Sounds like you are overthinking this. What's really going on? Does she make more money than you or have children? What does she dress like a classy woman and you're used to hoochie hoes? What's the reason for this thread? You just tell her you want to go out and to give you the digits. That's it.I think you're not understanding my point.
What I'm really asking about is how should I go about this, I'm not afraid of asking the woman it's more about when should I ask and how to go about it since she's older than me. If she was a woman in my age range (25-28) then I wouldn't have made this thread because I'd be right at home because of comfortability in talking with someone my age.
I don't usually mingle with women this older than me.
This woman is 33 and I'm 27. I've never dated a woman that older than me in her 30s. I'm trying to figure out how should I approach this, should I use my same technique or do I have to switch up because she's older and maybe even wiser than me?
Last edited: