Hi Dan, I'm a longtime fan and this is the first and only time I've felt like asking your advice.

TL;DR: 2.5 years ago I hooked up with a girl who "got away" from one of my close guys friends and I am conflicted about whether to tell him.

Full version: I have a guy friend, let's call him John; he's not a best friend but he's my closest guy friend in the town where I live. We've been friends since 2009.

In 2012 this girl, let's call her Jane, joined our friend group. I noticed a mutual attraction between her and I but I had other options and no reason to pursue her. She started hooking up with/casually dating John. She warned him that she didn't want something serious/with expectations, but things progressed and he told her he loved her, right before he had to leave town for a few months. So he left and all parties were single. Jane proceeded to add a few more notches to her bedpost.

A month or so later, Jane is at my place after I hosted a daytime event. Everyone else had gone home. We were just passing the time with drinks and watching TV. I decided to make the exciting (at the time) choice and pursue the opportunity: I put my arm around her, and things moved to spooning in my bed while watching the TV but no kissing. I felt like there was too much potential for a strong friendship between us to make it a full-blown hookup. Near the end of the night I offered to go down on her with nothing expected in return. I put my full energies into the task and then she returned the favor; still no kissing, and she left.

No physical contact ever happened again between her and I; we each told our own trusted friends who we figured would never have contact with/spill the beans to John. John returned to town and hooked up with Jane a handful times more but eventually they grew apart and he got over her. Neither of us see Jane any more; she left our friend group.

To this day I have been conflicted about this when hanging out with John. I'm pretty sure he doesn't know; For the first year or so after it happened I was pretty sure that he would've been mad to find out but now I wonder if enough time has passed. I wonder if he would forgive me now. I also wonder, if I were to confess, would it be for the best to give an apology gift? Or maybe one opportunity to do some mild physical harm to me?

Wondering if you have advice.

Conflicted To The Core

My response after the jump...

TS;PR*: Keep your mouth shut.

Long version: You betrayed John, your good-if-not-best friend, when you made a move on Jane, a girl you knew John had feelings for.

Technically John and Jane weren't together, CTTC, but they weren't exactly exes either—so we're not talking about the supposed "betrayal" of hooking up with a friend's ex. (I don't think friends' exes should be off limits**.) We're talking about the certain betrayal of moving in on a girl that your good-and-temporarily-absent friend hoped to get more serious about upon his return. Things ultimately didn't work out between John and Jane, of course, and it's likely their relationship was destined to be short-lived. (I almost typed "destined to fail" but a relationship shouldn't have to last forever, i.e. go and go until someone dies, to be counted a success.) But you didn't know that the night you went down on Jane. All you knew was that John was in love with Jane and that he had hopes. And if things had worked out—if John and Jane wound up together, if they got married and had kids—you would be sitting on a potentially explosive secret for the rest of either your friendship or your life, CTTC, whichever one ended first.

So, yeah, what you did was kind of shitty. But with Jane out of the picture, and with it being unlikely that John will find out about the affair, I would urge you to keep this to yourself. If that's not who you are today—if you're a more trustworthy friend now than you were then (perhaps thanks to this experience, i.e. you wouldn't do something like this again because it helped you realize the the angst of this kind of betrayal isn't worth one lousy orgasm)—there's no reason to complicate your friendship going forward by clueing John in on what a shit you used to be.

* "Too Short; Please Read."

** Do you know what straight people call dating a friend's ex? Betrayal. Do you know what gay people call dating a friend's ex? Dating.