Dear Breakup Girl,

I recently started dating this girl and I like her very much. But everytime I see her she insists on bringing her best friend along. She expects me to bring a friend to keep her friend company. I didn’t mind this the first few times but now it is way outta hand. When she calls me she has her bestfriend on three-way. Plus she tells her best friend everything about our relationship and I feel that some things should be left between us. How do I let her know this without offending her?

— Anonymous

Dear Anonymous,

Yeah, well, as three-ways go, that’s not so much the kind that people fantasize about. Bringing A Friend — on a date, never mind a phone call – almost always means Take a Hint. But I wonder if in this case, we might want to reinvent the third wheel.

She (they) does (do) call you; she does want you to bring a friend for the Friend (thus upgrading her from Chaperone). Except for the telephone part, there’s something about it that’s a little Jane Austen/Edith Wharton — you know, where it’s unseemly for a single woman to be alone with a man to whom she is not betrothed, or with whom she is not having an affair.

So I don’t know, maybe this gal is being sort of old-fashioned — yes, awkwardly and annoyingly so — because she’s new at this dating thing? Tell her you like her friend, but you LIKE-like her. Enough to be (talk) alone with her sometimes. Ask her how she feels about that. Is she comfortable? If not, why not? What would make her more comfortable? If you ask, you won’t offend. Also, you can’t control what she reports to her friend, but yeah, you could get at it like this: “Hey, blankety-blank is really special to me — and it’s even more special if it’s something that only the two of us know and talk about.” All in all, here’s your spin: it’s not about dispersing the crowd, it’s about craving her company.

Love,
Breakup Girl

P.S. On a peripheral note, scientists at Breakup Girl Labs are hard at work on “twenty-three way calling,” which will allow users, post-breakup, to explain “what happened” to all mid-level acquaintances at once.

This advice was originally published September 14, 1998.