Yolanda has made everyone a mix CD, filled with music from artists that died too soon, in hopes of bringing some fresh tragedy to the group. When Yolanda turns on "Chantilly Lace," Fausta immediately asks why Owen is singing. Ryan's got his own fresh tragedy: the loss of Simone. When Sonia suggests Ryan needs a good breakup song, Mr. K gets busy, urging the group to join him in creating the perfect tune. On top of everything else, Ryan just received Janie's life insurance check, and he doesn't want to be alone with it over the weekend. Anne's planning a trip to the bookstore - too boring - but when Ryan learns Fausta is going to bingo at her church, he's in.
At the bookstore, Anne's taken aback when smokin' hot yet dumb Brittney, the register girl, flirtatiously offers her phone number. Meanwhile, Ryan joins Fausta and her buddies at the church for bingo and spiked horchata. At first Ryan refuses to play, explaining he used to be a bit compulsive with gambling in his younger years, but when Dorotea accuses him of losing his cojones, he antes up. It's not long before a pumped-up Ryan wins his first bingo game, and Fausta reminds him that winning feels good because for a brief moment in time, winning is all there is. Realizing that truth, Ryan climbs on board the gambling train.
Not wanting to spend the night at home alone, Ryan invites the group over for March Madness gambling. He tells them he learned a valuable lesson from Fausta - everything is better with gambling. Turns out, Fausta's golden rule is everything's better with alcohol, but whatever. It's not long before the group is totally into it - except for Owen, who despite his superior knowledge of basketball, is losing to the point where his name has become synonymous with losing. As the group descends into looking for random symbols of good luck based on wins, they discover that when Owen is spanked, winning ensues.
When Ryan insults a coach on air talking about betting spreads, Steven charges into the booth, upset Ryan's gambling again. Doesn't he remember what happened in college? Ryan protests, but Steven knows he's an addict, who promised Janie he'd never gamble again. On the way to a session, the group is stunned to spy Brittney dropping off a seemingly blissful Anne. Ryan quickly corrals Fausta, Sonia and Yolanda into a new gambling game. Since Owen sounds like The Big Bopper, everyone else will compete, trying to trick him into saying lines from "Chantilly Lace."
Anne rushes in late to the group meeting in a very good mood. It's not long before the group is talking about Brittney. Anne claims she hasn't noticed that Brittney's attractive, but one thing's for sure, she's very intelligent. Ryan offers to invite his good friend Stephen Hawking over for the evening's March Madness betting session so Brittney will have someone to talk to. Alarmed, Lauren perks up - gambling can lead them down a very dangerous path, as it did her own father. She makes everyone promise to stop gambling, but Ryan refuses, since he's killing The Big Bopper game as they speak.
March Madness continues. When the group shows up at his house, a distraught Ryan is in the midst of a losing streak. Luckily, his bookie Marty is on hand to phone in bets, and Ryan's got games going on three TVs and two laptops. When Anne and Brittney arrive, Ryan instantly decides Brittney's good luck, despite her super-dumbness. Upset, Danny sets out to prove he's the dumbest guy in the room, making Anne realize she's dating hot Danny. That's when Steven bursts in to announce he's closed out all of Ryan's accounts. Losing his final bet of the night, Ryan starts throwing remotes at all of his TVs.
The next day, Anne admits she broke up with bimbo Brittney after Ryan's party out of respect for her dead wife's memory. How could she stoop so low? But Lauren and the group assure her she's allowed to have fun and do what makes her feel good. Anne misses Brittney, so she takes Danny's advice and runs out to make up with her. That's when Lauren realizes Ryan's missing. Luckily, Mr. K has hacked everyone's phones with a tracking device, so he knows Ryan's located at a casino in Temecula. Since Steven cut off all of Ryan's accounts, he's using Janie's life insurance check to gamble.
Ready for some action, Lauren finds Ryan raking in the chips at a poker table. After urging the gamblers to walk away from the table to experience the jackpot of self-love, Lauren has to try another tactic learned from her gambling-addicted father. She's going to take away the thrill of winning by beating Ryan every time, and he better get ready to hit rock bottom. Meanwhile, Ann returns to the bookstore in hopes of winning Brittney back. Knowing she deserves to be with someone who's proud of her, Brittney says goodbye forever, just as another hot lady hits on Anne.
As predicted, Lauren wins everyone's money, and Ryan's down to the last of his chips. Knowing all his tells, Lauren quickly wins the last hand. Luckily, she's prepared to give Ryan back Janie's life insurance money as long as he stops gambling. The next day, Anne stops by to commiserate over the loss of Brittney and Simone. They agree it's going to be really hard to meet someone. When Anne decides they need a fresh start, Ryan gets an idea. Sitting outside, they tie their wedding rings to helium balloons and let them float away.