Dear Annie: I'm a 32-year-old single woman facing a predicament. I've been friends with a guy named "Stan" for a few months, though we haven't actually talked in over a month now. We were acquainted in high school, but we lost touch after a short while. Stan and I went on a couple of dates, and I thought things were going well, but then he asked if we could just be friends. If we hadn't ALMOST hooked up, I would've been fine with this, but because I thought he was still interested in me as more than a friend, it took me by surprise, but I agreed to it. We continued to talk and hung out once more; however, I had expressed my feelings for him a total of three times, and the third time, he came close to blocking me. Stan had made it very clear to me that he doesn't reciprocate my feelings, though when we first started talking as friends, I had been optimistic that eventually we could be more than that. The two times that I've messaged him since, he's left me on read, though he sporadically watches my Instagram stories. He's explained that he's not ready for a relationship, yet I've noticed that he follows numerous women and he's on a dating app. He's also mentioned that he's experiencing family issues, but because we've only known each other for a few months, I felt that was too personal of a subject for me to provide input on. I'm afraid to initiate a conversation with him because I don't want to risk arguing and (possibly) consequently losing a friend, but at the same time, I feel like he's hiding some things from me. I'd like to let him know that he can trust me, but it remains unclear to me as to whether I can trust him or not. The last time Stan and I talked, he asked me to give him space because I was making him uncomfortable, but now I'm wondering if he is just trying to phase me out of his life. That was almost a month and a half ago. Please help. I have no idea what to do about this. &8212; Crushed OverthinkerUpdated: Sat Jan 28, 2023