Addison locks herself in the bathroom after Jake doesn't give her an answer about getting married. He didn't say yes, but he didn't say no either. Jake just wants to make sure they are ready for such a big step. He often has chats with the vision of his dead wife, Lily, to help deal with life's little curveballs. It's helpful self-therapy especially when he has an upcoming meeting with social worker Mildred, who needs to evaluate his role in Henry's life. That's nothing compared to the shock he feels upon meeting his daughter's much, much older boyfriend.
Angela's new boyfriend happens to be her college professor, Eli. They met in class. The guy teaches human sexuality. Yikes! Jake is thrilled that his daughter has found a man 30 years her senior who makes her happy. Wait a minute! No, he's not. He's furious! He's also upset to learn that he needs to be fingerprinted as part of a background check for Henry. There's an incident in Jake's past where he beat up his wife's drug dealer. Things go from bad to worse for Jake when he tells Angela how he truly feels about her new boyfriend.
Jake's patient, Megan, is hoping the fifth time will be the charm with her latest attempt to have a baby. With her husband out of town all the time, she's constantly calling Jake for the littlest of things. Addison doesn't think this is healthy for either doctor or patient. This leads to a big blowup between her and Jake. They call a cease fire in order to host a dinner with Angela and Eli. It doesn't go well. Jake lets the college prof know that his relationship with his daughter ends now. He makes a not-so-subtle threat to the guy.