Dear Prudence,
I have been friends with this one guy since 2017/my freshman year of college. During the first two years of our friendship, I thought my crush on him was obvious, but we only ever hung out in group scenarios. He does have trouble picking up on social cues. And when I say he is oblivious I truly mean he does not pick up on any romantic cues from anyone, even when other people flirt with him. Then COVID happened and we were hanging out online with other friends. The more I hung out with him the more my crush would grow. In 2021/2022 something shifted and we became closer friends, hanging out with each other one-on-one when we were in the same state, kind of completely in sync. So much so that our friends, aware of my on-and-off-again crush on him, would point out that we gravitate toward each other in group scenarios. In 2022, I was leaving to graduate school in London and thinking I would stay there afterward and wanting to get it off my chest (and as a cop-out) only said that I liked him when we were 19/20. He was kind of shocked and asked why I didn’t say it then, but then didn’t say anything else, and we had a heartfelt goodbye before our separate bus rides back home.
Now I’m back from London, he is still in another state, and we are 25. We just spent Memorial Day weekend together with our other friends where once again we spent most of the time gravitating toward one another, and even hung out separately from the group after vacation. I felt those emotions of liking him coming back. We are closer friends now, coming on six years of being friends, able to tell each other anything but also sit in silence. I don’t know what to do with these emotions. Is it too late to actually be upfront with my feelings and ask him out, especially if that might mean losing a friend I connect so well with? Or do I give up and settle for a not-as-strong connection with someone else? I also think he wouldn’t attempt to go out with someone if they can’t be physically in the same state as one another given a conversation the two of us had. He hasn’t ever dated anybody. I go on what seems like one date a year. So we both aren’t actually dating.
—Truly Delusional of Me