Jane by Design starts with Gray (Andie MacDowell) jetting off to make nice with Donovan (Decker) after the debacle with Jeremy and the sighting with Tamara Mellon. She gives last minute instructions to Jane (Erica Dasher) about a dress for Nina Garcia. Eli (Bryan Dechart) asks Jane out to dinner at a fancy restaurant, by implying that she was a wallflower and that she doesn't know how to dress. Smooth talker, that Eli.
The next morning, Jane tries on the dress she's been working on for weeks, just waiting for the perfect time to wear it. She tells Billy (Nick Roux), who's over of course, that Eli has finally asked her out, and it's not all awkward (yes, it is). And then she asks him to unzip her. These two have the weirdest non-relationship.
Ben (David Clayton Rogers) has been sleeping on the couch because Kate (Teri Hatcher) and Dakota (John Brotherton) have taken over his room while Dakota waits for an answer to his proposal. As Jane, Billy and Ben are talking in the living room, Kate comes out of Ben's bedroom on Dakota's back. She asks Ben if he minds if they take a shower first. You can almost see the images flashing across the kids faces and their abject horror.
Billy is helping out on stage design for the school play. He's just a bit jealous about Nick (Matthew Atkinson) playing the prince since he isn't really over the double betrayal of Lulu and Nick. Jane tries to convince him that he has nothing to worry about. Which is when Amanda (Briga Heelan) waltzes over to rhapsodize over the chemistry between Nick and Zoe (Mariah Buzolin). Amanda had a busy morning. Earlier, she stopped by Rita's (Smith Cho) office to show her the poster sized yearbook photos she had made up for Ben. She had Rita's done so Ben could see the near miss he had there. Lovely lady, that Amanda. Rita tells Amanda she wins.
Amanda sets up candles all over Ben's office, but when Ben gets into his office, he's not in any mood to talk or even be seduced. The scout from "The Surprise" (refresh your memory here) is back with a minor league try out offer for Ben. Between not being over Rita and that, he's nowhere near to being ready to even think about Amanda. Especially not when she keeps calling Rita "Shaw the Jaw." Amanda is floored.
Kate has been working on the costumes for the play. She thought it would be a way for her to spend time with Jane, but of course Jane has been busy. As Jane looks for her dress so she can leave, Zoe appears in the dress. She thought it was for Cinderella, and she obviously feels beautiful in it (it's a one shouldered affair, silver and sort of grecian-styled on top and white on the bottom). Jane cannot bring herself to crush her mom since she seems so excited that Jane worked on a costume.
At the office, Jane asks Carter (Ser'Darius Blain) if he thinks the dress she has on is okay for dinner. He doesn't. Nina Garcia's assistant arrives for her dress. Jane is surprised to see that there are two of the "one of a kind" dresses. It turns out tha Donovan always makes a back up just in case, but she's never needed it, and the assistant leaves the dress with Jane. Can you see where this is going? Jane puts on the soft white dress. It's sleeveless and has a peplum. The top is kind of interesting, but doesn't look like anything the Project Runway star usually wears.
At dinner, Jane and Eli talk about her amazing dress and how weirdly adult they feel. When guess who walks in wearing guess what? Jane ducks under the table. When Eli joins her there, she explains the situation. He gives her his jacket and she runs to the bathroom. Unfortunately, while doing that she bumps into a waiter holding a full glass of red wine and he dumps the entire thing on Nina.
While Jane is in the bathroom, she gets a call from Nina asking for the back up dress. She grabs a tablecloth from a passing waiter. She changes and somehow drapes a plunging neckline dress out of the tablecloth for herself, just in time to hand the back up dress to Nina. Nina thanks her and tells her she'll let Gray know how helpful she was, and (!) she tells her she likes what she's wearing. Eli and Jane head out and have street cart hot dogs. He tells her this is the best first date he's ever had. They kiss. Really? The age difference isn't a little weird and icky? Not that he knows of course, but still!
Billy catches Zoe and Nick talking about falling in love and breaking it to him and tells Zoe that she was a "colossal waste of time." Of course it turns out that they are running lines from a rewrite. Zoe is understandably upset. Nick tells Billy that he'll drop out of the play. That's going to really annoy Amanda if she still has a job. Turns out that there's a budget problem and the one hold out on the budget committee is Rita. Amanda tells Rita that since she and Ben wouldn't be long term, she thinks Rita should go for it.
When Jane gets home from her date, Dakota has given Kate an ultimatum. Jane convinces her to go with Dakota, and she does, promising that she won't just disappear. Ben comes home excited because he got an offer from the AA team, and now that Kate is here...Jane doesn't tell him.
Rita meets Ben at the bus. She doesn't tell him she changed her mind when he says he feels like this is all kismet. Ben leaves and Jane dances around her house realizing she is all alone. Jane by Design meets Risky Business?