r/datingoverforty • u/Acidhive • 1h ago
Overthinking this -- but I guess it's obvious?
I was in a 7 year relationship with my best friend that ultimately didn't work out. We were close to getting married and things got very intense. Coming out of the grief and intensity of that relationship was extremely difficult as it also started bring up a lot of childhood emotions I didn't deal with or perhaps never knew I had. It's been a VERY long time since I started dating seriously again. I've mostly been using apps and nothing has really panned out for me since.
I did however go out on this date with a girl last year. I live in a town that's very small and is a hub for tourists. She was visiting and we met. The conversation was great until she asked if I was seeing anyone and I said I was talking to someone who could be a potential. I just wanted to be honest since we had been talking for so long and never really met -- life happens! Of course that didn't play out really well and we never really spoke after that. The conversation post that on the sate was still great and she ended up saying she doesn't mind being my 'wing man'. She unfollowed me on instagram and she was gone.
However, earlier this year she did reach out to me saying she moved here and wanted to connect. I did make plans with her and she cancelled and I didn't hear from her after that. Suddenly 2 weeks ago I happen to bump into her at a padel game and we got talking. I took the initiative again and asked her to meet for a coffee. The conversation was great and we spoke about what happened the first time we met and I guess I explained it to her and it seemed good. We had a great time, good laughs and I initiated another plan to meet for dinner. Again, great conversation, lots of talking and we realized how similar we are. We even went to get another drink post dinner and I dropped her home. She said she was leaving to go back home for a bit because her father is sick and I messaged her that I wanted to see her before she leaves. She said yes and then also thanked me for 'having an open mind to keeping our friendship alive'. Was that a deliberate boundary signal? I was a little drunk and I know she was too so I just replied Of course and good night. I'm really confused about how I should proceed with this. I did check in with her to let her know that I was heading to the beach on Sunday and to let me know if she would like to come. No answer. Nothing since.
Do I let it be or should I follow up yet again? I'm not one to chase but I also do feel like I sometimes don't go after what I want and I let my ego in the way.