system
disappointed: I didn't ask the girl I like to the Prom and I really wish I had.
human
I didn't ask the girl I like to the Prom and I really wish I had just gone for it.
gpt
What was holding you back?
human
Well, I felt inadequate because it was summer school prom and she didn't have to go to summer school.  I thought it would make me look stupid.
gpt
If you could do it all over again, how would you overcome , and pardon me for saying this, your wimpy-ness?