Anonymous wrote:Woman here. He started taking longer and longer to leave my place and started trying to hang out, such as having brunch after our hang outs. I never wanted him as more than a NSA hookup, but I was between boyfriends so I let him promote himself to my “boyfriend” while I kept any eye out for the right guy. When I found my now-husband, I ditched my FWB-turned-boyfriend. My FWB took it hard, but I was just never all that into my FWB.
All of this is to say there’s a reason you’re FWBs. If you try to deepen things, it might happen, but that there is a reason for that initial hesitance and it will still be there. Odds are any relationship won’t last. Start over with a man who took you seriously from day one.
OP here. Not 100% sure he is trying to transition, but he is lingering longer and doing some stuff he use to not. We both have expressed interest in the past, but at different points in time.
I hear you on if the relationship would work. He is someone that really doesn’t date/very independent. However, I am not exactly Ms. Relationship. I have had three boyfriends in my adult life (longest being a 1.5 years). My last relationship was 11 months with a ‘relationship-minded’ guy and went on longer than it should have. I felt so smoothered. It’s been 5 months since we broke up and I am know considering getting back to dating. I am just rambling at this I point, but I do wonder if it could work because we are similar/get each other better or completely blow up because we are both too independent.
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