Ellie becomes frustrated with Andy's omni-presence now that he doesn't have a job or a hobby to get him out of the house. She realizes that Bobby's boat is empty now, and she plans to use it as her own personal escape.
Laurie and Travis realize that Tom might be the awkward weird neighbor to them, but he is the Dr. McDreamy of his hospital at work. Laurie encourages him to ask out one of the young hot doctors that he works with, but Tom doesn't want to date a colleague.
Ellie arrives at Bobby's boat, but she finds Grayson has already claimed the boat as his secret retreat. They decided to duke it out over the boat to decide who gets to keep it.
Jules encourages Andy to get a new job, and he promises to make some calls. When he realizes that interviews are more rigorous than he remembers, Jules and Travis coach him through some practice interviews to get him ready.
Tom asks out not one but four of the sexy doctors from work. Laurie finds out and gets upset that she's given him the confidence to two-time innocent girls. Eventually, all the girls show up at Grayson's bar and have it out over Tom.
Back at the boat, Ellie and Grayson's rivalry gets destructive when they accidentally slash a tire that keeps the boat upright. The whole thing flips over on its side.
During the practice interviews, Jules realizes that Andy might not be ready to get back into the working world. He tells Ellie that he wants to be a stay at home Dad, which means she'd have to go back to work. Ellie is more than ready to make that compromise, since her battle with Grayson made her realize that she's bored with her life.
Laurie tells Tom that he has to chose between the skeevy Tom that no one likes and the nice Tom that has good friends. She enlists Jules to play along and tell him how much she misses seeing him since he's become "cool."