Molly (Jolie Jenkins) jumps in when Romy can't join Sarah to audition for a jingle-singing gig, which they win. But a tragedy precludes them from doing the job. Douglas: Vincent Angell. Hatcher: Mark Tymchyshyn. Romy: Jennifer Garner. Maguire: Jonathon Schaech.
“Difficult” defines Sarah's new charge as an au pair; a smitten dentist hires Cecelia as his receptionist; Maguire and J.B. enter the party-DJ business; Sarah disdains 21st-birthday fanfare. Sophie: Mia Kork. Flynn: Erika Christensen. Ashley: Elizabeth Mitchell. Leya: Andrea Abenoza. Spencer: Patrick Fabian.
A contest to see who can have the first meaningful dating experience leads Joss, Romy and Sarah to men with varieties of baggage. Cyril: Mailon Rivera. Oliver: Larry Poindexter. Ethan: Gabriel Mann. Walt: Jay Harrington. Randall: Shawn Christian. Connor: Taylor Sheridan. Alleya: Arreale Davis. Arnetta: Shirley Prestia.
As the millennium approaches, Maguire is robbed, Joss is fired and Sarah learns of their “arrangement”---after Romy kicks her out; J.B. stumbles into a dream date for the event. Angela: Robin LaMorte. Jessica: Samantha Smith. Archer: Denis Arndt. Peter: Don Perry. Adele: Pamela Gordon.
Sarah gets a break working for a personal shopper; Joss's problematic sister visits; Cecelia gets a health warning; J.B. crosses a line with Romy, who meets Joan. Casey: Tammy Townsend. Audrey: Heidi Mokrycki. Joss's Mother: Jenifer Lewis. Joan: Faye Grant. Charge Nurse: Octavia L. Spencer. Joss's Father: Wendle Wright.
Sarah learns a dark part of Maguire's past after the arrival of his former crony (Jeremy Renner); Romy presses the issue of J.B.'s lack of intimacy toward her. Joan: Faye Grant. Dean: Christian Mills. Claire: Elizabeth Bogush. Evan: Thomas Burr. Romy: Jennifer Garner. Maguire: Johnathon Schaech. J.B.: Diego Serrano. Sarah: Jennifer Love Hewitt.
After a snag in her recording plans, Sarah finds herself hosting Thanksgiving for a quirky quartet of Maguire; aspiring suitors Spencer and Tony; and a former opera conductor (John Billingsley). Tony: Rino Romano. Spencer: Patrick Fabian. Maguire: Johnathon Schaech. Romy: Jennifer Garner. Sarah: Jennifer Love Hewitt.
Sarah is steered toward a singing career by a well-connected man interested in more than music; J.B. is unavailable to celebrate Romy's role on a soap. Tony: Rino Romano. Joan: Faye Grant. Mitchell: Robert Cicchini. Director: Bruce Nozick. Dee Dee: Kim Oja. Mollie: Romy Rosemont.
Romy and Sarah throw a singles party for profit; word from Bailey leads Sarah to do “something outrageous”; Maguire gets jealous when a musician pal (Robb Derringer) hits on Joss. Spencer: Patrick Fabian. Andy: Eric Matheny. Fred: Matthew Frauman. Maguire: Johnathon Schaech. Romy: Jennifer Garner. Joss: Gina Ravera. Sarah: Jennifer Love Hewitt.
Sarah is hired as personal assistant to a matron with a menagerie; Maguire expresses feelings for Sarah; Romy and J.B. have their first date. Spencer: Patrick Fabian. Mrs. Halloway: Janet Carroll. Archer: Denis Arndt. Romy: Jennifer Garner. J.B.: Diego Serrano. Maguire: Johnathon Schaech. Joss: Gina Ravera. Sarah: Jennifer Love Hewitt.
Twenty-year-old Sarah Merrin (Jennifer Love Hewitt) goes to New York City to find her biological father. Archer: Denis Arndt. Billy: RuPaul Charles. Maguire: Johnathon Schaech. Romy: Jennifer Garner. Joss: Gina Ravera. Cecelia: Pauley Perrette. J.B.: Diego Serrano.