The narrative begins with Andrew "Coop" Cooper on a well-deserved vacation with Mel, Tori, and Hunter. However, the kids are too engrossed in their own world to accompany him for their dinner reservation. Mel, who isn't particularly keen on returning home, jokes with Coop about lowering their expectations for future vacations. They reflect on the dramatic events from Season 1 and eventually knock back drinks, laughing about a girl at the bar who seems to be interested in Coop.
Mel eventually leaves, believing she's "cockblocking" him, but Coop takes it in stride. After all, going on vacation with his ex-wife and kids, when he was facing up to 25 years in prison, is the best-case scenario here! It turns out that Coop has fully embraced his criminal past and made a pretty penny from it. He's spending more time making amends with the kids, sleeping with random women, and even pretending to have his own office to make everything look legitimate. Things are on the upswing, and Coop is starting to feel quite optimistic.
As for Sam Levitt, she's gotten off easy with community service and a hefty fine after the murder. Now working as a realtor, she's faced with a charming billionaire neighbor who disrupts Westmont Village and changes the entire dynamic. Enter Owen Ashe. He immediately turns down Sam's house, pointing out all its flaws without realizing it's actually her abode. The pair talk about her husband's death before Sam points out that her house is being used as a "fluffer" to make the next house look much grander by comparison.
Ashe fires his current realtor, Reenie, and decides to bring Sam onboard instead. It doesn't take long before he's shown a new house and buys it, which means Sam will make quite a big commission chunk off this deal.
As Coop sets out on his nightly foray, he attempts to make off with a lavish fountain pen. Unfortunately, his back gives out, leaving Elena to rush in and offer assistance. Struggling to lift him, they are forced to enlist Barney's aid. Coop is compelled to reveal the truth as they make their way back to his abode, leaving Barney understandably stunned.
Barney endeavors to come to grips with this revelation, realizing that the art thugs from Season 1 are connected to this incident. These are the same individuals who ran over Barney, of course.
Meanwhile, Tori is conducting her interview at Princeton with Jeff Pratt, delivering a monologue about the system and how it is working in the rich's favor. She knows that regardless of what she says here, she's getting into Princeton.
Returning to Barney, his work is in a precarious position. He's relying on too few clients to prop up his bottom line, but Barney is confident that he can see this through. He speaks with Grace's father, bringing up how the art of wealth management comes from choosing clients like stocks.
Interestingly, Grace's father actually offers him an alternate job. It certainly gets Barney thinking and he winds up distracted that night when Grace tries to get busy. He struggles to get an erection and eventually admits that he's not happy about Grace setting up this meeting with her father.
That night, things take a surprising turn when Barney learns that Grace is pregnant. He's shocked but also very happy.
Elsewhere, Mel engages in conversation with Ali, who admits she's starting menopause and is conflicted because while she thinks she's getting uglier, she believes Coop is getting better looking. She also offers Ali a good gig working as an interim music teacher at Mayfield.
That evening, Owen Ashe threw a lavish welcome party at his newly acquired mansion. Sam soon arrived, but she felt uneasy mingling with the group of unfriendly girls. As she was about to leave, she collided with Coop, creating an awkward moment that fortunately passed quickly. Once inside, he struck up a conversation with Ashe, and the two of them displayed an undeniable chemistry. He also managed to win over both Nick and Barney, who were initially skeptical.
As the party progressed, Coop took the opportunity to explore Ashe's luxurious possessions while most of the guests were outside enjoying themselves. When the commotion died down, Barney and Coop engaged in a heart-to-heart conversation about Coop's decision to leave his previous job. He admitted that he wasn't happy with his life, but as they talked, Barney expressed his desire to join the operation now that Grace is pregnant.
