The episode begins with Jake asking Addison who has shut herself in the bathroom to open the door. Addison is embarrassed because she proposed to Jake and he froze. “I didn’t say no” Jake says. “You didn’t say anything” Addison counters. In the end he manages to convince Addison to open the door. Jake tells Addison he wants them to get married but “not right now”. He basically isn’t ready for it yet, he tells her. Addison on hearing this locks herself in the bathroom once again. The problem is Jake still hasn’t gotten over his dead wife. Flash forward to two weeks later, and Jake is still contemplating about Addison’s proposal.
Addison asks Jake to not think about it and to let it go. Addison says her social worker Mildred wants to meet Jake in order to find out more about him. Basically Mildred has to keep checking on things till Henry is officially Addison’s. At work, Violet is having a talk with Sarah’s parents. Sarah is the little girl who went missing from St. Ambrose a few weeks ago. Violet discovers Sarah’s mother Dana is becoming dependent on prescription pills she had given and therefore decides to wean her off them. James is doing is best to become friends with Amelia, but she is doing her best to resist his attempts. Jake and Addison run into Angela, Jake’s daughter, outside a movie theatre. Jake and Addison are surprised to see that Angela is dating a middle aged man named Eli Wilson. Turns out, Eli teaches human sexuality and Angela met Eli “in class”.
Jake is apparently not happy, with Angela’s choice of boyfriend. Next day, Addison discusses Angela and her boyfriend with the rest of the gang. Violet confesses that she during her college days had slept with as many as 3 professors. Sam feels Angela’s relationship is completely inappropriate. “There is something wrong with this professor guy, he needs to find a playmate his own age” Sam concludes. Addison says Jake will have lunch with Angela and try to talk reason with her. They all know that won’t work out well. Jake in the meantime, is in a meeting with Mildred. Mildred takes Jake’s fingerprint in order to run a background check. Jake seems a bit reluctant but relents.
Later he tells Addison that he had been jail for a night and later had to do community service, for beating the crap out of a drug dealer, who was bothering his wife and child. Addison is worried on hearing this, as she doesn’t want any impediments in Henry’s adoption procedure. Jake assures her that, nothing will go wrong. Later at lunch, Jakes tells Angela, she dating Eli isn’t really a great idea. Angela makes it clear to him that she doesn’t need his permission. “I’m trying to protect you” Jake says. “I don’t need protection” Angela counters. She tells Jake that she loves him but she also loves Eli. She begs Jake to not make her choose between the two of them. James asks Amelia out on a date and as usual she begins resisting, but seems to be considering it. Jake tells Addison how his meeting with Angela went.
She asks him to not push Angela too hard, or she shall end up marrying Eli. Addison feels Angela is a smart girl and will therefore make the right decision in the end. “You need to suck it up and invite them over for dinner” Addison suggests. Jake then attends to his patient Megan, who has had a number of miscarriages in the past. She is worried she might have a miscarriage again and asks Jake to stay with her for a little while, as her husband is out of town. Later at home, Addison and Jake discuss about Megan and her issue. “I think that the level of doctoring that Megan needs is bordering on unreasonable” Addison says.
Jake doesn’t agree with Addison’s conclusion, but Addison feels Megan is simply making excuses to see Jake. “You are so kind and so available that you make it easy for patients to take advantage of you” Addison says. Addison feels Jake has to set boundaries. “Stop trying to tell me how to practice medicine” Jake tells Addison in agitation. Addison says that his choices also affect her life. “How is it that you can commit to these women, but you can’t commit to me?” she asks in anger. Jake makes it clear that it’s his job to take good care of his patients and he is not going to stop that just because she wants him to.
Next day at work, Jake has a talk with Amelia and tells her James is a good guy and that she should give him a chance. “You deserve to be happy. Be happy Amelia” Jake says. In the night at home, Jake and Addison have dinner with Eli and Angela. Jake is unable to control his emotions during dinner and walks away from the dinner table as a result. Eli follows Jake in order to have a talk with him. Eli explains to Jake that Angela is very special to him. Jake feels, all Eli is doing is looking for an ego boost, but Eli disputes that. “When you finished your PhD, she was in diapers” Jake says. Eli tells Jake that he isn’t a bad guy and sincerely tells Jake that he loves her. Jake though, is in no mood to relent.
Eli makes it clear that he won’t stop seeing Angela. “I’m not asking you I am telling you, this has to end” Jake warns Eli. “Or what?” Eli asks. “You don’t want to find out” Jake replies. Violet asks Sarah’s parents to not move on, but at least live their lives. She tells them that, at some point probably “it will start hurting a little less”. Megan calls Jake to her house in the middle of the night saying she is experiencing pain and cramping. Jake pays her a visit and calms her down. He says she is fine and assures her he will be by her side through the pregnancy. Megan then tries to kiss him. He pushes her away visibly shocked. He makes it clear to her that he is just her doctor.
But, Megan feels her and Jake have a “special connection” and says she can feel it. “Megan I am sorry if you misunderstood” Jake says and walks away. Next day, Jake calls Megan to his office and hands her a list of doctors. “I think its best you choose someone else to see you through your pregnancy” Jake says. She reminds him that he had promised he would be by her side. “That was before my level of care was being misinterpreted” Jake replies.
Megan runs into Addison outside Jake’s office and lies to her that Jake made a pass at her and tried to kiss her. Jake hears this and comes out to protest. Addison on her part sees through Megan’s lie and reprimands her for accusing a man, who has always tried to help her. Megan then quietly walks away. Amelia meets up with James for a date. Jake says a yes to Addison’s proposal, in the most romantic way possible. He then gives her a ring. The episode ends.