Once had a strange relation with an ex bf (I’m M43 bi) and when we used to date I always liked to pay for his stuff, going out, etc. But then we got apart and were still friends… I just felt like paying for some of his stuff even though we were not together. I could feel he liked it a lot and took advantage of it for some time. Apparently he didn’t want it anymore when he got another bf… but I still chatted with him and without being clear about it he let me know one or another expense he had and I made the deposits but it was all silent - we never actually talked about it.

Does anyone have / did anyone have these kinds of connections with boyfriends / girlfriends that are both friendly, maybe romantic, sexual (or not) and somehow is also very satisfying because it involves money, interest, taking advantage, but also caring, close and intimate?

This is usually what really gets me!

It was just a deep connection as boyfriends and then we were not boyfriends anymore, he found someone else. But while the relationship was going on, we started having some different agreements between us. Nothing too big… but coming specially from him, but from me too. I would take business trips because I had too, and he’d always be waiting for gifts from the trip. When we went out to dinner, it wasn’t agreed upon or demanded, but it was obvious that I would offer to pay and he’d say “of course”, and so on. When we broke up he had found someone else and we almost instantly became friends because I really liked him and wanted to keep in touch with him. Giving less than a month, he started telling me the places they were going, dinners, parties, or trips arranging together. Together with those stories, there would be also involved a mention about money / expenses involved / places they wanted to get to know together / special things he wanted to buy, etc, and also always mentioning how demanding I was, questioning if I truly liked him as a friend, if I really wanted to keep in touch. And there was a day that he stated more clearly that I was very demanding as a friend, that I need to show him I really liked him and wanted to keep in touch and started to put a lot of pressure for me to be a better person, be more present, and watch out for when he wanted to talk or vent, etc. During this times I would always offer if he wanted help to pay for a dinner out with his new boyfriend / a help choosing a present / help with ideas for gifts / help with his car repair / help help help - he promptly ALWAYS said yes. But after this period it seems to me that we became closer and closer as a friend and he started opening more and more details about his new relationship and how good it was (even pointed out some specifics about how much better he felt and more he loved the new boyfriend and he had never felt that way about me). But he insisted I could be a better friend than I could be as a boyfriend… this carried on for a couple of years. Always involving borrowing money I never got back, always small to small-medium amounts (from anything like $10 to $50… $90), but it was constant. We got to the point of certain agreements between us and he was very certain about them… like if I truly wanted to show I supported his new relationship I should be ready to pay for at least one night out a month (first his bill… then both…), etc. And we got deeper and deeper. Anyway this has been quite some time ago, but I still miss him… we got apart with the time. But I still think of writing to him just to ask how’s life…