Dear Wayne and Wanda,
My girlfriend recently met this guy online and they've now been out several times and she really likes him. She finally invited him to meet us girls for drinks, and I was surprised to see that not only did I recognize him but I actually had a brief thing with him maybe five years ago.
It was nothing serious. We met online and hung out and hooked up a couple times. But we didn't have much in common, and, actually, he was kind of a jerk. He would go hours without returning calls, and after he just completely bailed on me a couple times with no explanation, I suggested we have a talk — and then I never heard from him again. In fact, the other night at the bar was the first I've seen him since.
So what did I do or say? Nothing. I didn't know what to say! My friend is all excited about him, so I just pretended I've never met him and he did the same.
Now I feel stupid, and bad. I feel like my friend should know we have history and I also should let her know he's kind of a jerk. What should I do? Advice?
Wanda says:
Talk about missing the window. Next time, should there be a next time, you extend your hand graciously across the table and say, "Wow, Bob, I haven't seen you since we met up five years ago! I bet a lot has changed since then." Boom. You've acknowledged the connection and the ball is firmly in Bob's court to frame your brief fling and his flailing departure from it however he should so choose.
Look, Anchorage is small. Pasts overlap and sometimes we find ourselves connecting with someone who maybe has had history with a pal. It's almost unavoidable, with the hyperconnectivity of the era of online dating. There are boundaries and it's up to us to acknowledge and sometimes respect them. Dating your best friend's ex-fiance is different from dipping the toe in the dating pool with a dude who once took a sorta-friend out a few casual times.
So, now that you missed the natural window for putting your past on the table, should you tell your lady friend about it? Ask yourself, does it matter to her? Would she care? How important is she to you? How into this guy is she? Is it really worth rocking the boat? Would your revelation create unnecessary drama?
As for outing him as a jerk, well, a lot can happen in five years and for your friend's sake, let's hope he's matured.
Wayne says:
Here's a unique approach — follow closely here because it's pretty complex, innovative and outside-the-box. It's a radical concept called honesty.
Take your friend out for coffee or a drink ASAP and tell her the truth: You dated Bob for a hot minute like forever ago. You guys didn't mesh, so you both moved on. Five years later, when you saw her walk in him the other night, you froze up and didn't know what to do. With every minute that passed, you got more anxious about it, and, ultimately, you couldn't say anything.
You do have a little leeway here. With hindsight, perhaps a first meeting at the bar isn't exactly the right time or place to tell your head-over-heels bestie that you used to sleep with her new flame. And, really, he's just as guilty about keeping this whole thing on the hush as you are — if he even remembers you, that is.
But no excuses here. Do not sit on this. Get it over with. The longer it marinates, the messier this whole thing can and will get. Tell your friend about the connection; tell her you're sorry you didn't mention it earlier; and tell her you hope it works out for her. That's what friends do. And if she's a true friend, she'll listen, be mildly annoyed and then reluctantly understanding, and give you a pass.
About the big reveal about the big jerk — that's unnecessary. Five years is an eon. Maybe he grew up. Maybe somebody put him in his place. Maybe he read the "Four Agreements" because his phone died and it was the only distraction at the DMV. Or maybe he's still a big fat jerk. That's your friend's situation now and not yours anymore … unless, of course, he treats her like crap and ghosts. Then you can go all in on him.
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