Am I overreacting? I can't tell.
My (former) friend (male) has really poor boundaries. It's always been a bit of a problem - he asks fairly intrusive questions often (wants to know about my past, my relationships, even has asked about my sex life - that sort of thing), is known to message at all times of day and night and keep messaging until he gets a response at times, and it's not unusual to tell him I went out on a Friday night and for him to ask - where did you go? who did you go with? what did you talk about? It's always left me feeling a little odd but I've used various strategies over the years to deflect/deal/change the subject etc. We talk every day online and if I don't respond to a message he'll always follow it up with another. It's been intense, but a friendship I still gained a lot from.
About a month ago we had a fairly free and frank conversation about our love lives - he asked me a lot of questions, and we talked about his too. He didn't like some of the advice I gave him so said afterwards he was never talking to me about dating again. Fine, I said, also feeling a little relieved as I didn't like his questions about my love life anyway.
Over the past month we've still talked often (most days) about some big things too, and he has asked me about my love life. I have still not asked about his - I don't actually really care that much, and he had said he didn't want to talk about it, fine. But - it's really hard to talk to someone every day and avoid asking them what they are doing at the weekends/evenings as if he was dating I didn't want him to feel awkward about telling me. So we keep having these odd conversations about what I am doing, in which he didn't say anything about what he was up to in his spare time.
Then he started saying things like "I've been out so much recently" and "I need to drink less" "I need to get some sleep", and still I didn't ask. It came to a head yesterday when he said he'd had a great evening and I asked what he had done and he said that he wouldn't tell me because it's that thing we won't talk about.
I reacted badly - said he'd been hinting at me to ask - and that I found it really awkward and weird not feeling like I can ask him anything about his life. He said that's too bad, that's just the way it's got to be because he's not talking to me about his love life anymore.
The conversation really upset me and now I am wondering if I even want him in my life, but also wonder if I am being a hypocrite and unreasonable for not letting him assert HIS boundaries? I just don't know and would welcome advice.