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I l am 29/M. I met a 45 year old woman online a couple years ago for a drink. She thought I was too young for her after our first date so there wasn’t a second date.
A couple weeks ago I hit her up to see how she was doing. We started talking and we were going to boating on a lake instead. It rained today so we decided on dinner tomorrow night instead.
She insists it’s not a date but she’s letting me pick her up etc.
Planning on bringing her a bottle of wine when i pick her up, invite myself in when I drop her off and try to escalate.
As far as a plan, that’s all I have lol. It’s worked in the past and hasn’t worked in the past.
I l am 29/M. I met a 45 year old woman online a couple years ago for a drink. She thought I was too young for her after our first date so there wasn’t a second date.
A couple weeks ago I hit her up to see how she was doing. We started talking and we were going to boating on a lake instead. It rained today so we decided on dinner tomorrow night instead.
She insists it’s not a date but she’s letting me pick her up etc.
Planning on bringing her a bottle of wine when i pick her up, invite myself in when I drop her off and try to escalate.
As far as a plan, that’s all I have lol. It’s worked in the past and hasn’t worked in the past.
Any other tips?
Tips? Be a gentleman. Don't ask her to split the bill.
Just go, treat her like a person and not a blow-up doll, and have a good night. Things might end up the way you want anyway if you behave like a human and not a heat-seeking missile.
This. This is basically your first date with her, and you're planning to get her soused, push your way into her place after dinner, and use her to end your dry spell? On this "not a date"? Oh, but I guess with the age difference, you're not expecting there to be anything serious with her, anyway? No wonder she thought you were too young, the earlier time.
She wasn't into you a few years ago - so she probably isn't into you now. This won't be a good ending.
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