[gpgn]

How does that work in dating? If you are afraid of making people uncomfortable by asking them out, escalating things and putting them in situations where they have to say no to you, you may just end up being single for life.

[reg_dunlop]

Not at all related to dating, but this makes me think of the Curb Your Enthusiasm scene where Larry David's mother died while he was in New York on vacation and his father didn't want to "inconvenience" Larry out of respect for her dying wishes: "don't bother Larry".

Great scene and tangentially related to your premise.

[jzb]

Clearly that isn’t the case, given that ask culture has perpetuated itself.

Something like this: “I was thinking of seeing New Movie” “Oh, I’ve been wanting to see that” “I’m going Friday after work. You could join me if that sounds good.” “I’d like that!”

It’s not hard. You establish if someone is open to a date and it’s okay to ask if you’re getting the encouragement to do so. If you’re not, you drop it and save both parties the awkwardness of saying no.