We poked fun at each other a lot on our first/second date. We’re about to have our third date. She told me she’s very ambitious and goal-oriented (she’s a very successfully businesswoman). Would it be rude to text her “I hope you’ve had a productive week (include briefcase and suit/tie emoji)”. It’s poking fun at her intense business drive, but I also don’t want to make it seem like I’m judging her character or who she is in a negative way (I like her just the way she is).

Thanks in advance!

4 comments
  1. Sounds fine since it’s a borderline compliment. And the general rule is that it’s safe to gently tease people about their strengths, but not their weaknesses.

  2. Throw in a joke at your own expense there to make sure this is taken the way you want it to

  3. You can always go with the uplift-complement combo. Send the emoji or a pic of yourself dressed in suit and tie. Text ‘I found your passion for your career inspiring this week. Hope your week was great as well’

    Everyone loves to feel like they made someone happy.

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