Bill enlists Alex's help in convincing a tavern owner to sell his building in order to secure the plans of their law firm's biggest client to build a skyscraper on and around that spot. Things become complicated for the normally unstoppable and all-business Alex when Scott, the tavern's new free-spirited owner, repeatedly refuses the offer while earnestly attempting to woo the secretly smitten Alex.

Alex feels both empowered by and guilty about deceiving Bill, who despises Scott for ruining a multi-million dollar deal for Bill's law firm by refusing to sell his tavern. Meanwhile, Alex is torn about how to respond when a Manhattan magazine wants to feature her in an article as one of the city's 10 most eligible professional singles.

Though she's initially content to overhear Scott call her his girlfriend, Alex soon finds herself unnerved by the sighing sound he makes each time he takes a drink. When Bill notices this quirk of Scott's, he tries to provoke a breakup by offering Scott several tins of salty cashews to get him to drink, and sigh, as much as possible. Though Alex decides to save the relationship by simply asking him to stop making that sound, she's driven even crazier when Scott mentions that she has a few bothersome traits as well.

Julian is peeved at Alex who has become absentminded about her plans with him since she started seeing Scott. Alex tries to make things right with Julian but he won't even take her calls after she forgets to meet him for brunch and then flakes on her promise to score him a table at a fancy restaurant.

Meanwhile, Scott can't wait for them to reconcile when Alex makes him watch a silly reality show with her that she used to watch with Julian.

When Scott resists setting up Molly with one of his single basketball buddies, Alex confides in Scott that Molly is just seeking a little "fun" to get her back into the game. However, Molly thinks her night of "fun" with Scott's friend was the result of their deep connection to one another. Meanwhile, Bill commissions Julian to paint a portrait of his wife's troublesome dog as a ruse to get Julian to dog-sit while Bill's wife is away.

Though Alex, a self-professed "control enthusiast" who has never liked celebrating her birthday attempts to embrace Scott's surprise plans for her, but her workaholic ways quickly turn the afternoon into a different kind of adventure. Meanwhile, Bill is peeved that it was his nemesis, Scott, who succeeded in getting Alex to finally acknowledge her birthday, especially since he'd just told Scott to respect Alex's wishes not to try to celebrate it.

Alex feels like she and Scott have reached a dating milestone when they go shopping to replace Scott's lumpy mattress. However, when she learns about the history of his sofa, she can't help but let her insecurities surface. Meanwhile, Bill repeatedly causes Stephen to miss out on a much anticipated blind date with a former Miss Pennsylvania.

When Alex finds out that Bill is only pretending to like Scott as a means of landing a new client, she retaliates by telling her father that she and Scott are getting married.

Though Bill initially refuses to allow Alex to bring Scott to a business dinner with a potential new client, he welcomes Scott with open arms after discovering that the potential client briefly ran into and bonded with Scott. As a result, Bill is forced to mask his horror when Alex and Scott spring their fake wedding plans on him at the dinner in front of the newly signed client. Meanwhile, in an effort to attract women as easily as Julian does, Stephen starts faking a British accent.

After Alex and her cousin's childhood rivalry resurfaces at the cousin's bachelorette party, Alex is especially eager to show off Scott at the wedding. Suspecting that Scott won't forego his phenomenal seats at the Yankees/Red Sox game to take part in Alex's petty ploy, she devises a lie to persuade him to join her. However, Scott concocts a self-serving fib of his own.

Alex is excited to meet Scott's closest friends until Julian plants the seed that their first impressions of her could ultimately make or break her relationship with Scott. After shocking the friends and Scott with her maniacally competitive behavior, Alex attempts to do what she can to win them over the next night. Meanwhile, Bill tries to manipulate Stephen into turning down a partner position at another firm without making him a counteroffer.

Alex alienates Scott's best friends from Montana with her overly competitive spirit; Stephen is offered a partnership with another law firm, but Bill tries to keep him from leaving.

Alex accidentally gets Scott kicked out of his apartment while he's in Montana visiting friends, and she fears that Scott will move in with her.