When I was in yeshiva, there was an alteh bochur who got very nervous on dates.
So what we did for him, is we would script his entire date for him. It took a lot of research into the girls he was dating, so like if we’d have him ask where she went to seminary, we had to have the right follow up questions for him (e.g. where’d you to to seminary? Bnos Sarah. Oh, that’s the closest one to the dining room, right? No. Oops, must have read that on YWN. You read YWN? No, my friend does and tells me what it says. Whose your friend? PBA. Phew! At least I know I’m not dating him. Of course you’re not dating him, you’re fat (PBA-we had to know if she was fat). Slap.).
Over time, we got better at predicting what girls answer to questions, so we had much less of those awkward moments where she’d go off-script and then he’d have to just stay on script and the conversation sounded all weird.
I’d be happy to write a script for you, if you’d like.