Somewhat paraphrased translation - omiai can be a blind date, but also an arranged marriage interview:
Man, being set up with someone is so troublesome…
Asuma-san, Hatake-jonin. Welcome back!
Ah, Iruka! we drinking tonight?
If it’s Asuma-san’s treat, we can go anytime! Sorry, I have to go now!
… how do you know him?
He is something like a little brother, heh.
Getting set up…
Set me up with him now!!