Geraldo Rivera as himself; Corey Parker as Lee Owens; Susie Duff as Kelly; Stephen Burleigh as William Aaron
Ellyn and Melissa join a video dating service just as Melissa contracts Lee Owens to re-paint her loft.
Ethan, cast as the Prince in a school production of Cinderella, has become a tad surly since discovering he has to kiss Susie Burrows, Cinderella. Ellyn gets a cat named Sophie from the pound that hates everybody, including Ellyn. While trying to meet the cat, Melissa and Ellyn start to debate blind dates and if a dating service is a truly ridiculous possibility. Melissa tells Michael about the deal and he laughs and swears not to tell. While filling out the application, Lee Owens comes to paint Melissa's apartment and fix the damage that Melissa has done.
Melissa and Ellyn have an extremely awkward (and amusing) time recording their messages at the dating service as Melissa's interviewer was in her ninth grade math class and Ellyn gets a cowlick. Melissa finds a guy in the dating book that she likes very much and thinks is practically perfect. Meanwhile, Ethan is resisting learning his lines or how to dance. Melissa, who has always loved Cinderella, takes pity on him, talks some, and teaches him to waltz. A bunch of losers have requested to see Melissa and Ellyn, and the man that Melissa wanted sent his video to Ellyn. Lee continues painting the apartment while blasting music, reading Melissa's books and rifling through the lingerie drawers.
Melissa finally works up the guts to ask William to view her video. Gary comes to the apartment to pick up some proofs that Melissa did and they're tentative, but civil. She asks if a shoe (a man's loafer) that she found in the closet belongs to him, but it doesn't. Lee arrives in the middle of this and comes across as extremely young, but nice. Melissa goes out with William and he turns out to be a total drag, completely unlike his video, and into The Monkees no less.
Meanwhile, Ellyn is waiting for "Dave" in the restaurant, having nightmare fantasies starring Geraldo Rivera doing a show "The New Old Maids" in which Hope and Michael castigate her from a backlit screen, then comes out of it and bolts before "Dave" can show up. Talking to Hope, Ellyn begins to confront what she perceives as everyone else's expectations that she needs to be with someone in order to be happy. In a silly moment, they jump into a photo booth and take funny pictures.
Lee and Melissa have established a funny little domestic routine, which is disrupted when he gets two tickets for them to see Lyle Lovett and Melissa is put off balance and even gets a little angry. She goes to Ethan's play and everything goes well, including the kiss, which sparks off a revelation about her situation. Ellyn settles in comfortably to her singleness and seems very at peace with it.
Lee is just packing up at the loft, so he and Melissa try to settle last details, including if the loafer belongs to him. It doesn't, but it fits and he keeps it. As Melissa tries to pay him, Lee persists, they kiss and end up in bed as the clock strikes 12.
Clip of Melissa and Ellyn looking under the bed; clip of Lee kissing Melissa; clip of Melissa looking down her dress; clip of Ellyn shifting around in her chair Hope throws away a baby gift (blanket?) that Emily Burch gave them Melissa once had a thing for Mark Lindsay of Paul Revere and the Raiders Lee definitely isn't into religion and hates Melissa's coffee Hope throws away a half-eaten ice cream cone In one of the photos, Ellyn points at Hope's nose There were no title credits in the opening segment for some reason
Note: much of the music from this episode has been dubbed over with generic stuff as the music licenses have run out, which is a crying shame (note to quote Roy Orbison).
"All I Want" (written by Joni Mitchell, from her album Blue) is sung by Polly Draper as Ellyn records her video dating ad
"Broken Arrow" (written and performed by Robbie Robertson from his self-titled album) plays as Lee and Melissa first kiss
"I must be on some mailing list marked 'Pitiful'." --Ellyn
"I don't like to impose my vision on other people until I'm sure they have no vision of their own." --Lee
"Love means never having to go on another date." --Ellyn
"Oh God, I hope it's not humid tomorrow. If it does, my hair will frizz and I'll look like Bob Dylan in drag." --Melissa