Found an old colleague on a dating app who I want to date. Do I tell them right away or wait until in-person?
I (M36) saw an old colleague of mine (F30) on a dating app the other day and I deliberately did not match with them because I thought it would be weird. We used to work in the same office around 4-ish years ago and I've always had a thing for her, but I was in a committed relationship with another woman at the time. Now that I'm single and dating I started thinking about her in the context of old crushes I used to have and then, amazingly and out of the blue, she popped up on the dating app I was on the other day. I have her cell number from the time when we used to work together, so I went ahead and texted her to see if we could catch up sometime soon. She said yes, but I didn't mention the dating app sighting, nor did I mention that I'm single yet. As of right now I'm pretty sure she just thinks this is a friendly catch-up session with an old work colleague. I don't want to creep her out when I go see her in person to catch-up, but I also don't want to withhold the fact that a) I saw her profile on the dating app, b) I'm now single, c) I have always been attracted to her, and d) I would like to ask her out. How do I talk to her about all items a-d in that list without coming across like a creep and messing this whole thing up? Do I call her before we have our catch-up meeting? Do I text her this info before we meet? Do I wait until we're together in-person to tell her all these things? Do I even tell her the first time we meet or do I wait until after we see each other to lighten the shock? What's the best approach? Thanks everyone.