That night, Jerry shows up at Milo's hotel room. Milo's dressed to the nines. Guess it was a formal affair after all.
Turns out that Milo lives in the hotel for most of the year. She goes home to Baltimore for Christmas and Thanksgiving, because Paris's got nothin' on Baltimore in the middle of winter.
It also turns out that Jerry's the only guest at Milo's party. That extra girl she told him about? It's her. Smooth, Milo.
Jerry's not having it. He gives Milo her money back, takes his paintings, and tells her that if she's that hard up for companionship, there are dudes in town who do that professionally.
Milo laughs and tells Jerry he has the wrong idea. She just likes his art and wants to get to know him better. Or so she says.
Milo continues praising Jerry's painting prowess and convinces him that it won't hurt to have somebody rooting for him. They decide to go out to dinner, as long as Jerry can pay.
Cut to a jazz club. Milo and Jerry get to know each other better. Her husband left her for another woman.
Jerry thinks she should get married again. Milo says she's got plenty of work to do; more specifically, she wants to sponsor him. She's a big art collector, and she's got fancy-pants art connections.
Jerry agrees to Milo being the Nike to his Michael Jordan, but he wants to know what's in it for her. She says it'll be exciting to help somebody she believes in, and she wants to see if she's right about him and his talent.
Proving Milo's point about her being a big deal, a guy named Tommy comes over and enlists Milo's help in showing around a couple of magazine illustrators who are in town visiting.
On the way to the illustrators' table, Jerry bumps into Lise, literally. His face says "love at first sight."
Jerry can't stop looking over at her, and he asks Tommy if he knows anything about her. Predictably, Tommy doesn't know jack about the random girl sitting at the next table, but Jerry manages to overhear that her name is Lise.
When everybody at Jerry's table gets up to dance except for Jerry, Jerry moves to the other side of the table so he can keep staring at Lise like a weirdo.
Meanwhile, on the dance floor, Tommy warns Milo that she needs to stop getting involved with young artists. It never works out for her. Milo tells Tommy to shut up and dance.
Back at the tables, all of Jerry's staring is making Lise visibly (and understandably) uncomfortable. Then Jerry approaches her table, pretending like he's an old friend, and drags her onto the dance floor with him against her will. Easy there, Captain Caveman.
As they dance, Jerry hits on Lise, and Lise is all, "What the heck was that?!" She explains that the only reason she didn't put up a fight when Jerry dance-abducted her is that she didn't want to make a big scene.
Meanwhile, as Jerry continues making Lise his dance hostage, Milo looks on. She's not happy.
Lise isn't happy, either. She wants to go back to her friends. Jerry won't let her.
Fortunately for Lise, the music stops.
Jerry escorts Lise back to her table and again pretends that they're old friends. When Jerry asks for her number so his "wife" can get in touch, Lise tries to give him a fake number, but one of her friends corrects her intentional mistake. Whoops.
Back at Jerry's table, Milo says she's going home. Jerry follows her, saying goodbye to Lise on his way out. Lise straight-up ignores him.
In the car, Jerry's in high sprits. Milo? Not so much. In fact, she's nearly in tears.
She chastises Jerry for trying to pick up another woman in front of her, and orders him to never do it again.
Jerry asks the driver to stop, and he leaves. We don't know about you, but we're starting to think Milo has designs on more than just Jerry's ability to wield a paintbrush.