I [M 31] think I don’t know how to/ am terrible at flirting on dates. When I meet a woman I’m really interested in, it seems like we have 1-3 really great dates and then I get a “let’s just be friends” text. Looking back on these past dating situations, I remember having good chemistry with each person and we had great conversations. But I always struggle to translate that into being flirty and expressing my interest in them because I don’t want to say something dumb or inappropriate or anything that would make them not want to date me. Basically, I’m so worried about someone not wanting to date me because of my bad flirting that I don’t flirt so they don’t want to date me. I feel like I’m not allowing the relationship to get off the ground because of it.

This happened to me again this last week and it was definitely the toughest to deal with yet. It was only two dates, but we had such a great connection and really deep conversations about who we are as people. We laughed and talked about our shared interests. We talked about the future and the kind of families we want to build. We both shared things we don’t normally talk about. I was so excited I told friends about her and everything. But when I tried to make plans for another date, I got THE TEXT. I feel like this happened because I was not able to flirt with her enough/at all and an amazing opportunity slipped through my fingers. I really want to make this the last time that happens to me.

So my question is, what do I do? Just go for it and hope for the best? What constitutes a flirt? Has anyone else faced this and gotten over the hump? Are there such a thing as “how to be a flirty, irresistible hunk” lessons I can take? I will take any suggestions on anything, I’m at a loss. Going on a few dates with someone and not having things work out is all part of the process of dating, but I’m struggling with the idea I keep failing for the same reason and I don’t know what the solution is.

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