A disheveled Alex rushes off the elevator at noon, trying to tie his tie. Helen raises an eyebrow, so Alex explains that rather than a specific time, the cable company gave him a "window," then never showed. Therefore, they're going to have to watch the movie at Helen's place. Helen immediately starts worrying about boundaries; the reason it's fine to get together at Alex's? His apartment looks like the first one he ever had. It's like going on a date at Wendy's - nothing's gonna happen. When Alex fails to tie his tie, Helen takes over, allowing that the movie can proceed at her apartment - as long as there are rules. Alex asks for no superfluous talking or crunchy snacks - but Helen's more concerned about "funny stuff." There needs to be rules and enforcement. The trouble is neither of them is willing to be the enforcer.
Gregg and Dan argue over the copy machine. Dan will be damned if he's going to Gregg's book club, since there will be zero chance of getting laid. When he learns that it's an all-chick book club, he promises to consider it as a last resort. Hot hedge fund dude Andrew from upstairs approaches Emma's desk, so she tells Gregg to get lost. Emma tries flirting, but it's clearly not her forte. Later, Helen, Alex and Stephen escort client Gerald Unger from Northbridge Telecom out after a meeting. Newly divorced Gerald has an eye for Helen, and she flirts back hard. After he leaves, Stephen informs that Gerald's being courted by wily Ted Elliot from a rival firm. Stephen's strategy to retain Gerald? Helen takes him out to dinner and treats him to her teasy/flirty thing that seems to "put ribbons on his maypole." Helen's game but is immediately convinced that Alex doesn't like it.
Later, Helen offers to grab a drink before her meeting with Gerald, but Alex isn't up for it - he's going home to do real work while Helen's out showing her boobs to clients. Helen thinks he's jealous. At Hale Dayton, they do whatever's needed to keep clients; Helen's got game, and Alex doesn't. Alex rallies. He's got game. He got Helen into bed, didn't he? Helen maintains that the four glasses of wine were the MVPs of that game and climbs on the elevator. Stephen barges in to inform there's been a change of plans. Instead of an evening of innocent flirtation, Gerald prefers a gentleman's night out with recent fellow bachelor Alex.
Later Alex and Gerald talk business over an expensive steak and martini dinner. Finally, Gerald puts his foot down; he doesn't want business, he wants action. After all, they're two men on the prowl! Can Alex make that happen? Meanwhile, a grumpy working-late Helen consoles herself with a dinner of sushi and a lot of saki, which she offers Emma. Emma wants to know how to flirt, a propos of Andrew the hedge fund guy upstairs. She's been putting it out there and getting nothing back, so she must not be sending the right signals. Helen advises Emma to make Andrew feel attractive with little teasy compliments. In fact, they should go upstairs right now to say hello.
Back at the restaurant, Alex is trying and failing miserably to pick up women. As desperation sets in, he picks up the phone and calls Dan, who's in the car with Gregg, on their way to the lesbian book club meeting. Dan promises he'll be there in half an hour with some babes. Threatening to drive the car into the river, Gregg manages to persuade Dan to let him tag along. Sadly, a half hour's too long, as poacher Ted Elliot shows up at the restaurant with his attractive colleague Patricia. When Gerald gets bored with Alex, he should feel free to join them. That's when Gregg and Dan show up with Catherine and Daneel, who look like they're barely legal and immediately start doing shots, toasting Harry Potter.
Meanwhile, security guard Walter intercepts Emma and Helen on their flirting mission, then decides to tag along. Emma's so bad at flirting that she gets right to the point, asking Andrew if he wants to get a drink. That's when she spots a Spin Doctors CD on his desk. Nauseated, Emma verbally assaults the Spin Doctors so badly that Helen hops in, turning on the flirt in an attempt to save the day. When Andrew points out that at least Helen's nice, Emma throws in the towel. It's time to go get a drink. Which is exactly what Alex is doing at the bar, attempting to hang on to Gerald, after Dan and his girls have ditched them. He's so desperate, he doesn't realize it when an attractive woman, Susan, starts flirting with him at the bar. When she tells him that flirting is what she's doing, Alex hopes beyond hope that his night is finally turning around.
A little later, Emma and Helen show up at the restaurant where Alex and Gerald are entertaining Susan and her friend Kara. Fully intending to make fun of Alex, then save the day, Helen's a little put off to discover that Alex is actually holding his own. She's just conceding victory, when Susan insists it's time to get business out of the way; she and Kara are usually paid up front. Alex tries to save face, but when Helen laughs at the suggestion of a five-way, the hookers huff off. Gerald huffs off to get the check and bumps into Emma at the bar. Luckily, Emma is in full flirt mode and mocks Gerald viciously. He's an idiot if he leaves Hale Dayton, since they're the only PR firm with the resources to handle his business. Alex and Helen just sit back and admire Emma's prowess.