Dear Prudence,
I have a friend who for the purposes of this letter I’ll call “Tim.” Tim and I have been friends for over four years now, and for the last year and a half at least, I’ve wished for some more distance from him—but I don’t know how to create that without being cruel.
For some background: When we first met, Tim and I were fast friends and quickly fell into a big sibling/little sibling dynamic. I was very much the big sibling: I looked out for Tim, gave him advice, and found him really entertaining. This dynamic persisted for a while, and two years ago, I probably would have called Tim one of my best friends.
Over time, though, the lopsidedness of our friendship started bothering me more and more. Tim really values my opinion and turns to me for support and guidance often; meanwhile, I see Tim as sweet but immature, and he’s not so high on the list of people I’d turn to with hard questions. Part of the issue is that I don’t think Tim has grown up very much in the years we’ve been friends, which has made the gap between us feel bigger. It also means the things I found fun and funny about him in the beginning—things that helped balance the scales of our relationship—strike me as a little juvenile now. Tim has also changed a fair amount in the years I’ve known him—he’s let go of certain passions that made him interesting to me when we met, and in general has become a more isolated person.
One more thing: Tim came out as trans and has been transitioning in the time we’ve been friends (I’m using a name and pronouns that are consistent with his gender identity). I’ve been very supportive throughout the whole process, and have thought very hard about whether some internalized transphobia is contributing to how I’m feeling, but I’m certain now that it’s not. Still, I’m including this information just to say—he’s been going through something big! Which makes me feel all the worse about wanting distance from him.
As I said, I’ve been feeling this way about our relationship for a year and a half now, and I still don’t know how to proceed. At this point, I see Tim about once a month (mainly when he initiates), but that’s still more time than I’d like to dedicate to a friendship that isn’t fulfilling right now. Still, I feel frozen between two kinds of guilt: the guilt of dodging Tim or otherwise not reciprocating his friendship, and the guilt of persisting in a friendship mainly out of obligation. Tim still considers me one of his best friends, and loves me very deeply—which makes all of this that much harder. What would you do?