Ryan is thrilled to bring home a larger-than-life-sized cutout of himself. The only place he can find to put it is currently occupied by Janie's sewing machine, so he decides to give the sewing machine to Sonia, since hers broke. Everyone's happy except Lauren. It's a really big deal to start giving Janie's possessions away. The shirt she sewed for Ryan may have been terrible, but she sewed it with love. Ryan doesn't need to suppress his feelings; they have tissues and a safe space. Ryan reacts with sarcasm, prompting disbelief from the others. When Lauren goes for the cry, she usually gets it. Lauren denies that she goes for the cry; however, she does think crying is cathartic. Mr. K breaks into tears, asking, "Why, why?"
At work, Ryan's excited to learn a spot has opened up on Jeremy Roenick's hockey team - did Carrie call to get him in yet? Steven realizes Carrie already called and was denied because Roenick hates Ryan. You'd think there'd be no downside to constantly insulting people on the air... When Steven realizes Carrie didn't use the dead wife card, he picks up the phone and guilts Roenick into letting Ryan onto his team.
Overjoyed, Ryan announces his upcoming hockey game to the group, then frowns to see they're making therapeutic collages about their pasts and futures. Anne speaks up. She's been invited to a wedding, the first since her partner died, and she doesn't think she can face it alone. Anne is surprised to learn Ryan understands, and even more surprised when he offers to be her date. Lauren clasps Anne's hands - this is a great idea! Anne wants to think about it, but Ryan warns her not to take too long, or Lauren will go for the cry. Anne accepts his offer, cry denied.
Steven cheers on the sidelines during Ryan's first hockey game. Roenick tells the other guys to go easy on Ryan since his wife just died, and consequently, Ryan's head inflates - he's killing this game! When Ryan gets on his knees, searching for a lost contact, Steven lets Roenick believe he's crying. On the way to the wedding, Anne asks Ryan if he's wearing glasses to look smarter. He claims he's wearing them to see, and he promises to show her a great time; he's her wingman for the night.
Ryan quickly realizes that this wedding is a lesbian wedding. He's impressed when random women approach him to thank him for the good work he's doing on his show. Clearly it's a smart crowd. Ryan notices a woman checking Anne out and encourages her to say hello, but Anne insists she's not ready yet. Ryan decides to check out Sasha anyway and returns to tell Anne that she's a cool single mom, too. It's not long before Sasha makes her move, and ready or not, Anne is in the midst of flirtation. Ryan hits the bar, and when another woman approaches him with kudos for his journalistic integrity, he realizes she thinks he's Rachel Maddow.
Back at the office, Ryan is just telling Steven he's going to start a fight on the ice, when Carrie bumps into Ryan in the hall. Why does she hit harder than Jeremy Roenick? Carrie reports that Lauren called to see if he's feeling okay about the sewing machine, so Ryan tells her to call his group and invite them to his next game, to prove he's doing just fine. While Ryan heads into the studio to do his show, Sonia shares her latest collages with Lauren, who wants to send the links to Ryan - for inspiration. When Ryan sees a collage of Sonia making a cat bathing suit with Janie's sewing machine, he starts crying on the air. Once again, Lauren has gotten her cry.
Ryan walks into group, asking if anyone has heard any good radio shows lately. Everyone's now calling him "Cryin' King," so its kudos to Lauren, since she got her cry. Lauren insists it wasn't her intention to make Ryan cry at work. It turns out Ryan is now crying over just about anything. He was fine, but Lauren broke him; and now she has to fix him. Lauren explains that he isn't broken; Ryan needs to slow down and feel his feelings - maybe making a collage will help.
Anne storms into the group - she has a stalker! Sasha wants to meet her for a drink, and Anne doesn't know what to do. Claiming other people's problems are easy, Ryan suggests Anne meet Sasha for a fruit smoothie at a time when she's clearly on her way to do something else. Later at home, Ryan tries making his collage, thanking God when there's a knock on the door. Anne charges in - Sasha tried to kiss her, and she freaked out! She's not ready and she doesn't think she'll ever be ready. Ryan feels the same way - they both want to move forward - so Anne grabs him and kisses him. That's the first kiss out of the way. A milestone! Progress!
Steven sits down for a talk with Ryan just as his next hockey game is about to begin. Crying on the air didn't go over too well with his target audience. When Ryan claims he's turning over a new leaf of radical honesty to avoid further outbursts, Steven admits to playing the dead wife card. The other hockey players are letting him win. On the ice, Ryan tells the guys to stop taking it easy on him. He's ready for honesty, and they can bring it on! Unfortunately for Ryan, the truth hurts, as the guys start hitting him with a vengeance. At the end of the game, Roenick gleefully takes a photo of Ryan, beaten to a pulp.
Ryan uses Roenick's photo as the centerpiece of his collage, which makes Lauren get teary-eyed. Everyone admits it feels good to cry. At another hockey game, Roenick admits Ryan's starting to hold his own. When a group of figure skaters take the ice, Ryan's heckles are met with recognition. Rachel Maddow plays hockey, too?
Ryan's stoked to get an invite to join Jeremy Roenick's hockey game - but there's a catch!