Michael drives to a florist slash fancy restaurant as soulful indie piano music plays. Just as he's about to get into his car and go to town on his Bloomingdale's big brown bag of takeout, he runs into an old friend. "Anna?!" he says to Jennifer Ehle. "Michael!?" she replies. They fondly embrace, and she tells him how she moved to "his" city of eight million people, and he is just ecstatic to see her. He invites her back to his place, which is a truly amazing loft.
Apparently Anna was working at a dismal Inuit clinic in Alaska (presumably in one of those towns where you can only get to by one of three ways: by boat, by plane or by birth canal. I'll be here all week, folks), which she and Michael reminisce about while Michael plays the piano. Romance! She was recruited to a clinic in the Bronx, which is an un-glamorous as the Inuit place but not as cold. Michael's all, yeah, I left because I was cold haha, and Julia's all like dude, you left Alaska and me because you didn't want to be married anymore. He dodges the comment and asks her how long she's been in town... and it turns out she's been there eight years. She's lucky Michael isn't her Jewish mother, I'll tell you that much. He's a little upset, but their rapport is fine, and he says that when he got back, he realized he didn't want to not want to be married to her. She asks what he did in that near decade of being apart, and it turns out he didn't do much of anything, as far as the relationship department goes. And neither did she, because they are in LOVE. He tries to charm her with blah blah you're beautiful and she's all, "Play on, player. You're not getting under this oversized sweater." She's gotta run, but she thanks him for the wine and company and leaves. "I'm happy you're happy," she says on her way out. "Who says I'm happy?" replies the world's most pathetic billionaire doctor whose still in love with his awesome ex-wife. The phone rings and she's gone.
On the other line is a collect call from Michael's nephew Milo, who is at the 83rd Precinct over in Bushwick. He picks up the kid, who is an XXXtreme teen skater who just wants to chill with the "gang kids" in Bed-Stuy, but no dice. He drops him Milo off at home, where Michael goes in to talk to his sister Christina (Julie Benz) and her adorable dog. He lends his sis some much-needed cash that she reluctantly takes, and then tells her he had dinner with Anna. Christina is like, "ANNA PAUL?! GTFO!" but all Michael really does is tell her that she has to whip Milo into shape.