who ever you like, there is nothing wrong with it, there may be consequences but adults deal with them it's no big deal.

I wonder if the only person really judging you here is you. It's OK not to sleep with people if you don't really want to. It's OK to sleep with people if you really want to. It's OK to flirt a little and kiss a little and enjoy that and still not sleep with someone. It's not OK to assume you can control every single aspect of what might potentially happen 10 years down the track that way lays madness. What makes, flings and heck even relationships so exciting is the unknown. You don't have to take the chance if you don't want to, but it's OK if you do.
posted by wwax at 11:08 AM on May 13 [11 favorites]

it is unclear whether you have nailed sunday night down as a one-on-one dinner with dan, you seem to be sending mixed signals to him and he may be confused, i know i am. if you get him alone where alice won't be able to cockblock him like she did before, by all means, fuck his brains out, you know you want to, and a great many young people do this every once in awhile, and there isn't anything wrong with it, as long as you take precautions to avoid pregnancy.

the problem is the drama you have built around this, your need to consult alice, your need to consult strangers on the internet to feed into your self-image as the queen of a dysfunctional and debauched court. you're the star here and i'm just a supernumerary, a spear-carrier who lacks the authority to veto your libido, so i say, go for it.
posted by bruce at 11:10 AM on May 13 [1 favorite]

I want to have a fling with him, help me not ruin everyone’s lives simultaneously.

I realize you're exaggerating to be cute, and it's very cute. I am charmed. At the same time, it might actually help you worry less if you don't phrase things in exaggerated terms, even in your own mind. I'm sure you already know that no one's life is going to be ruined if you have a fling. If you phrase your concerns more precisely, you might find doing so narrows the field of anxiety proportionately.

Am I showing serious Yoko Ono potential here?

I think there is some seriously harsh and ongoing judgment of her involved in using her name as a shorthand for a woman whose marriage to one guy allegedly broke up a group of guys, decades ago.

Yoko Ono is cool. She is an artist in her own right. You could do a lot worse than to be her.

hos before bros

My friends and I came up with "girlies before burlies." It makes us laugh.
posted by Bentobox Humperdinck at 11:21 AM on May 13 [17 favorites]

You seem really intent on making this into a bunch of drama regardless of the actual situation or what people says. Who cares what your friend thinks or whether or not you might see them at some hypothetical wedding? If most adults got pissed or judgey every time someone in their social circle hooked up, they wouldn't have any friends. You say you want to have a fling with a friend of a friend because that's ideal, but clearly for you it's not. Maybe you should do online dating instead if this is going to cause you this much anxiety over "being judged". Then you can see people that have no connections to your current social circle.

It sounds like your obsession with being judged as a "whore" or Yoko Ono or whatever is coming more from yourself than your friend.
posted by bradbane at 11:23 AM on May 13 [5 favorites]

This happens all the time, dude. This is how people hook up.
It was considerate of you to ask your friend before hooking up with her bro's friend. And now she's given you her blessing. It seems like she was "cockblocking" him out of concern for you, since you were already drunk, rather than because she thinks it's super bad for you to have a fling with that guy. If you want it, go for it.
posted by winterportage at 11:26 AM on May 13 [1 favorite]

If you feel like you, or your group of friends, are going to react to a break-up or dating and/or hook-up activities negatively and it'll affect your friendship, then it may as well be a self-fulfilling prophecy.

People hook up, date, get married, get divorced, and do so at varied levels of engagement and responsibility. Some people have trouble dealing with _anyone_ they've ever dated but no longer do. Others have great friends that happen to be exes. If you're afraid of your own reaction or the reaction of some guy to the fact that some day you may have a history that ended in a less-than-optimal way, then date outside your social group.
posted by mikeh at 11:30 AM on May 13 [1 favorite]

Also, the judgment is helping here- it's making me realize that people ARE definitely going to judge me for this, for whatever reason. (Whore, young, selfish, whatever) So...thanks, actually.

What?? Your interpretation of posts here are radically different than mine. I see a lot of answers saying essentially, "go for it, there is nothing wrong with what you want to do, there is no reason for people to judge you, this is normal behavior, stop overthinking it and worrying about what other people think of you, go ahead and enjoy".

Your takeaway seems to be that we (or lots of other people) will judge you negatively. This is not the case. 99% of people will not care. Maybe 1%of people will judge you negatively, but they are dicks and you shouldn't care what they think.
posted by Joh at 11:30 AM on May 13 [4 favorites]

I also used to be very sheltered and prudish. Doing things like kissing boys I wasn't in love with and having flings were unthinkable when I was younger, so I started having a bit of guilt later when I did these things in my mid-late 20s. I over-analyzed it all. I worried about what people would think of me, and how I would be changed. This is okay. This is how I learned about myself, and how I grew to be a different person.

And now, in my 30s, I do not regret any of that at all. Not even a smidge, not even when maybe it wasn't the best idea. I like to think of all of these things I did sometimes. They have made my life more interesting to me.

So, I think it's okay you are worried and maybe over-thinking this, and concerned about everyone involved. But, I think it's also important to fully accept that it is okay to do things you really want to, even if there is a little old voice in the back of your mind telling you it is not okay.
posted by umwhat at 11:31 AM on May 13 [4 favorites]

How to have an ethical and honest fling: only have flings with available people who are consenting adults who consent. Communicate about your wants, desires, etc and be up-front with your intentions. If emotions develop that aren't reciprocated, break up.

You can, actually, date multiple people simultaneously - a lot of people do and just keep it on the up-and-up. This is why it's a relationship milestone to have "the talk" to turn dating into a committed relationship.

So Alice and this guy grew up together and have a history. They're not dating now and sounds like they're both available, so there's a reason they're not together (i.e. he's available). It's a good policy to take people at their word, like the multiple times Alice said it was okay to date him.
posted by bookdragoness at 11:32 AM on May 13 [2 favorites]

Also a friend's brother's friend is like the definition of fair game. I mean if this guy were any further removed from you he would be a total stranger.
posted by bradbane at 11:32 AM on May 13 [8 favorites]

I mean, if fling guy ends up marrying my friend (unlikely) or I sleep with one of them and then marry another one of them (slightly more likely but still pretty unlikely) things are going to be really fucking awkward at the wedding, let’s put it that way.

Is this the worst idea anyone has ever had in the history of ever? Or not? Am I showing serious Yoko Ono potential here?

Respectfully, I think you're blowing this whole thing way out of proportion. Nothing that you've written gives me any indication that anything bad will happen if you start hooking up with one guy that you are new friends with. If you start hooking up with this guy, what will probably happen is that you guys will have sex a certain number of times, until one or both of you decide to call it off. At that point, you'll have to decide whether you want to maintain the friendship. You're not going to make any hypothetical wedding awkward. You're not going to be the reason a band breaks up. You're going to have sex with a guy, and most people's reaction is going to be along the lines of "Oh, ok, I didn't know that" when they learn the news.

This is not as big a deal as you are making it out to be. Go do it if you want to do it.
posted by 23skidoo at 11:32 AM on May 13

For what it's worth, what I get from your post and responses is that you would judge yourself, or the possible fling, too harshly. If you both have something that seems casual and he breaks it off, will you be cool him being in a larger group of friends you're hanging out with in the future? What about vice versa?
posted by mikeh at 11:38 AM on May 13

This "fling" sure has a lot of ground rules.

I understand the importance of being open and honest, good communication is important, but all this back and forth and talking over dinner and permission from Alice that maybe likes him but maybe doesn't and fretting about how it will affect all of your future relationships and whatever else might be running around in circles in your head is way too much. Flings have risks, sure, but the overall experience should be fun.

And I'm a little older than you and "Dan," but if a woman told me over dinner she got permission from her friend to sleep with me I would be a little put off.

So, I'll say maybe hold off on sleeping with him. Not because I think it will be terrible for all future relationships (sexual & platonic) or that you're a bad person because maybe Alice likes him or maybe you like his roommate more. It all just sounds a little emotionally intense and nothing has really happened yet. If the idea of sleeping with him has sent you into a tailspin, actually doing it might be a little too much right now.
posted by AtoBtoA at 11:44 AM on May 13 [6 favorites]

Bentobox Humperdinck: "hos before bros

My friends and I came up with "girlies before burlies."

"Chicks before Dicks" is a common one I hear (I'm a dude FWIW)
posted by I am the Walrus at 11:52 AM on May 13 [1 favorite]

No lesbian in the history of lesbians would ever get laid if it weren't for flings/relationships with friends and friends-of-friends and exes-of-friends and exes-of-exes.

You are also overthinking this more than 10 lesbians put together, which is a lot of overthinking, because we are champions of that.

Go. Have a fling. Acknowledge that it may (will) not go exactly to plan because you're both people and that's how we roll, but don't try to control or anticipate every little thing about it, because you can't (again, because people). Have fun and be safe.
posted by rtha at 11:57 AM on May 13 [7 favorites]

Yeah, some excellent points. First thing: Yes, I am mostly exaggerating with the marriage thing. Maybe that wasn't obviously jokey enough, but actually what I am worried about is more like: losing friends, becoming a bad person I don't recognize, making this dude attached or getting attached myself (slightly less worried about me, but I realize guys have feelings unlike the stereotype) making my friend feel jealous or bad, etc.

I think maybe I am just not cut out for this kind of thing. I don't have enough experience to not mess it up. Strangers have no appeal, but friends don't either! There's not really a happy medium.
posted by quincunx at 12:07 PM on May 13

I don't have enough experience to not mess it up.

You might! We all might! That's how we gain experience! No one is born cut out for this kind of thing, and most of us spent huge swathes of our 20s doing things badly, from which we then accrued tiny tiny amounts of wisdom. Which helped us later!

This is new and weird and scary! That's good! Jump on into this fire like a Targaryen on a camping trip, lady!
posted by Greg Nog at 12:15 PM on May 13 [8 favorites]

The way to get experience is to try.

Tell him you're new to this kind of thing. Tell him about your concerns about his feelings and yours.

Stop letting Alice set the ground rules. Stop trying to safeguard her.
posted by RainyJay at 12:15 PM on May 13 [2 favorites]

bruce touched on a point on which I would like to further elaborate.

If I'm reading this correctly, you came on pretty strong the first night you met this guy (Thursday). The next night you walk off with him despite "knowing it won't end well", make some apparently half-hearted comments designed to wave him off but end up making out with him. Again. By Sunday you've let him know you're interested in a fling.

(By the way, I'm not suggesting there's anything wrong with this.)

This guy is best friends with three other guys, two of whom are also openly flirting with you and inviting you out. I find that a interesting since there's little doubt these guys know their friend is pursuing you, especially the roommate who also asked you out. I'd like to point out that there's a very real possibility that, as bruce says, you're creating quite a reputation for yourself.

I can't stress strongly enough that I see nothing wrong with dating and/or sleeping with multiple people whenever it suits. I'm just concerned that these guys, either individually or collectively, see you as an easy lay. Again, that's nothing to be ashamed of or judged for but if you're worried about being judged in the first place, well...
posted by _Mona_ at 12:16 PM on May 13 [1 favorite]

You're never going to get the experience without getting the experience. All of the things on your list (except the turning into a bad person one) are things that are really at least as up to other people as to you.

Like, if you are upfront and not a jerk, and you do your best to be kind, and a friendship gets messed up anyway - how is that a thing that was solely at your doing? It wasn't! It would also be on the friend for not communicating honestly etc.

I guess if you're really not feeling it for this circumstance, then fine, but some of the way you've talked through your thinking out loud here makes me think you're not doing yourself any favors for future-you.
posted by rtha at 12:19 PM on May 13 [2 favorites]

becoming a bad person I don't recognize

I honestly have no idea where you're getting this. Is he married/attached monogamously or developmentally disabled? No? Then what? This is really heading towards therapy territory.
posted by the young rope-rider at 12:19 PM on May 13 [7 favorites]

I think it's telling that you were interpreting everyone's reaction that you were thinking way too much about this as "judgement". It's not judgement, it's more asking "where are YOUR feelings in all of this?"

Maybe that wasn't obviously jokey enough, but actually what I am worried about is more like: losing friends, becoming a bad person I don't recognize, making this dude attached or getting attached myself (slightly less worried about me, but I realize guys have feelings unlike the stereotype) making my friend feel jealous or bad, etc.

The points you mention above are all good ones, and important ones. What we're saying is, is that it looks like you are valuing the feelings of everyone else in this situation EXCEPT your own. It's great that you want to be sure that you don't break up the band or anything, but it reads like you are completely ignoring what YOU want. Maybe that's what the problem is - it looks like you've spent so much time figuring out how not to shake up your circle of friends, you haven't spent enough time figuring out what you want specifically. It's good to be conscientious, but - include your own self in the group of people you're trying to satisfy.

I think maybe I am just not cut out for this kind of thing. I don't have enough experience to not mess it up.

Well, maybe - it depends on what you mean by "this kind of thing". Do you mean sex at all? Sex with people who are part of your friend group specifically? Flings vs. serious relationships?

There is no wrong answer to that question, by the way. Knowing what it is you actually want is a REALLY important step towards being able to navigate your social life - because if you don't even know what you want, you aren't going to be able to negotiate FOR it. And being able to negotiate for it amongst your friends IS the way you'll be able to pull this kind of thing off without breaking up your social circle.
posted by EmpressCallipygos at 12:19 PM on May 13 [1 favorite]

Okay, I have a different perspective on this. I never went through a casual sex phase and have yet to regret it. I am a sensitive person--you seem like you might also be from the way you describe your anxiety--and I prefer not to sleep with people until I know that they are good people who will be nice to me.

There is NOTHING wrong with sleeping with someone you don't know well. There is NOTHING wrong with flirting, hooking up, or being casual, as long as you communicate that that is what you want. But those things are not for everyone, and they don't have to be for you. If having this fling is just going to make you anxious, the sex may not be worth it.
posted by chaiminda at 12:28 PM on May 13 [3 favorites]

actually what I am worried about is more like:... becoming a bad person I don't recognize...or getting attached myself

For these worries, I suggest examining the thoughts and feelings that were happening during these ellipses:

Ikissed one of them. The first day (night) I met him.

His response to that is to grab me and make out with me some more. I…..well….I let him.

It's not entirely clear how much agency you had in those key moments, or could have had if you had chosen to claim it. If you're shrinking back and letting him drive, letting others conspire to put you two alone together, letting others cockblock if they think necessary, letting Alice tell you whether it's OK, then I can see how that would contribute to anxiety about the situation. You are not making the decision about this fling; everyone else is.

What I would do is not tell anyone in the friend group anything more about the fling. Not as in, hush hush it must be kept secret due to shame and judgment. Just as in, drawing a bit more of a boundary around what is your decision, the private choices of you and this guy. I'm sure people will find out. They always do. They already suspect. But if they ask, I would give them drama-reducing answers like, "oh there's nothing to tell" and changing the subject. Just make sure you keep good, open communication with the dude himself and make sure everything continues to be square between the two of you.
posted by Bentobox Humperdinck at 12:44 PM on May 13 [3 favorites]

The people who are getting up in OP's face for seeing judgment where there is none must have missed this gem, from bruce:

You are creating a reputation for yourself. guys will take advantage of this and treat you like a disposable piece of tail.

and this slightly less egregious but still frustrating follow-up from _mona_:

I'd like to point out that there's a very real possibility that, as bruce says, you're creating quite a reputation for yourself... I'm just concerned that these guys, either individually or collectively, see you as an easy lay...

This is pure judgment dressed up as altruistic concern: "Oh, it's not that I think you're acting slutty, I'm just worried for your sake that those bad men might," and it's a classic way of policing sexual behavior.

For my part, I would be skeptical of the risk of getting judged as "an easy lay," just because you've only kissed one guy and are considering the possibility of sleeping with him. Depending on where you live, and the kind of circles you run in, I think you'd have to sleep with at least two of the band members before you started acquiring anything remotely resembling a "reputation." Lots of times when a new lady enters a social circle there's a buzz of excitement around her for a while; it doesn't mean she's doing anything wrong, and even if she bones every guy in the group, it's still on them if if they decide to treat her as "disposable." (gross.)

That said, I do agree with the person who said that running the risk of other people's shitty judgment is a consequence of being a woman who has sex, and you should try and get okay with that, by having more confidence in your own needs and your right to act the way you want. It is worth it. Because for the record: I'm in my thirties now. I'm in an long term relationship. And when I look back on my college years, it is blindingly obvious to me there were all these SUPER HOT guys who wanted to have sex with me and I really, desperately wanted to have sex with them, but I turned most of them down because I was scared about what other people would think.

The times I didn't say no are among my best and most exciting memories. I have no regret about those flings; I wish I'd had more of them, and that I'd spent less time trying to conform in order to avoid other people's judgment. Because seriously, life is short. The time you will have as a young, attractive, single woman is even shorter. You owe it to yourself to have as much amazing sex as you can.
posted by pretentious illiterate at 1:53 PM on May 13 [8 favorites]

Real friends don't make a habit out of cockblocking you from hooking up with an attractive, vouched-for person who is a fantastic kisser. With friends like that, who needs enemies?
posted by hush at 2:22 PM on May 13 [1 favorite]

I in no way meant to come across in a way that implied I was policing the OP's behavior. In fact, I feel quite the opposite. For me, and in my social circles, casual flings are not only widely acceptable, they are the norm and no one bats an eye.

I was merely pointing out that if the OP fears that her intentions are being misunderstood or that her friends may judge her, I would encourage her to look at the way she may be perceived as presenting herself. I never would have thought twice about any of this except for the part about the flirtations/invitation from the best friends of the guy she's talking to. In my experience, that sort of pile-on behavior sometimes happens when a woman makes it clear she's looking for or okay with casual sex. That may or may not be happening here, but I think it's reasonable to offer as another data point to consider.

I'm not judging her behavior, in fact I support it, but based on her question history she doesn't seem to always pick up on social and dating cues.
posted by _Mona_ at 2:40 PM on May 13 [2 favorites]

Well, to clarify: I'm not really sure if I hit on him first or he hit on me first. But that first night, I had zero intentions of sleeping with him- I just wanted to dance and make out. I did not say anything particularly leading to him- he complimented me a lot, danced with me a lot, bought me a beer, pulled me away from his friends, etc. Alice was aware of this (hence her talk with him) so I am sure the others noticed too. On balance I think it is pretty safe to say that he invited me to have sex and I took a couple of days to make up my mind, ish, with caveats. The flirting with the others happened sort of during this, and one of those guys was not there the first night. Also, that guys invite was much more "date-y" and less "hook-up-y" -So I don't think it's necessarily like they'd all talked about it- but there's a weird current of "yes we want to help you get laid" from them sometimes, for both me and him, and a weird current of "but maybe we're a little jealous" sometimes. If I knew what everyone else was really feeling and thinking I wouldn't be in this pickle believe me!
posted by quincunx at 2:48 PM on May 13

You're not in a pickle, you're anxious. That might make sense, I'm not trying to be a jerk about that, but there's no objective problem here that I can see at all.

TBH I think you should cut way back on drinking and socialize with these people a few more times, sober, to see what you think about this whole business and maybe you'll feel more in control. Plus you'll figure out who you most want to sleep with, which is important, because you should probably sleep with him first, and not necessarily with the most aggressive guy.

Anyway, good luck.
posted by the young rope-rider at 2:54 PM on May 13 [2 favorites]

I meant examining what was going through your own heart and mind at the moment you decided to kiss him, and again at the moment you decided to let him kiss you.

There might be a difference between
"what the hell, I'm drunk and I'll deny it tomorrow" or
"he seems to like me, and all these friends seem to think we should get together, so if everyone thinks it's OK, then OK" or
"he's hot and I really want to kiss him [melts] [brain stops functioning] when can I see him again" or
"he's about to kiss me and it's easier to just kiss him than make things awkward [kissing] oh I guess that was pretty good after all, I dunno"

It's good that you don't know what everyone else is really feeling and thinking. It gives you a chance to figure out what you actually want without deferring to what they think you should do right off the bat. I would encourage you to get a lot more clarity on what you personally want and what your own values lead you to do (that is not code for moralistic prudery; your values might well be more carpe diem oriented).
posted by Bentobox Humperdinck at 3:06 PM on May 13 [2 favorites]

I think you and fling guy should spend a little time together sober. And dressed.
posted by SemiSalt at 4:18 PM on May 13

I don't want to threadsit, but I think I'm starting to realize that I am not mature/experienced enough to handle something like this. He probably isn't either. Thanks everyone, this has been elucidating. I also feel like I'm past the age where this is cute and I kind of missed my chance to have that stage. But on the other hand, I did make some new friends and I think it's better off for them and for me if I don't pursue this. Dating in search of a relationship is really more in my comfort zone anyway; I guess I was hoping to circumnavigate that because like I said I am tired of it lately, but I'm beginning to see that there's not really an easy answer and there's a downside to everything.

I'm pretty sure it's not worth adding any more drama to my life. Whether or not that drama is external or internal.
posted by quincunx at 4:33 PM on May 13 [2 favorites]

Dude, you're totally not past the age where having fun flingy sex is fun and cute and you haven't missed your chance. You gain maturity and experience by taking risks. You sounded like you were excited to have a fling with this dude initially, but talked yourself out of it because guilt/anxiety/whatever. This has potential to not have drama and be super-fun and easy and good. I'm worried you're beating yourself up over your anxiety about this, which is super-counter-productive. Go have fun sex if you want fun sex.
posted by superlibby at 4:49 PM on May 13 [2 favorites]

(I also say this as a woman who has kissed/hooked up with a lot of her guy friends. Usually it would be pretty awkward for about a week, and then we would be okay as we both moved on from the hook up. Now, it's totally cool if you don't think you're the kind of person who likes casual sex, but if you want casual sex but are worried about OMG DRAAAAAMMMAAAA and AGH THE FRIENDSHIP AND THE CHILDREN AND FUTURE WEDDINGS, you really don't have to be.)
posted by superlibby at 4:51 PM on May 13 [1 favorite]


I'm reading your question over again, and all the different and conflicting things Alice said are even getting ME confused - no wonder you're confused too. I mean, first she says she had a talk with one of the guys about not doing a one-night-stand with you, but then she says that she thinks you should have a fling. Then she says she has "decided she is okay" with you having a fling with a specific guy.

Is there a reason why Alice is having so much of a say in this situation? That's not a rhetorical question, that is sincere, actually. I'm wondering whether what's going on is that you are asking Alice what to do all the time, or whether Alice is just telling you all of this unprovoked. If it's the former - I would take some time to think about things yourself (it looks like you've started already), and if it's the latter, I'd ask Alice to back off a little, maybe, because these are your decisions to make and not hers. (I mean, if any of my friends told me that they "decided they were okay" with my choice of guys to hook up with, my reaction would be "why do I need your permission in the first place?")

This isn't to say that the opinions of friends isn't valuable (hell, I told my BFF all about the guy I've started dating because I was hoping she'd say he sounded cool - fortunately she did), but it sounds like Alice is kind of treating you like she's your mom, and....she's not. It's a weird power imbalance between you and Alice, it feels like, and I'm curious how that happened because I think correcting that could help.
posted by EmpressCallipygos at 5:05 PM on May 13 [3 favorites]

Alice: she's older, it was her birthday weekend so everything was about her- that's the only reason I met these guys. She invited me to her birthday party/weekend. I'm a newer friend. These guys are like her family, practically (along with her actual brother) and they've known her forever. Also, she kind of likes Dan. And she wants me to be long term friends and hang out with all of them.

But yeah, she has been super conflicted and I can't tell if she's mad at him, me, no one, herself, or what.
posted by quincunx at 5:16 PM on May 13

Yeah, it sounds more and more like your problem is Alice more so than anything else.

I mean, not that you shouldn't do whatever the hell you want with anyone else if that's what you sincerely and truly want to do, but I think that at least 75% of the issue is Alice being super up in your business. Whether you decide to deal with that by telling her to chill out or by just avoiding hookups with that particular group is your own decision, but Alice being this super-invested in what you do and don't do is just confusing things way more than they need to be, and you have the right to tell her that.
posted by EmpressCallipygos at 5:31 PM on May 13 [5 favorites]

Also, she kind of likes Dan.

Bingo. I rest my case.

I also feel like I'm past the age where this is cute and I kind of missed my chance to have that stage. But on the other hand, I did make some new friends and I think it's better off for them and for me if I don't pursue this. Dating in search of a relationship is really more in my comfort zone anyway;

Agreeing with the pp who said you are not too old and you still have all the chances in the world to enjoy "that stage." Hell, you can be in "that stage" for the next 20 years if you damn well wanted to - and more power to you.

Who says hooking up with a friend does not equal "dating in search of a relationship"? My husband was once the friend of a friend who I hooked up with at about your age, complete with the mutual "friend" who tried to cockblock us. (We are no longer friends with that Alice.) And no, I wasn't looking for a relationship, and yet there it was.

When you have physical chemistry with someone plus a lot of shared friends it might mean they are possibly an awesome match for you. But. This can also be threatening to certain other folks in your friend group who like things just they way they are, thank you very much, and who don't want their friends all settling down just yet. They especially don't want their younger friends settling down before they do - and they definitely don't want it to be with their crush - so their "advice" is biased and is not about what's in your best interests. You'd do well to worry a lot less about who Alice thinks you ought to be with.
posted by hush at 5:59 PM on May 13 [1 favorite]

I don't think Dan is fling material. There's too much friend drama and "Alice has psychic dibs" going on ALREADY and there's no way it will go any way but ugly with her, at least. If you want a fling, it needs to be some random person you meet up with at a bar periodically, not someone in a friend group you will see regularly. It needs to be someone who you won't spend enough time with to get romantically attached to.

Here's a primer on how to maintain a casual relationship. As the doctor points out, you need to limit how much time and intimacy you are spending with an FWB.
posted by jenfullmoon at 6:06 PM on May 13

In case you were wondering what it looks like if you marry the guy - I slept with a bunch of guys in college. Several of them were at my wedding as guests. We're still friends 20 years later. It really doesn't have to be a thing. If you don't want to, you don't have to. If you feel anxious, you don't have to. But do it or don't do it because you want to or don't want to, not because you feel as though others will judge you.
posted by RogueTech at 9:14 PM on May 13

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