That's kinda funny actually, although kinda sleazy.

I wonder if the staff managed to hint to the dates that he's a regular.

I had a boss do this. It was a little awkward because I couldn't figure out why. There were several groups and we were a couple of minutes in before I figured out that they'd just been going to the same puzzle with different groups.

I still don't know what that was about, but it made me forget about the room entirely and try to figure out why you'd go through the same one more than once (it wasn't super interesting, but there were a few neat parts). Another guy just asked for a hint whenever the bosses didn't respond and that was pretty good.

As much as I like escape rooms, I'd definitely reject the idea of having a first date with a man be somewhere where I'm locked in with him for at least x amount of time and I'm being judged on my actions. All I would be thinking about is "get me out of here!"

I know there are people monitoring the situation but I still would never agree to be so dependent on strangers on a first date.

Maybe go to a board game cafe instead and play some skill based games?

This is a strategy Dennis shares with Charlie who tries it then forgets a step and proceeds to lose his shit and goes nuts trying to escape.

I think video games are a great way to get an idea of compatibility. I like Resident Evil 5 to gauge compatibility. I know it sounds silly but my ex-fiance was not a gamer yet we beat the game on the highest difficultly. We also had an easy time with Army of Two. The ex I had last, whom was a gamer, it was a thorough struggle. It's fun to see how well you work together even if it's a game.