system
A chat on subreddit /r/NoStupidQuestions
human
I understand feeling insulted. The wording very closely resembles the "You're pretty ____ for an _____" phrase. In this case, literally that you're pretty for a tall girl. It feels backhanded and I'd struggle to find it complimentary.

I agree with other comments here it might just be awkward wording, and possibly a way to make light of both your heights. But ultimately, badly worded comments can hurt, even if well intended, and it's valid to feel that way.

As for leaving the date? That's a judgement call. If it was just the one comment, I personally wouldn't (depending on severity). But I would also feel quite comfortable calling them out on their wording, to get to the root of what they mean (literally just "thanks I think, but that was an odd way to phrase it?"). Their response would tell me a lot. If there were multiple comments throughout the date, I'd leave, making it clear exactly why they bothered me and why I was leaving.

I appreciate that if you're not there yet, this could be quite a daunting thing to do - both calling them out, and actively leaving. Especially if you have had bad experiences with dates acting entitled to your time in the past, they can become quite nasty quite quickly. It's why, overall, I believe that first dates shouldn't commit you to long periods of time together. That way you can always make your excuses and leave after the next coffee or beer if things don't seem right or you simply don't click.
gpt
Yeah that’s how I felt the wording was even though I now see where everyone is coming from with the joke perspective. Next time I would definitely call it out to get more of a feel of what the intentions wrre