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.