It's lunchtime and Carrie is eating a take-out salad at her desk while watching a "Real Housewives" show. Ryan stops by and cracks a joke, but Carrie knows the truth: deep down inside, Ryan loves girl stuff. He admits it's true. When he was married he had a free pass to fun music and pink drinks because his wife was "forcing him." As proof he offers his "real" iPod, which is packed with Katy Perry songs. Softening, Carrie invites Ryan to be her girlfriend, thus beginning weeks of watching reality TV with Chablis, jewelry-making and Zumba.
To start the new year off right, Yolanda brings Japanese goal-setting dolls sent by her grandmother in Tokyo to the group. Her grandmother has already written goals on the bottom like "be taller," "find a man" and "don't suck." Yolanda allows that one of her dolls helped her to get a better job. Starting tomorrow, she's head of anesthesiology at St. Michael's, which is where Sonia works. Yolanda's hoping she'll finally have a friend at work, but Sonia's not too sure; her cool bar is pretty high. Ryan misses being out with a woman. He's been hanging out a lot with Carrie, but it's time for him to go on a first date. Unfortunately, he feels as nervous as he did in junior high. Laura assures Ryan it's just a question of finding the right woman. After some discussion, the group decides Ryan should find a funnier Rachel McAdams with bigger boobs, which he promptly writes on the bottom of his goal doll.
Later at work, Ryan is interviewing Olympic snowboard medalist Shaun White when he spots a superhot chick outside the booth. Ryan starts stuttering, as does Shaun, but his sexy hair flip draws the lovely lady's eye. After the show, Ryan explains his goal doll situation, asking Shaun not to pursue the hottie - there's no way Ryan can compete with Shaun's hair flip. Carrie walks up to introduce the hottie, her friend Hannah. Ryan is wildly awkward, and Shaun can't help flipping his hair - at both Ryan and Hannah.
Later, Ryan asks Carrie if Hannah was into him. Carrie explains Hannah makes everyone feel that way, which is how she gets everything she wants. When Steven accuses Carrie of being catty, she counters. It's complicated, and Hannah wins at everything. Okay, maybe she's a little jealous, but Ryan should consider himself warned. When his heart's broken, Carrie will be on call with sad girl music and ice cream. Yolanda meets Sonia at the cafeteria at work. She's nervous, afraid she'll be pigeonholed once again as a stick-in-the-mud. Luckily, Sonia has just the ticket. They're going to recreate Yolanda as a "slutty party girl." Sonia wastes no time getting started with the handsome Dr. Grimes.
Ryan takes Hannah to dinner, and it's not long before she's asking if he's okay. Ryan admits he's nervous, which means he's going to spill things and try to seem smart, which Hannah finds cute. She leans over and gives him a kiss, causing Ryan to dump wine on his pants. Later, he tells the group that he colored an eye onto his goal doll. Laura is incensed to learn Sonia is crediting Ryan's goal doll for his success, and Yolanda thinks her goal doll is making her popular as a slutty party girl around the hospital. Danny runs in excitedly. He finally stood up to his wife's boyfriend, and he owes it all to Lauren... who introduced him to Yolanda who gave him a goal doll. Pretty soon everyone's drumming on their knees and chanting about their goal dolls.
The next day at work, Ryan and Steven are in tuxes preparing to go to a fancy broadcaster's dinner when Ryan receives a breakup text. Ryan complains that he can't face the party alone, so Carrie offers to go. Later, Lauren finds Mr. K sitting alone in the group therapy room. Apparently, the rest of the group decided to take the day off to celebrate goal achievement. When Ryan walks in wearing his tux, Mr. K thinks it's costume day and runs off. Ryan tells Lauren that Hannah broke up with him, and now Carrie is his pity date to the fancy dinner. Strangely, he doesn't feel that bad. Maybe Lauren is right - Ryan's built up some emotional armor and has no fear. At least he has no fear until Mr. K runs in wearing naval dress whites to scoop Ryan into his arms and declare, "We're all thinking 'Officer and a Gentleman.' Let's do this!"
Ryan proceeds to the restaurant where he knows Hannah is having a dinner date with Shaun White. Even though Shaun is cool, Ryan has decided not to accept Hannah's text, because he and Hannah have something special. Everyone can feel it, even Shaun. Shaun is impressed that Ryan's going up against him and so is Hannah, who puts down her napkin and leaves with him. Meanwhile, Yolanda is rocking her slutty party girl persona at work with Sonia... until she's approached by a guy from HR, who's concerned about her health and competence. Yolanda is to report to his office for a drug test, but Sonia tells her to refuse or risk ruining her new reputation. That's when good girl Yolanda runs off begging for her job.
Ryan proceeds to the fancy dinner in fearless mode, full-out flirting with Hannah and fully forgetting that he asked Carrie to be his date. Thrilled when Steven's date calls her a skank, Carrie hurries over to tell Ryan at the bar - which is when Hannah sidles up. Ryan tells Carrie she can hang out and assist, but clearly that's not going to be any fun. The next day, Ryan crows about his newfound fearless persona to the group, claiming Lauren deserves all the credit. When he shows her a photo of how beautiful he was, all she can see is a dejected Carrie feeling badly in the background. The group can't believe Ryan forgot to cancel his date with Carrie. He's got to be more careful that his emotional armor doesn't make him numb to the feelings of others.
Yolanda and Sonia walk in to the session late, in mid-argument. Sonia wants to mourn the passing of a friend, Cool Yolanda, whom Yolanda murdered. Lauren nearly murders her gong to make the point that none of them have to worry about being cool. They're all perfect just the way they are. Sonia is going to accept Yolanda for who she is, and Ryan is going to make things right with Carrie. To prove her point, Lauren high-kicks Danny's goal doll to kingdom come.
Carrie's at home eating chocolates and watching "Real Housewives" when Ryan knocks on the door with a heartfelt apology. Carrie is a special person to him and from now on, he's going to treat her that way. And he brought her the expensive hot pink snuggle slippers she wanted to seal the deal. It's a good start, but not enough. Ryan owes Carrie a good night, so he's going to have to put on a tux. Tonight. Later, Ryan's at home putting on his tux when Hannah knocks on the door. She did get his text cancelling their date, but she's not accepting it. She's flying to Milan for a new job in a couple of hours and she'd like to spend those hours in bed with Ryan...
Not much later that night, Ryan finds himself sitting on the couch with Carrie, eating ice cream and watching "Real Housewives." When she learns Ryan chose her over Hannah, she has to admit it feels good. In fact, Carrie was feeling so competitive with Hannah that she thought she had feelings for Ryan. And how could that be? Ryan's so old! Carrie wasn't even born when "Return of the Jedi" came out... still there's clearly a little something between them, which is evident when Ryan puts his snuggly-slippered feet on the coffee table.
When he decides to start dating again, Ryan gets unexpected competition... from Olympian Shaun White!