It's Valentine's Day and Lydia is feeling jealous of Claude over a dozen roses she got from Charlie, who's on a road trip with his father. The next morning, two dozen roses mysteriously appear on Lydia's desk, and she wonders who is her secret admirer. Claude finds out it's Kipp, but decides to keep it down because no one would believe that. Meanwhile, Claude has the most embarrassing moment of her life when Will overhears her talking dirty with Kipp on the phone; and Owen is seduced by a gorgeous girl who only wants his sperm to make a baby, leaving Claude and Ramona the mission of opening his eyes not to let a child grow without a father.

After breaking up with Charlie, Claude is feeling low. Will's fiance insists Claude accompany her to a bridal salon, which only serves to upset Claude further. They run into Trista Rehn (star of ABC's reality show, The Bachelorette), who got engaged on the show and is trying on wedding gowns. Claude locks herself in a dressing room to cry, wiping her nose on a wedding gown, and Trista trys to comfort her through the door. Claude's friends rally round, even Lidia, and try to cheer Claude with an impromptu slumber party and girl talk.

In celebration of two years in NY, Claude decides to throw a party at her place. But when Will says he'll go (a direct result from his publicist's attempt to popularize his image), she changes her party from casual to fancy. The only thing she wasn't counting on was Will showing up in casual clothes and turning her party into exactly what she wanted to avoid. In the end Ramona questions Claude about the reasons of her sadness and shows her that even though her party might not be the fanciest people sure are having fun.