The episode begins with Gray introducing Jane to Christen. Gray tells Jane that after she is free, they need to talk; she leaves. Christen tells her that he has been distracting Gray for the past ten minutes. He then shows Jane the newspapers; Beau is getting engaged to a top designer. Jane is shocked. Jane reaches office and breaks this news to Eli and India. India tells them that this will be devastating to Gray and Jane will have to break this news to her. Gray calls Jane and talks to her about Jeremy; it is all over the town. That is why she hasn’t looked into the internet or the papers, as she is finding the whole Jeremy thing very embarrassing. Jane suggests that she shouldn’t see the papers for a while.
But then Jane breaks the news to her and Gray breaks a vase. At home, Jane discusses Gray’s situation with her mother, Kate. Kate tells her that Gray needs to get back to the dating scene. She suggests online dating. At school, Zoe tells Billy that she wants him to meet her parents. Billy is a little unsure. Zoe signs up for the school play. Jane finds Billy in a serious mood and asks him the reason. Billy tells her about his Saturday meeting. Jane is upset and feels that Billy has moved on. Amanda wants Nick to audition for her play. Rita arrives at school; she is dressed to kill, but she ends up being pushed around by the students. She is embarrassed. Amanda finds this funny. Jane goes to check on Rita. Rita feels that Ben is over her and breaking up with him was a mistake. She feels that she cannot compete with Amanda. Jane tells Rita to be herself.
Lulu and her friend suggest to Rita that she needs to step it up a bit as being herself means being single for the rest of her life! At home, Kate tells Jane that she has created an online dating profile for Gray. Jane is uncertain about this idea. Next, Amanda is on stage, welcoming the students for the auditions. Amanda likes Zoe’s audition. Jane tries talking to Gray about dating; but she reminds Jane that she is her assistant and they cannot do girl talk. Just then one of Gray’s friends Tamara walks up to her. She offers Gray a job but Gray declines the offer. Next is the audition for Cinderella’s Prince Charming; and it involves a kiss. She would like to demonstrate the kiss and so she chooses Ben! She kisses Ben on stage and Rita leaves the auditorium. At office, Jane is checking the online profile Kate made for Gray. Eli sees it.
Eli thinks it isn’t a good idea. India joins them and thinks it is a great idea. Just then Gray calls Jane and shows her the article which mentions her meeting with Tamara Mellon and as she feared the press made it look as if she is leaving Donovon Decker and joining Tamara Mellon. Donovon calls Gray. Gray convinces him with a bit of effort. India takes advantage of this situation and calls Tamara’s office posing as Gray’s assistant and fixes a dinner appointment with Tamara. Meanwhile, Jane tries to delete Gray’s online profile, when she sees that Gray has an admirer. She shows it to Eli. The man wants to meet Gray at the same place where India has booked an appointment for Gray with Tamara; same time, same place! At school, Amanda puts up the cast list.
Lulu and her friend Harper play the evil step sisters while Zoe gets to play Cinderella. And Nick is the Prince charming! Billy doesn’t seem too happy; first Lulu and now Zoe? At office, Jane tells Gray about the dating profile and surprisingly, Gray seems interested. Lulu and Harper once again tell Rita about stepping it up. This time she agrees. At home, Kate arranges Ben’s closet and Jane tells her that fitting in 8 years on parenting in a week is too much. Billy arrives and tells Jane that he wants her help. He wants her to make him a little more presentable. He tells Jane that she is the first girl who wants him to meet her parents and that means a lot. Jane tells him to be himself. Just then Jane gets a call from Tamara’s office telling her that Tamara would be 20 minutes late for the meeting with Gray; 5.20 at the Boathouse instead of 5. Jane realizes this is India’s doing. She is so dead.
Eli tells Gray that he is sorry about the engagement. Gray is upset about the fact that Beau has known the girl for just few months and he is already getting married to her. Gray tells him about her date. Jane tries calling Gray; but she isn’t picking up. Jane thinks that India would be waiting with photographers to click pictures of Gray with Tamara so that she could put them online for Donovon to see; she is so right! Billy offers to ride Jane to the city; but the car breaks down. Jane texts Eli and asks him to stop Gray from going on the date. He is on it. Jane asks Kate to come get them. But Kate is about to leave, one of her ex-boyfriends shows up on her door; Dakoda. Amanda and Ben go to a bar. They meet Rita there. And as usual Amanda begins to flirt with Ben. Rita decides to teach Amanda a lesson by emptying a bottle of tobacco in Amanda’s drink.
They realize that it was Rita’s doing. Amanda pretends that she is choking and when Ben goes to get some water, she tells Rita never to mess with her. Ben is disappointed that Rita did something like this. Kate arrives with Dakoda to pick up Jane and Billy; she is late and as a result there is just half an hour left for Billy to meet Zoe’s parents and Jane to stop Gray’s meeting with Tamara. Billy says that it is more important to stop Gray. Jane reluctantly agrees. Kate and Dakoda are arguing about their breakup; Dakoda has brought the goodbye letter with him as well. They finally arrive at their destination, Zoe’s castle! Billy is nervous. He rings the bell and Zoe opens the door. Zoe introduces Billy to her dads; she has two dads. Jane thanks Kate for her help. Kate is sorry about Gray and realizes that at times she tries a little too hard. She just wants to be a part of her daughter’s life.
Jane assures her that she is a part of her life. She then goes to check on what happened with Gray. She sees a message from Eli telling her that he couldn’t stop Gray as he was too late. Just then Gray appears on Jane’s screen. Jane apologizes to her. But Gray tells her that she didn’t go to the boathouse as he couldn’t go through with the date; she is not ready yet. But she thanks Jane for her efforts. Jane is relieved. She comes out of her room to tell her mom. And she is shocked. She sees Dakoda kneeling on one knee, holding up a ring to Kate and asking her to marry him! the episode ends at this point.