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I am 47 he is 21. He had been dating a girl about 7 years older than himself. 2 weeks ago he told me he was thinking about breaking up with her. He asked me if the guy I was dating was casual. Last week when I saw him the first thing he told me was that they broke up. We talked for quite awhile. We always do. We have a lot in common. He also told me he was talking to another girl though. This is all complicated by the fact that I am friends with his family. I have only known them for about a year and a half though so it’s not like I knew him as a teen or anything. When we first met we hit it off immediately but I didn’t think anything of it, though I did catch him checking me out once. Then his mom told me he had a “crush” on me That he talked about me at home all the time. But I as I have gotten to know him I think maybe he just enjoys talking and flirting. sometimes we text. Not sure where to go from here. Maybe there isn’t even anything there and I am just imagining it?

ETA: Update: I think this will most likely be a friendship only. He seems pretty into the new girl already and I think any attraction he might have to me is overshadowed by the age gap.

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1 year ago