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Dating : Should I try reconnect with an old tinder date after seeing her very randomly?

Dating : Should I try reconnect with an old tinder date after seeing her very randomly?


A few months ago I met a girl on tinder, we spoke for a while and arranged to go on a date. She cancelled a couple of days before it saying she wasn’t sure if she was ready as she had just broken up with an ex two months prior. I was cool with that and left her to it.

She got back in touch a few days later and after a few more days talking, she asked me if I was still up for the date. We met up and the date went really well. We arranged another date for the following weekend and spent the next week chatting. More often than not she would be starting the conversations and we were planning/discussing the date right up until the night before. She even reminded me to book tickets for mini golf the night before which weren’t super expensive but not cheap either. Then I wake up to a text saying she had to cancel to go into work. I was cool with it and we messaged a few times. Later that day i asked if she wanted to rearrange and she said she didnt as she wasn’t free for the next week with work (I work 9-5 and she often worked evenings so this could well have been the case) and then was visiting family for another week and wasn’t sure if she was « interested enough » to keep it up through text. I agreed this was a little much and again I basically said it was fine and we stop talking.

Fast forward 2 months and I’m on a family day out in a random small town and I see her out with her family too. Pretty sure she saw me too but at different times so we didn’t make eye contact. This isn’t a hugely popular town and is like 30 miles from where both of us live. It was also a weekday so not as many people visiting – basically a huge coincidence. It’ll now be 5 months since her breakup and I’m wondering whether it might be worth messaging her again? Don’t want to come across as desperate or the guy who can’t take a hint and I’m not one to see such things as « signs » but it has me curious. I don’t really see what I could lose by dropping her a message. What do you think? Also what would you message her saying?

What do you think?

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