Dear Prudence,
Many years ago, I really thought I (30F) was in love with a guy. We had an extremely emotionally intimate friendship: deep conversations, shared passions, and grief—but nothing more than hand-holding. I never said anything, although I learned later that he may have had some idea I had a crush. It was unrequited, I helped him ask someone else out, and I kind of cut ties. It took me much too long to get over not only him, but also the insecurity and self-doubt for ever thinking that the feelings were returned. After some time, we reconnected and were on good terms, although I still kept a distance.
I went through old texts recently, and it made me really miss my friend. We haven’t chatted in a couple of years, but I’ve been aware that he has lost some family this past year. I avoided reaching out directly by habit. But now I feel like a bad friend. Part of me wants to reach out now just to genuinely say that I’m thinking of him. But all the gremlins in my head make me unsure if I’m A) overthinking,
in denial, C) right, or D) lonely. I guess my question is: Am I being overly sentimental, or is this normal to try to reconnect with a friend after emotionally untangling them being your hopeless crush?
—E) All of the Above