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How to reapproach an old fling
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Hi everyone,

About a year ago, I met a 32F on Hinge in NYC (I'm 31M she's 33F now). I took her out on a date and we had a really great first date in Sept 2021. We were talking for a few weeks and at the time I was living with an ex gf and in process of moving out which I think pushed her away and ultimately poured cold water on whatever we had going. She also invited me to a festival in the city and I didn't go so I think that was the nail in the coffin when I declined. I have not spoken to her since. I've dated lots of women over the past year and to be truthful I think about this one often almost like the one that got away. It's the only one I've felt anything with. Yesterday I thought about her and I actually searched her on Instagram and somehow in gods name, found her. I was on the fence about adding her initially but after consulting my friend he said dude you mentioned this girl even after all this dating just add her and go for it. When I went to sleep last night I added her on IG, on the fence if she would accept me. I just woke up and she did in fact accept my request and, she requested me back too on IG, to which I accepted this morning. If I want to reapproach this woman to try and take her on a date again, any tips how I should do so without making it awkward? Is this a bad idea? She did add me back which is a little good sign. I don't know if she remembers me or not from my pics but I'm leaning towards the side she probably does. How do you not remember the face and name of someone you went on a date with? For the past year I've dated around a lot, slept with a few people and idk I just miss this one. I felt something there and I legitimately liked her a lot and I think for her it was going in that direction..and I basically never like anyone. any tips how I can successfully re-engage and talk to this one? I sort of wanna reach out to her and try, considering she's the one girl that I never really forgot about.

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2 years ago