Lauren tells Ryan that the first birthday after a loss can be tricky, so the group wants to support him in the most awesome way possible. Yolanda has set up a scavenger hunt based on Ryan's life! Sadly, Ryan doesn't want to celebrate his birthday, so Lauren pulls out stuffed animals for a role-playing demonstration of Ryan's inner dialogue. Ryan grabs the animals to let everyone know that Janie used to go all-out for his birthday, planning way in advance, which he never liked. He's been looking forward to spending his birthday alone. And besides, he has to watch Steven, who's scheduled for a medical procedure that day. When registered nurse Sonia offers to watch Steven, Ryan caves to the group.
Steven is still looped on anesthesia when Ryan brings him home from his colonoscopy and launches into an emotional rendition of "Dust in the Wind." Sonia knocks on the door, upset by drama with her ex-boyfriend. Luckily, she's overjoyed at the prospect of Steven, now passed out. He's so pretty, Sonia just wants to pet him and brush his hair. Ryan warns her not to let Steven leave the house or buy anything, then heads off to join the scavenger hunt. The first stop is a dry cleaner where Ryan's team - Lauren, Anne and Mr. K - have to persuade the proprietor to put Ryan's headshot on his wall of fame. The other team isn't far behind. Just as Yolanda begs Ryan to be happy, he takes a scheduled call from Carrie. There's a "code black" at work, and Ryan's gotta go.
Lauren follows Ryan out the door to ask permission to speak outside her role as counselor. The group cares about him, and they're trying; and if he keeps pushing them away, they'll stop trying. Ryan explains that he acts like a spoiled little boy with the people he loves; Janie got it all the time. Being a jerk is a pre-existing condition for which there is no cure. Lauren advises there's a key to being a better person: fake it 'til you make it. Ryan decides to go for it and charges back into the dry cleaners to persuade the proprietor he's Rachel Maddow, claiming a spot for his headshot on the wall of fame.
Steven wakes up, feeling the urge to shop for pretty clothes. Lucky for him, Sonia is a pushover, and it's not long before he's giving her a fashion show in a pricy men's boutique. At one point, Steven has a moment of clarity: did he just spend $2,000 on cigarette pants!? Sonia explains her part. Steven is a pretty man, and while he was under the influence, he was a dumb pretty man, which is what she used to have with her ex. Now he's got photos of himself and his new, cute girlfriend plastered all over Facebook. How's she supposed to compete with that? Steven takes charge. They're going to dress Sonia up in booby shirts, take pictures and post them to make her ex jealous. Then they're going horseback riding - he's still high!
Having succeeded in their first task, Ryan's team moves on to the next one: recreating Ryan's act of streaking in college. Everyone looks at Mr. K, but before he can get naked, Danny (on the opposing team) runs by in the buff. Ever a joiner, Mr. K rips off his clothes and prances off, prompting Anne to remark he has moves like Gene Kelly. Next stop is K-BAL, where Ryan is upset to learn Carrie just gave away the T-shirt gun to the other team. Luckily, there's a spare, and in moments, the teams are facing off, shooting down life-size cutouts of Ryan. When Carrie announces there's a limo waiting downstairs, everyone thinks it's part of the scavenger hunt, arranged by Yolanda.
Ryan and the gang bump into a jazzily dressed Sonia and Steven on the street, and Ryan smells a rat right away. She wasn't supposed to let Steven out of the house! Sonia admits people trust her because she has a soft voice, but she's bad. Ryan loads everyone into the limo, then pauses to tell Lauren that truly, this is the first birthday he's enjoyed in years. Lauren climbs in the limo to find a hotel key card nestled in a champagne bucket. She quickly deduces the limo and hotel key are all part of Janie's advance planning of special birthdays. Fausta immediately cracks open the scotch as Ryan hops into the limo, thrilled to see the hotel key card, thinking the hotel is the next stop on the scavenger hunt.
When Ryan remarks that he hates limos - Janie always threatened to get one for his birthday - the gang laughs nervously. Sotto voce, Lauren lays out a plan: someone has to stall Ryan, so an advance team can check out the hotel room to see what they're dealing with. Steven knows the way to stall Ryan: get him talking about himself. Sonia lays the trap as the others scramble upstairs where there's more champagne, rose petals, opera and a romantic candlelit dinner for two. The only solution Lauren can come up with is pretending the room is part of the scavenger hunt. When Ryan finally makes it upstairs, he finds Lauren scooping rose petals off the bed. Did she send everyone away so she could seduce him?
Lauren claims Ryan's blinding self-confidence has led him to the right conclusion: this is a seduction. Ryan is just sensing something is wrong when the rest of the group files into the room. Lauren finally opts for the truth: Janie must have set up the hotel room birthday party before her death. Adding insult to injury, a violin player enters the room, which puts Anne in the mind of Cyd Charisse and Gene Kelly. She holds out her arms to Mr. K, and they perform a dramatic and sexy dance for the group. Pretty soon everyone's dancing.
Ryan heads out to the balcony, where he's surprised to find Janie waiting for him. She probably shouldn't have planned this birthday as early as she did, but she got a great discount. Ryan admits that this is the first birthday he's really enjoyed and didn't act like a whiny baby. He's becoming a better guy, and he wishes she were really there to experience it. She deserved better. Janie insists she loved the Ryan she got and advises him to head back to the party - no looking back.