Alright, so it was my friend's birthday. It was a pretty small get together, basically my friend and his wife, and their two roommates (one guy and one girl, I know they've hooked up but aren't a thing). The male roommate I'm going to call Joe.

I get their late afternoon, have a few drinks while we play cards and stuff like that, and eventually another woman shows up. Let's call her Jill.

We're all having a great time, and as we're all drinking, we're all getting progressively more flirty. Between games, me and Joe (the roommate) are talking to Jill. She talks about all this stuff she wants to do, but her husband wouldn't even let her (silly stuff, like just going to karaoke or a gun range, or playing D&D). I start to joke, "Well you's husband seems kind of... (clearly was going to say "lame", but it's never a good look to belittle another guy)... well, you sound a lot cooler than he does". She kind of chuckles and says, "Yeah, that's probably why we're getting a divorce."

So, at this point roommate Joe completely shifts gears. I don't know if some guys have seen success, but he just starts telling her (pretty openly) how much he wants to fuck her, or eat her out, and she should just come back to his room.

At this point, my friend's wife (who up until this point, I'd always had a pretty firm believe just didn't like me very much) becomes the greatest wing-man of all time. She rags on him and his brothers "having tiny dicks" (I guess she's known him and his brothers since they were young), and tells her there's plenty of space if "you and and jcorb want to have a little alone time".

Joe goes full-blown try-hard, telling her how much he wants to eat her out, Jill and my buddy's wife are laughing about it (couldn't quite read the situation). Somehow, conversation shifts to if he and her husband had just had a fight or not, she just kind of breaks down saying they've been fighting and talking about it for like a year, but he'd left a few days ago and said he wanted a divorce.

Somehow in this situation, I wind up hugging her, she kind of cries into my shoulder, I must have said something that got her spirits up (just something like "You've got this."), and she seemed completely fine. After that she starts dancing to music, grinding up against me, and telling me to smack her ass.

At this point, my friend's wife says "Well it sounds like you guys have been thinking about this for a while (about the divorce), so you do whatever you want to do. And you've got two men here that both clearly want to fuck you." She looks us both over, and goes "I think you need to fuck jcorb (me); he's going to take care of you, and make sure you have a good time." (again, I have no idea where that came from, but Jill seems to react to the suggestion and slides into me, with me wrapping an arm around her).

She says "Well, I'm not going to fuck anybody tonight," at least not until he actually gives her divorce papers. They've apparently been together since high-school, and were virgins when they got together, so clearly a lot of baggage. She's pretty wasted at this point, although she does slide her phone over to me (clearly not trying to let anyone know), with my name punched in and waiting for my phone number to add as a contact.

Now, this is basically the end of the night. Joe puts one more plea out there ("My door is going to be open, so if you decide you want me to fuck your brains out, I'll be in my room") and bounces. Me and Jill go lay down on the couch, but unfortunately my actual friend has been doing other stuff much of the night, and winds up sort of cock-blocking me because he's hanging out watching some fucking documentary. By the time it's actually over, she's asleep. So, I move over to the other chair and go to sleep myself.

Jill and I wake up to my friend and his wife already awake, making pancakes for us (sort of a hangover ritual for the three of us), we talk a bit about plans for the week. Jill has a crazy work week, but then will be off for a few weeks, so we talk about making plans. She basically says "keep me posted", and we both leave (she has to get back to her dog and get groceries, otherwise she said she'd have hung out for the day).

Me, being a fucking idiot, forgot to actually ask for HER number until after we'd already left. And she was so drunk, I don't even know if she would remember asking for my number the night before.

Here are my personal take-aways:

  • Joe, despite being objectively way more attractive than myself, wound up doing me a favor by trying so fucking hard. I looked way more cool by comparison, while still giving a good opportunity to escalate.

  • Hey, humor actually does help! When I'm drunk, I'm surprisingly charismatic, and felt like the life of the party (even the female roommate, I'm pretty sure made a pass at me once that night, or at the very least ran her hands over me; I don't remember the context). I distinctly remember everyone cracking up when she mentioned owning a Tesla (fun fact: she is the bread-winner in their relationship), and I reply "I am so wet right now."

  • As TRP seems to always stress be careful how much validation you give. I let her know I was definitely interested, but I wasn't fawning over her, like Joe was.

  • Pre-approval from females is worth its weight in gold, apparently. Even though I was so sure that my friend's wife didn't like me or thought I was a loser, she was definitely "Team jcorb", and it clearly made a huge difference. Conversely, she straight-up cockblocked Joe.

My big questions:

  • Should I have tried harder to actually get laid that night? Or by respecting her boundary of "not wanting to fuck anyone until getting divorce papers", maybe there's a possibility of that still happening?

  • For that matter, do you guys think there's an ethical conundrum in this situation? Like, had I fucked her, she even said "there would be no going back" (that was the reason she didn't want to). She's clearly hoping her husband changes his mind about the divorce, and I'd have a hard time not feeling guilty if I were the one to sabotage any change of that. I've not even really met the guy (maybe he was at a party once?), but I'm not trying to ruin anyone's life.

  • Should I ask my friend or his wife for Jill's number? And if so should I do anything with it (ie. "hey, why don't we meet up for target-practice and I'll teach you how to shoot?")?

  • Should I just write the whole thing off as "a really fun night", but that she was purely looking for validation? Just carry on as though she doesn't exist, but if she does reach out, only then pursue anything? (I do want to add, it is incredibly rare to find a woman who makes her own money, and apparently makes quite a bit more than even myself; the idea of a woman who is financially-ambitious is very appealing)

I mean, when it's all said and done, I had a fun night no matter what. But I try to look at everything as a learning experience, and just trying to reflect on what I could have or should have done better?