Me 28 y/o, her 30 y/o. Both career people in high end professions. We met through work although we don’t work together. It’s a Tuesday and I don’t have anything else planned for the night so I decide to text her to setup our first date. I choose a bar close to her apartment (logistics). I ask her to wear something girly and to meet there at 9pm.

I arrive 10 minutes late, and she’s already there. Make-up, tight dress, and heels. I actually didn’t recognize her at first because her work demeanor / dress is much more masculine.

We sit down at the bar and start chatting over drinks. She’s doing almost all of the talking. I’m nodding, keeping eye contact with her, and escalating till I’m squeezing her thigh. I’m getting bored so I let her know I want to leave and walk around the venue. “Are you going to pay for my drink?” I joke. To my surprise she picks up the tab gladly. We exit the bar into the warm summer breeze.

No real shit tests so far, just lots of personal questions, trying to figure me out. She really wanted to know my age but I wouldn’t give her a direct answer, saying things like “younger than you” with a smirk. We find a secluded park, sit down, and start making out. I know she’s into Game of Thrones, so I suggest we go back to her place to watch. She protests a little, saying she needs to get up early for work and we should do it another day. I figured she was bluffing, so I persisted. Next thing, we’re driving back to her place.

I feel pretty good about my handling of the date so far. After a brief apartment tour, we’re on her couch. We make out some more, fondling, I’m whispering dirty things to her, etc. but whenever I move to take her clothes of she stops me. I back off, direct my attention elsewhere and try again after a bit. We repeat this maybe, four or five times over about an hour.

At this point, she tells me “everything in my body is telling me yes”. However, she’s come to think sex is the most superficial part of relationships, and that she’s trying to get away from one-stands and move her love life in a different direction. Says she’s been “a good girl” for the last year. She goes to change into her PJs. At this point its about 1 am and I know she needs to get up early for work. I interpret this as her way of saying, it’s time for me to leave, although she has not explicitly told me to. She kisses me goodnight and I drive home.

My specific questions are:

  1. Should I have stayed longer and pushed harder through the LMR? I feel like I went as far as I could but maybe I’m wrong.
  2. Do you think her good girl rebranding was legit, or a shit test?

Thoughts are appreciated