Dear Lovehacker, Let me preface this by saying I am not an attractive man. And I mean that in all senses. I'm fat, ugly, self-loathing, milquetoast, and have absolutely no confidence. I'm in my mid 30s and have long ago (mostly) made peace with the fact that I will never have a fulfilling love or sex life.
So anyway I met "L" a few years ago and we became close friends. Smart, funny, sweet, kind and beautiful. She also has a fiancé, "J", who's a pretty great guy and I regularly hang out with both of them. (You can see where this is going, right?)
At first I crushed on her hard, but I've gone through the whole fall for an unattainable woman thing before, with predictable and unfortunate results, so I quickly let those feelings go and made sure to only think of her as a friend. She didn't make it easy because she's a very touchy-feely person and I'm not accustomed to the casual touch of attractive women, but I persevered. When she and J got married, I had a blast at their wedding, made a fool of myself on the dance floor, and was genuinely happy for them.
L had mentioned several times that she thought I was good looking, often loudly to friends and complete strangers alike. She even told me once that if she had met me before J, things may have gone differently. I always just thought she was just saying stuff like that to try to boost of my self-esteem.
Cut to the other night. I went to a buddy's house for game night. L and J were there too. At the gaming table I sat next to L with J on the other side of her. Beer was flowing generously, though I was the only one not drinking. At one point my buddy's cat jumped on to my lap. I petted him for a bit and so did L. Eventually her hand slid off the cat and onto my thigh. At first I thought the alcohol had made her extra touchy-feely, but then after the cat jumped off, her hand slowly moved up my leg. I froze. I didn't know what to do. She slipped her hand underneath my shirt and started raking her nails across my back and side. And it felt good. Really good. I had no idea I was into that kinda thing. Look at me learning about myself. Anyway, her turn comes around and she retrieves her hand much to my relief and disappointment.
A little while later we all decide to take a to pause the game for snacks and restrooms. It's customary for L and I to take a smoke break during these pauses. We stepped out, but instead of standing on the back porch in front of the sliding glass door like usual, she walked to the side of the house away from doors and windows and prying eyes. I followed but kept my distance, and asked her what was going on. She was evasive and wouldn't directly answer any of my questions. Instead she asked me if I've ever had a woman take control, and then pressed her body to me. My previous train of thought derailed, and I instinctively put my arms around her and held her tight. We were millimetres from kissing, but then I had a sudden thought of J inside the house not 15m away. It was difficult as hell, but I pulled away. She was grinning.
We went back inside, and the rest of the night passed quickly. She would sneak in a touches and gropes whenever she could. I could have stopped her, but I didn't, and I liked it. At the end of the night, as the three of us were walking out together, a very drunk J realised he forgot his jacket and ran back inside. The moment he turned his back, she quickly drew me in and licked my cheek. Turns out I don't find that hot. More learning there. But the intention was clear. Then we parted ways.
So, yeah, I have no idea what to do now. I mean I know I should try to get some answers from her, but I'm not sure how to go about it. Her friendship very is important to me, and I don't want to damage it. And I definitely don't want anyone else to get hurt. Maybe it was a one time thing. Perhaps she was just teasing me, and so long as I don't bring it up, it won't be an issue. Or maybe they're opening up their relationship and she wanted to test the waters. Probably wishful thinking on my part.
But what if she simply wants to have an extramarital affair behind her husband's back? I've made so many mistakes through inaction in my life, maybe just this once I should do something wrong on purpose, eyes open. I will never have the chance to be with a woman this gorgeous again. I could live in the moment as hard as I can, then bear with inevitable disastrous fallout.
And that, of course, is a terrible idea. So I guess my question is, if I find myself in a situation with her that is heading for a place I know is wrong, but every cell in my body demands I go with it, how do I generate the willpower to say no? Greater men than I fail at this all the time. Thank you, Discombobulated
Hoo boy, I'm glad you've written to me before you've done anything, because right now you're on the path to sticking your dick in a buzzsaw. Not that I don't doubt that the sex would be great and she's an amazing person, but the likely fallout would be far worse than you realise.
Now in general, I don't believe that sex necessarily ruins a friendship, but in this case, we're talking about consequences that go beyond just the two of you.
Let's game this out a little so you understand where I'm coming from here. You hook up with her. In all likelihood, she does not have an arrangement with her husband for a little off-leash time which means that she's just cheated on her husband with you.
If and when this comes to light, then you will have seriously hurt J, someone who trusts you and who has been a friend to you. That's a pretty shitty thing to do to somebody you think is a great guy.
Then there's the fact that you have overlapping social circles. This is the sort of gossip that shoots through like wildfire and people will have very strong opinions about who was in the right and who was in the wrong. You will more than likely find a whole bunch of your friends do not appreciate you being instrumental in damage to L and J's relationship.
Now let's say that through all of this, L and J manage to pull through L's infidelity and make things work. One of the things that would almost certainly be part of their reconciliation is ensuring that she wouldn't make the same mistake again. That means never seeing you again… which in turn would likely mean you being exiled from the social circles where they are fairly prominent.
That's more than just ruining a friendship, that's ruining many friendships, potentially a marriage and needlessly hurting more than a few people in the process.
And let's say that, unbeknownst to you she's having problems with J. Then you're less a sex partner and more the hammer she's dropping on his nuts. Trust me: the sex ain't worth it if you can't live with yourself afterwards.
Now, odds are that she was drunk and feeling a bit horny and she decided that maybe a little naughty fun was in order. Even so: that's the sort of behaviour that can strain any friendship, especially when the potential fallout is pretty damn immense.
So what do you do? Well to start with, I'd say jerk off. Horniness has a tendency to suck all the blood away from your brain and suddenly your balls get veto power over the rest of your decision-making process. It's a lot harder for your dick to make stupid decisions when your brain isn't floating in a pool of sexual frustration.
Next, you lay down some boundaries with L. You tell her, "Hey, I don't know what was up with the other night, but that made me really uncomfortable. I like you, but you're married to J and the way you were acting made me feel awkward around both of you. I don't appreciate being teased and I don't want to end up being part of a problem between the two of you."
Now the ball's in her court. She may pretend she doesn't remember; you pretend to believe her. Same with if she says it was a joke, you were mistaken or any other variation of "it never happened." Just go with it. Being "right" in this case is less important than making it clear that you don't appreciate being put in that position.
And then… let it drop. If she's as cool a person as you say, she'll realise a line was nearly crossed and be careful not to do it again. If she gets a little buzzed and handsy again… well, put some distance between the two of you, make sure you're not left alone together and try to avoid hanging out with her when alcohol is involved.
I realise what you want is incredibly powerful, especially when it drops into your lap and starts to wriggle. In other circumstances, I'd tell you to go for it. And who knows, maybe in the future circumstances will be different. But right now, if you did give in, you'd regret it far more than you'd enjoy it. Trust me: I have been there, done that and printed the t-shirts.
As hard (fnar) as it is, maintaining some boundaries is the best thing you can do here.
This story originally appeared on Kotaku.
Harris O'Malley is a writer and dating coach who provides geek dating advice at his blog Paging Dr NerdLove.