Ryan and Simone are having a great time together, but when Ryan accidentally calls her Janie on a date, Simone worries he's holding back in their relationship and his deceased wife is the reason. Ryan promises Simone he's moved on, even if he's still wearing his wedding ring. She's not convinced, as memories of Janie are scattered all around his house. Simone gives Ryan an ultimatum - if he wants to prove he's over his wife, he's got to take off the ring.
In light of Simone's request, Ryan calls a secret meeting with the group at his office to help him figure out the best plan moving forward. Sonia immediately realizes Ryan's setting up a shadow group, and Steven quickly joins in. Everyone agrees Ryan shouldn't take off his ring unless he's doing it for his own reasons and has truly moved on from Janie. Anne shows up late because her nanny quit. In need of a babysitter on short notice, Mr. K enthusiastically volunteers - this is his chance to make something of himself.
Ryan opens up to Simone, telling her that while he simply isn't ready to take off his wedding ring, he still wants to continue their relationship. She's 31, and without a committed relationship Simone needs to move on with her life. In a desperate and grandiose romantic gesture, Ryan slings his ring off the side of the road. See? He can move on. But within seconds, Ryan is running into the brush and rolling down the hill after it, still unable to let go. Simone sees this as their relationship's final straw.
Mr. K shows up to his babysitting gig dressed in a Mary Poppins' style outfit. He's a little over the top, but Anne doesn't really have a choice, so he'll have to do. Anne gives strict instructions for her children to finish their homework, but when she leaves, Mr. K decides they should make a spaceship out of sofa cushions instead. Anne's set up a computer camera at her office to spy on Mr. K, so when she catches wind of his shenanigans she realizes she's made a mistake. Mr. K tells her she needs to learn to let go of her anxiety and ditches her web cam in a closet.
After Simone decides to move to San Francisco, Steven tries to lift Ryan's spirits by immediately throwing him back into the field. The two meet up with hot tub salesman Hughie, a friend - and irresistible party force - at a trendy downtown nightclub. Steven wants Hughie to help Ryan have some fun and get his mind off Simone. But when Steven runs off to hit on some ladies, Hughie breaks down and tells Ryan the single life is a slow, lonely death ride that's chipping away at his soul. He's a shell of man at this point, and all but demands Ryan patch things up with Simone before she's out of his life for good. The pep talk helps Ryan realize what he has to do.
Anne comes home fully prepared to lay into Mr. K for his negligent babysitting, but is instead greeted by her angelic children, dressed like the Von Trapp family, singing her a harmonious bedtime lullaby. The kids' homework is done, their teeth are brushed and house is spotlessly clean; somehow it looks better than when Anne left! Mr. K's such a great babysitter that the children beg to have him back. Anne's speechless.
Based on his behavior at group, Mr. K's new role as babysitter has gone to his head. He's treating the kids like his own now, just like a glorified, bragging parent, except of course they're not his kids. Anne's clearly uncomfortable with his enthusiasm. The group has mixed feelings about Ryan's chivalrous plan to drive up to San Francisco and ask Simone to move in with him, and Steven charges in hoping to kibosh it. Though most are caught up in the romanticism, Steven and Lauren know it's unhealthy. After all, there's a reason Ryan wouldn't take off his wedding ring before... Unfazed, Ryan calls Carrie and asks her to replace all his furniture with stuff Simone will like.
Anne's kids have become obsessed with Mr. K, so much so that they want him around all the time. Anne feels the pains of being emotionally replaced as she puts her daughter Abby to bed next to her Lite-Brite depiction of Mr. K - how come he can connect with the children so easily but she can't? When Abby's crisis peaks, Anne breaks down and calls K. He tells her she's trying to be the work of two kids. She needs to give herself the space to be a kid with her kids. The next time Mr. K comes over, he finds Anne inside a cardboard spaceship, laughing it up with her kids. Seeing the transformation, Mr. K tenders his resignation - his work here is done.
Ryan shows up at Simone's door in San Francisco ready to display his love for her. He's moved on from Janie and is ready to commit. But when Simone answers the door and her ex-fiance Marco's inside, Ryan pulls her onto the porch for a heart-to-heart. Simone's crazy about Ryan, and she's all in if his gesture truly is about her. But if it's just an attempt to replace Janie, he's got to let her go. This is their moment of truth... all Ryan has to do is say it's Simone and she'll jump in the car with him and drive back to Los Angeles.
Devastated, Ryan returns to Los Angeles without Simone only to find Carrie has replaced all his furniture per his request. Later, Steven and Lauren come over to cheer him up. Lauren sees his relationship with Simone as proof that he can move on from Janie, eventually. Steven is more optimistic, per "16 Candles" - he promises Ryan his Jake is looking for him and she's right around the corner. The three cuddle up on Ryan's new lady couch together and help Ryan realize that he'll never be alone as long as he has his friends.
Ryan's wedding ring gets in the way of romance; Mr. K babysits Anne's kids. Bradley Whitford guest stars.