Uncle Jack: But Valentine’s Day is here, and I’m alone. Perhaps if I had a little companionship, I’d be a little more disposed to whip out that old wallet of mine.
Michael: You’re saying if-if I were to set you up with my sister, you would consider bailing us out?
Uncle Jack: Oh, yeah.
Ready, Aim, Marry Me! - 2x10
Ok, we know they didn’t meet in the show, but just pretend this conversation is happening before Jon Arryn’s death, mmkay?