Search Results: dating questions

In January 2025 I was chatting to a man briefly on an app. I liked him and he suggested meeting up. Things were going fine, we talked about expectations etc. prior to meeting. He also mentioned that he’d had a stillborn baby in his last relationship. It left me speechless but I offered a lot of empathy. After that admission, he retreated a few days later and said he didn’t see us going anywhere, which contradicted everything we’d chatted about and our similar values.

Fast forward to September, he reached out again and we ended up chatting for a couple of months every day. He arranged a date with me. The pace was slower this time, we didn’t jump right into talking about the serious stuff. Consistency was there, he was incredibly kind. We met for the first date and it was nice. We laughed, he told me a little more about what he’s been through (loss of brother, rehab, stillborn baby, loss of partner, rehab and then turning his life around). We made physical contact and hugged and he told me I looked lovely. He arranged a second date before the first ended and I met him again. We chatted a bit more, not too much in-depth but enough for me to know he liked me. We admitted we liked and were attracted to each other. We hugged again and before that date was over he arranged the third. We met for our third and went to the cinema. When he said goodbye I could feel more closeness in his hug and goodbye. This time he never arranged a fourth date.

I noticed more intimacy in his replies after this date and he said he hadn’t been sure whether to kiss me. I said I was happy for that to unfold naturally. But after the kiss question? I noticed a slight stall, things weren’t moving. When I asked if he still had time for dating, he deflected the question back to me and side-stepped. Basically saying we’d been busy and that distance doesn’t help along with us not being ‘excited’ to talk to each other. A bizarre reply, because it contradicted his actions completely.

My question is complicated for a complicated world. The rules of dating are not what they once were. Who usually pays for a first date these days? Do you split it? Does the woman pay if the woman does the asking (which does happen some). Does the man always pay as a traditionalist? Does the person who is in better financial shape pay, and how would you know that?