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In Freeze the Day, Grayson proposes to Vanessa, who says yes. At the end of the episode, Grayson is hit by a car, and Vanessa and Grayson's relationship seems uncertain after Grayson sees Jane and calls her Deb on the verge of unconciousness.
The season starts with Hit and Run, in which Grayson is in a coma after the accident. Jane is hopeful that he knows who she really is, but when he wakes up, he can't remember anything about the accident or afterwards. In fact, Vanessa and Grayson move their wedding day up.
In False Alarm, Grayson asks Jane to help plan their wedding, and she agrees. She gives him a wedding planning scrapbook she (as Deb) had made for her and Grayson's wedding, but replaces the picture with one of Vanessa and Grayson.
In Dream Big, Vanessa asks Grayson to ask her father for her hand in marriage, because her father had been disappointed when he didn't before. Grayson agrees, but continues to put it off. But then Vanessa's father turns out to be the judge presiding over Grayson's current case, so he eventually asks for Vanessa's hand in marriage.
In The Wedding, Vanessa wants Grayson to learn how to waltz before the wedding, so he asks Jane to teach him. Vanessa sees them during the lesson, and is upset at how close they look. At Vanessa and Grayson's wedding, Vanessa is late. Jane goes to check on her and Vanessa tells her she can't marry Grayson, because something is missing in their relationship, and she (and Grayson) deserves better. Jane tells her to let Grayson know face-to-face, but she refuses, saying that she's not that brave. She then leaves in a limo.
Grayson struggles to move on from Vanessa, but eventually manages, and begins seeing a woman named Cassie.
Vanessa appears in Season 5 in Fool for Love. She is Kim's opposing lawyer. She is also married and pregnant. Kim first sees her in a ladies' restroom, and they awkwardly make small talk. Vanessa gets a call from her husband, who had gotten them a "Bug-a-Boo" stroller, the best stroller there was. Vanessa is thrilled, and boasts to Kim. Kim says that she wasn't getting baby things from designer or "label" brands to teach her child modesty, and Vanessa quips that Kim would have to get rid of her designer clothes and accessories.
After Vanessa leaves, Kim calls Paul and tells him to get her a "Bug-a-Boo" stroller. During court, Kim has Grayson bring in a cart full of documents and drawings to illistrate her client's contributions toward her late boyfriend's game, Forever More. The sight of Grayson throws Vanessa off, and Vanessa thinks Kim had Grayson specifically bring in the cart to mess with her. Vanessa also tells Kim that the stroller Paul had gotten for her was a "Bug-a-Boo" knockoff.
Vanessa and Grayson talk and manage to resolve their issues with each other, and Vanessa wishes Grayson happiness. Kim wins her case, and afterwards, when Vanessa makes a disparaging remark, Paul pretends to be Kim's boyfriend to stop her. This is likely Vanessa's last appearance.
Grayson was dating Deb and was planning to propose before her accident occurred. Grayson spends a lot of time trying to get over Deb but it isn't til season 2 when he plans on proposing to his girlfriend at the time, Vanessa.
- Vanessa has blunt bangs in her Season 5 appearance.