Question about establishing romantic intentions and progressing from "just getting coffee" to first date

I [28M] recently reached out to someone [28F] I was involved with in college. We haven't spoken since college (no hard feelings, just kinda drifted apart), so while it took her by surprise, we were quickly back to joking around and doing what little catching up we could do via text. I asked if she wanted to meet up for coffee so we could actually catch up and she agreed.

I have a pretty good feeling that this could progress to reestablishing romantic intentions, but it's been a while since I've dated and I don't want to botch the execution. I'm wondering how to proceed if the coffee "date" (not really a date) goes well. Should I ask her on a real date then and there? Should I let some time pass and proposition her later via text? Should I not ask for a date at all and just ask when I could see her again? If so, when should I communicate romantic intent and how?

I'm a big overthinker and I don't have a keen dating instinct, so even though the answers to my questions are all probably "feel it out," any insight into that process would be appreciated.



Submitted November 24, 2021 at 01:10AM

I [28M] recently reached out to someone [28F] I was involved with in college. We haven't spoken since college (no hard feelings, just kinda drifted apart), so while it took her by surprise, we were quickly back to joking around and doing what little catching up we could do via text. I asked if she wanted to meet up for coffee so we could actually catch up and she agreed.I have a pretty good feeling that this could progress to reestablishing romantic intentions, but it's been a while since I've dated and I don't want to botch the execution. I'm wondering how to proceed if the coffee "date" (not really a date) goes well. Should I ask her on a real date then and there? Should I let some time pass and proposition her later via text? Should I not ask for a date at all and just ask when I could see her again? If so, when should I communicate romantic intent and how?I'm a big overthinker and I don't have a keen dating instinct, so even though the answers to my questions are all probably "feel it out," any insight into that process would be appreciated.
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