Dr. Herman schedules lots of surgeries and steals a hospital couch. She teases Owen about taking the swiped sofa out for a spin. Amelia hears about this event during an awkward update. In other relationship news, Callie believes that everyone is getting freaky but her. Owen advises her to go meet someone. He suggests being honest. That’s what works for him. Callie sees why. So does Amelia, who pops by his place and leaves after getting a nice kiss.
Jo hops into the shower in front of Arizona. This leads to a series of awkward and embarrassing conversations throughout the day. Dr. Herman is actually impressed to hear about Arizona’s semi-sordid past. She had no idea she was such a dirty, dirty girl. Dr. Herman and Arizona trade stories about the people they used to be. They bond on that stolen sofa.
Richard has reconnected with Catherine, who promised to keep her distance from Jackson. That doesn’t happen. Catherine advises her son to stay out of his wife’s way, but don’t go too far. They both need something to occupy their time. Richard feels like that was his purpose for Catherine. This leads to a difficult conversation. Catherine leaves Richard to figure some things out. Only then will the two of them be able to move forward.
Ben and his brother, Curt, honor their father’s wishes by sprinkling his ashes in the woods. Bailey stands watch since what they are doing is illegal. Curt ends up collapsing in the woods. He’s rushed to the hospital. Curt has organ damage. Ben wants to find out what’s wrong with his brother ASAP. Bailey and Meredith already have an idea of what the issue is. A short time later, Curt starts coughing up blood.
While Curt is in surgery, Bailey breaks the news to Ben that his brother is transgender. This leads to a difficult conversation during the patient’s recovery. Curt has known he was this way since he was five. He’s tired of pretending. Ben is having trouble accepting this. He feels like their whole life together was a lie. Later, Jackson introduces himself to Curt, who wants to go by the name of Rosalind in the future. They go over the ground rules for the transition as Bailey compassionately watches from afar.
A woman, Hillary, is rushed into the OR. She took a spill down some steps after her boyfriend, Todd, was in mid-proposal. Hillary needs surgery. She admits that she faked fainting when Todd proposed because she didn’t know how to break his heart. So Callie does it for her. She dispenses a breakup by proxy. Todd is sent packing. Later, Callie ends up getting her game back on by picking up a hot guy at the bar.
Meredith is reluctant to dish on the details of her trip to meet up with Derek. Maggie knows it’s because she wasn’t with him. Meredith assures her that she’s not cheating on her husband. She basically tells her that the truth is none of her business. This has Maggie feeling like all the progress they’ve made with each other has been obliterated.
Meredith later admits that she just couldn’t get on the plane. She ended up hiding at a hotel by the airport. Maggie understands. Meredith also comes clean to Alex. She says that the three days she spent by herself turned out to be amazing. She doesn’t want to leave Derek, but she doesn’t want to be with him right now either. Alex gives her a hug as a pant-less Jo enters and promptly flees. He lets Mer know that he’s gonna marry that girl. As for Meredith, she doesn’t know what’s going to happen between her and Derek.