I (28M) hung out with someone (28F) 9 or 10 times a few months ago and things didn’t work out for either of us.

I think it was circumstantial more than anything else. She was overworked and didn’t have a lot of time, and recently out of an abusive relationship, and I had been dealing with some fairly debilitating, grief-related depression.

We had good chemistry together but ended things mutually (and on good terms) due to the above. We haven’t talked since but are connected on socials, etc.

I’ve casually dated but haven’t really met anyone I’ve liked much since she was around.

I want to see what she’s up to. My life hasn’t changed much, I don’t know about hers.

However, I can’t help but think that I might not be doing myself any good.

Is sending a ‘hey, I want to see you again’ ever a good, worthwhile or successful thing, from any of your experiences?