Swipe to the (Mr.) Right



Dear Dharma,

My best friend, Brian, has spent the last six months – how shall I put this politely? Playing the field on Tinder…he has dated and hooked up with an astounding number of women as part of his attempt to get over an unexpected and difficult breakup.

However, as his New Year’s resolution, Brian has decided he wants to give up dating around and just enjoy spending time with friends, getting back into his fitness training and only dating women he can see having a relationship with.

I’m happy for him, but here’s the problem – he’s still telling his single male friends how great the single life is if you play the field all the time, see a different woman every week, and keep everything casual.

Normally, I would just chalk this up to guy talk and let it slide, but one of the guys he’s encouraging to live the wild bachelor life also happens to be a guy I really like.

I met John through Brian, and we’ve had a low-level flirtation going on for about a month now. I know John has some interest in me because he asked Brian about the kind of men I like to date. At the time, Brian asked me what I thought of John, but I’d only met him once or twice, so I was a bit noncommittal.  I said I’d just like to let it play out naturally. (Brian is a notorious matchmaker who loves to make connections).

But now, I really like John, and it bugs me when Brian encourages him to go out with tons of women or when he casually mentions he might set John up with one of his former Tinder dates.

I haven’t told Brian I have feelings for John, partly because I don’t want him to do his matchmaking thing and partly because I’m just not ready to share it yet. But now I feel like I have to tell him – I know Brian would feel terrible if he knew he was doing/saying something that upsets me.

My problem is, telling him puts Brian in a bit of an awkward position – he’ll either feel like he can’t speak openly in front of me or he’ll feel compelled to reverse himself and tell John not to date around (or both).

Got any advice on how to thread this needle and let Brian know why his pitch for the single life bugs me without making things awkward for him?

Moving Pieces

Dear Pieces,

Wow – I considered going back to school to get my degree in something or other just to follow all of that.

But I think I’ve got it figured out, and I honestly think you need to employ the KISS strategy here – Keep It Simple Sweet.  Your need to overthink this is making things way more complicated than they need to be.

Assuming we’re all adults here, just tell Brian you like John.  He’s a big boy who can probably handle this level of information.  You don’t need to tell him that it bothers you that he’s been encouraging John to play the field – because in actuality, without knowing you liked him, Brian wasn’t doing anything wrong.

Bottom line is after knowing John for a little while, you’ve decided you’d like to take things further.  The end.

If he jumps in and wants to start his regular match making, tell him that while you appreciate his desire to help, you’ll take things from here.

And then do so.

You’ve obviously got a connection with John that is reciprocated, so put your energy into building that instead of stressing over what Brian is doing.



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