Dear Prudence,
I (she/her) have been best friends with “Mary” since we were 19—about nine years total. We met in college, where initially I thought she didn’t like me! This is probably because she has a contrarian personality—often critical of media, jokes, phrases, public figures, and cultural artifacts other people love—and won’t mince words when expressing that she dislikes something in the presence of those people. She’s had this sort of taste since she was, like, 12. This has led some mutuals to voice that they find her standoffish or too cool.
Mary IS cool, and also generous, intentionally kind, and the most excellent listener I’ve ever met, once she is out of her shell. She has taught me a lot about what it means to be a good friend. She has shown up for me every time I needed her to. Her tastes have influenced mine massively, and she likes my art genuinely. I’ve grown to see her sharpness, her ability to see where other people end and she begins, as some of her best qualities. In fact, it’s inspired me to limit some of my own people-pleasing tendencies.
But here’s the thing: I’ve lived long enough to realize that one’s best qualities are also at least sometimes one’s most challenging qualities. Lately, I’ve been feeling a little tired of Mary undermining things I like—whether it’s a pair of funky shoes or a new indie film or an opinion about implementing our (shared) socialist politics. Sometimes she’ll contradict me about something mundane while with a group of friends, and I recoil into myself. I’ll wonder if I’m taking it (and myself) too seriously or if she’s being a little socially ungraceful. Sometimes she contradicts me privately, and I’ll wonder—if we aren’t totally at odds, why can’t you just “yes, and” me? Is that too much to expect?
I try to notice whether she’s doing this equally to everyone, but it’s hard to tell. It comes off stubborn, unwilling to consider that I might have a point. It creates an inhospitable environment for any type of conversation besides a debate, which I rarely want. Or a “well, agree to disagree,” which sounds formalistic and a little passive-aggressive. And I worry that if I do suddenly begin to go to bat for my opinions and tastes without explaining anything, it’ll throw her and others off.
Either way, do you have any advice for whether and how to approach her about this? I’m struggling, because I don’t think her outspokenness and well-developed critique are always a bad thing!
— I Have Taste Too