I l am 29/M. I met a cougar 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?