I'm 36M. She's 27F. Want to be more than friends, but HOW? Never been in a relationship. Don't know what to actually do? or how the process looks. Help?

I just met this pretty cool girl (26f) at work a few weeks ago. Our schedules vary so we don't always work together or when we do, we don't have enough time to talk. But the times that we have been able to talk, she's pretty damn cool. I like her far more now that I'm slowly getting to know her.

I think my chances are extremely slow because I'm 9 years older than her, but I want to try. But I don't know how the whole process works or how it looks. It's making me stress out just thinking about it. I really don't know.

I've never had a gf. I have asked women out before but nothing really worked out. Been only on a couple of dates. It's been over 5 years since I last asked a woman out though. I don't know at what point one asks the girl out. How much getting to know each other, etc. I don't want to directly ask if she's single because it might show her I'm interested too quickly or something. I don't know what signs or body language a woman may show if she's interested in someone.

I'm already thinking I will fail because of my past experiences... lack of experiences. But I still want to give it a try. I'm trying to get as much advice as possible. Dating isn't something they teach you in school. I never learned it. I have always been scared and it was only until my early 20s when I challenged myself to ask women out and stuff.

Posted Dec 3, 2025, 1:29 AM UTC

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