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When an old fling resurfaces -- and is dating your best friend

  • Author: Wayne Wanda
  • Updated: September 30, 2016
  • Published April 14, 2016

Dear Wayne and Wanda,

My friend recently started dating a new guy. She told us about how much she liked him before finally introducing us to him. I was surprised to see I knew him; I went out with him a couple times a few years ago and we had sex once or twice before deciding we weren't really compatible. It wasn't really a big deal, and we haven't talked since then, except maybe in passing at the bars.

I think neither of us knew what to say, but the second my friend left to use the bathroom, he pulled me aside, said he really likes my friend and asked that I not say anything about our past. He was afraid it might have ruined things, and frankly, it might have. My friend has always been weirded out when one of us likes someone who another one of us has previously been with or dated.

So I haven't said anything. That was a few months ago. They are more serious all the time and I feel seriously uncomfortable for not saying anything. Should I tell her?

Wanda says:

What would the point be of saying anything? "Hey lady friend, you know that guy you really like? Well, I realize telling you this may destroy the very intense and wonderful connection you two share, but several years ago he and I had a brief interaction that was unremarkable and bland."

I would understand your need to confess if this dude were notable in your backstory, someone you were deeply intimate with and connected to, but it sounds like you barely remember his name.

We don't have to tell our friends everything, and Anchorage is so small that sometimes, crossing dating wires with our friends feels unavoidable. But you should learn from this. Why would you agree to keep a secret from a good friend on behalf of a guy you barely liked enough for a third date? I'm sure you'd be displeased with friends who acted similarly. Don't do it again.

Wayne says:

So, you let some dude you slept with a few times convince you to stick to his script with your good friend? Nice. Enjoy your Least Supporting Friend trophy.

While the door has closed on telling her that you and Lyin' Gosling have a history, you should get your notebook ready and prepare a speech. Because if they keep dating, this one is eventually going to bite you in the butt. And not in the fun way. All it will take is running into a mutual friend who knows you both or one slip of the tongue (his or yours) and the jig is up. The truth will come out and you will have some explaining to do … if she even wants to talk to you anymore.

Better hope they break up soon or you'll be walking on eggshells for the rest of your friendship.

Dear Wayne and Wanda,

I was out with my girlfriends the other night when "Paul" approached our table. My friends knew him. He and I hit it off, and when he left, he got my number. I was really excited.

But the second he left, both of my friends said not to go out with him under any circumstances. They said they've known him for 15 years, that he's a jerk and doesn't respect women, and maybe even was abusive with an ex. I was alarmed and disappointed, but also second-guessing them. I mean, he seemed awesome and all that was a long time ago. Shouldn't I give him the benefit of the doubt and get to know him on my own?

Wanda says:

It's true that people can change. We all do stupid things when we're young. And most of us grow, change, learn and mature over time. It's also true that sometimes, people don't change. And it's true that the only way you will know for sure is to hang out with Paul on your own and judge for yourself.

However, the fact that not one but two of your lady friends are throwing flags would raise a red one for me. If you do decide to go out with Paul, make it a short commitment -- appetizers, not a day trip to Girdwood, for example. And be cautious; don't discount your friends' input just because it wasn't what you wanted to hear.

Wayne says:

If your friends say wait, you must not date. Sorry, still buzzing on "American Crime Story: The People vs. O.J. Simpson," a tale about another seemingly-charming-but-not-so-nice guy (allegedly).

Seriously though, how many thumbs down do you need? If two close friends advised that a dress looked frumpy on you, would you buy it? If two close friends warned you not to eat the oysters Rockefeller at a new lounge, would you order them? If two close friends said the ice is thin on the pond, would you still go skating?

You could try to prove your friends wrong, but they won't want to hang out with you when he's around. More likely, it sounds like you'll prove your friends right if you call Paul.

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