Chelsea Piers. Gavin and Henry are driving golf balls as Gavin says he bought the Drake in '86 and it's doubled in value a dozen times. Jeezy creezy. Gavin compliments Henry's swing and asks if he ever plays for money. Henry says he's not a gambler, but Gavin says moving to New York shows ambition, and with ambition there's risk. "So I'm gambling with my life?" Henry asks. "Always," Gavin says. Um, sure, dude.
Jane comes back to her place to find Olivia posing in the dining room. Egad. She says the door was open and she's here to take Jane dress shopping. Jane protests that she was going to the library, but Olivia steamrolls over her and orders her to try and transform herself into something less resembling a grubby ragamuffin, and quick.
Gavin introduces Henry to Daniel Stone, who gripes at him for offering a short sale on one of his properties. Or something. People talk real estate and leverage and giant sums of money and to me it just sounds like the teacher in Charlie Brown. Gavin exposits that Daniel is having some financial trouble and he can help, but Daniel says he'd rather go bankrupt than sell to Gavin. Gavin's like, be my guest. Daniel tells Henry he seems nice, and should keep better company. Henry asks if Daniel was talking about the "Greenpoint Towers complex." Gavin confirms, and Henry reminds him that he works in city planning, and that they're in a legal dispute with that building, and therefore it's borderline illegal for Henry to have contact with Daniel. Gavin apologizes, and Henry brushes it off and says, "You didn't know." He turns back to his ball and Gavin smiles, because of course he knew.
Dress shop. Jane has been eyeing a dramatic red McQueen. Olivia remarks that red was her daughter Sasha's favorite color. She died in a car accident a long time ago, Olivia says. Jane gets a case of the awkwards, but then Olivia insists she try the red dress on. In the dressing room, she looks at the price tag and has a small aneurysm because it costs more than my first car. She comes out of the dressing room and tells Olivia this place is just too rich for her blood, and Olivia brushes her off, insisting on paying. Jane says she just can't, and Olivia gets snippy and offended and rushes off to another appointment.