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? 
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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? 

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