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For months, I was seeing a guy in secret. Then he started openly dating my friend. Should I tell her?

  • Author: Wayne and Wanda
  • Updated: February 23, 2019
  • Published February 23, 2019

Dear Wayne and Wanda,

Last year, I started secretly hanging out with one of my friends. I’ll call him “Jeff.” We’d all go out and when the night ended, Jeff and I would discreetly go home together. We agreed from the beginning it was totally casual. Jeff is pretty much famous for being single. The last time we met up was just before New Year’s.

On New Year’s Eve, our whole group of friends was out together, and at midnight, Jeff kissed our mutual friend, “Jane.” We all saw it, it was right out in the open, and afterward they were glued together as if they’d been dating all along. All us girls had brunch the next weekend and Jane said Jeff had told her he’d liked her for a long time and they were hanging out nonstop. She was stoked and I couldn’t bear to tell her I’d been hooking up with him. So I didn’t.

Now I’m in this incredibly awkward place. They’re full-on dating, and Jane still has no clue about my history with her now-boyfriend. I feel like I’m betraying our friendship by not telling her. But recently Jeff thanked me for “keeping our bargain” and not sharing info about our secret fling. Part of me does feel like I’m going back on my word if I say anything, but part of me feels like I’m betraying Jane by staying quiet. And then, I’ll admit, a big part of me is irritated that Jane is apparently girlfriend material while I was just a down-low kind of thing. It feels like that’s the story of my life. Ugh. Any advice?

Wanda says:

Because you’re admittedly irritated, you’re likely not thinking clearly; not thinking clearly is actually the very definition of being irrational, and when we’re irrational, we tend to make poor decisions. (Ever notice how irritated and irrational look so similar?) Let’s think this through: does Jane need to know your history with Jeff? If Jane was your very bestest bestie, or your sister, I might say yes, because some lines are simply too thick to cross. But in this case, no, Jane doesn’t need to know.

We all bring past experiences to the table when we enter a new relationship. Should part of the onboarding into that partnership include a comprehensive review of past affairs to ensure no wires were crossed? Think about how exhausting that would be. With Jeff famously single, as you put it, I’m sure Jane weighed that knowledge when deciding to date him. She may even presume he’s spent time with you or one of the other gals in your group. The fact that she’s with him signals that she’s good with that – or at least OK with that.

Rather than worry about what Jane knows, or what you owe or don’t owe Jeff, I’m drawn to your declaration that these secret hook-ups aren’t new for you. If that kind of arrangement is what you’re drawn to, and looking for, then more power to you; for busy, working adults, a casual thing can be the best solution to sometimes needing some companionship. But if you want more than that – to try dating, to be someone’s real significant other – then start asking for it, and don’t let the Jeffs out there call the shots.

Wayne says:

Let’s just run this one through the Best Friend Meter and see what pops up …

There’s “Keep it on the down low” and then there’s “This is classified Top Secret information and if I tell you I’d have to kill you.” And either way, you’re still telling your best friend every juicy detail, am I right?

I mean, that’s what best friends are for. You talk about everything. And I mean ev-er-y-thing! Your highest of highs, your lowest of lows – your best friend hears it all. That includes embarrassing one-night hook-ups and amazing long-term flings on the DLs with a certain friend of a friend. Your best friend knows when to provide perspective and when to just sit back, listen and let you glow or vent or meltdown. Your best friends also know when you’re keeping something from them, so good luck hiding a secret like this.

When you and Jeff were hooking up, Jane didn’t suspect anything and you didn’t tell her anything. Which means she’s not even a close friend, much less a bestie. Which also means it really was none of her business then and it’s not your business to tell her about that business now.

If you need to get something off your chest about how things played out with Jeff, tell your real bestie. If you don’t have a real bestie, tell a shrink – they’re really good at listening. But don’t go blowing up a nice little blossoming relationship because you’re confused and irritated. Trust me, neither of them will consider you a friend anymore if you do.