Harry becomes an overnight father figure to nine-year-old Billy and teenage Anastasia, who both seem to be the product of Harry's past foray into sperm donation. Meanwhile Harry meets Rose, a beautiful, if neurotic, single woman who's out to have a baby on her own, and who believes Harry may have what she needs to get pregnant.
Harry helps Billy’s moms, Zoey and Michelle, to encourage Billy to be cooler at school. Meanwhile Jonathan and Janet fear their daughter Anastasia may be failing French, and administer an I.Q. test to Harry, fearing she got the ‘dumb gene’ from him. Harry and Rose square off about the future of Rose’s potential child.
Harry signs Billy up for Rhythmic Gymnastics, so that Harry can hook up with the hot new gymnastics teacher. Meanwhile Jonathan offers Harry $5000 to disappear from his daughter’s life. Rose strikes up a friendship with Irene, who Harry fears will tell Rose all of Harry’s dirty secrets.
Double-booked, Harry must decide between scoring with a hot fashion model or attending his baby's first ultrasound.
Harry helps Billy become his school’s top charity salesman, while Rose tests her maternal instincts on an electronic baby.
Rose hides her pregnancy from her boss, while Harry discovers the truth about Jonathan and Janet's sex life.
Harry figures out the secret behind Rose’s new boyfriend, while Zoey and Michelle deal with consequences of Billy having lice.
When Janet diagnoses Harry with Sympathetic Pregnancy, Rose finds that she’s competing for sympathy with her new, narcissistic belly-buddy, Harry. Meanwhile Zoey and Michelle rejoice after finding a babysitter (Leah Feidh Fassett) Harry can’t hit on – because she’s a lesbian. Janet discovers Jonathan has been seeing another therapist behind her back, Dr. Meinertzhagen (guest star Tom Green).
Harry helps Rose to make friends in her new birthing class, while Janet and Jonathan fight for the chance to be involved in Anastasia's prom.
Harry coaxes out Rose's bachelor side when they are forced to share an apartment. Zoey's grandmother plays a visit, and Rachel goes behind Jonathan's back in an attempt to get a good deal on a car.
Harry lies about having a relationship with Rose to score with a home-wrecker; Jonathan and Janet attempt to connect with Anastasia online.
Rose lies to make a preschool waitlist; while Zoey and Michelle attempt to give Billy 'The Talk'
Roses's pregnancy nears full term, prompting Zoey and Michelle to contemplate whether they will ever want another child of their own.
Harry, Michelle and Zoey dole out conflicting love advice to Billy, while Harry tries to deal with his newly discovered crush on Rose. Meanwhile, Rose can't wait to start dating a cute father at her baby's play group, but she’s not happy when she finds Harry spying on her date. Jonathan is thrilled to come to Harry's rescue, since Janet and Anastasia aren't interested in his advice.
Harry's feelings for Rose mean he's not interested in dating other women, but Zoey, Michelle and Janet convince him to date the director of Billy's school play. Meanwhile, Jonathan tells Rose about Harry's feelings for her, but Rose doesn't believe it when she catches Harry in a compromising situation.
With the sperm bank out of Harry’s 'stuff,' Zoey and Michelle go straight to the source. But Harry refuses to put out, forcing Zoey and Michelle to confront the reality of another baby. Meanwhile, Rose wants her boyfriend Bruce to get along with Harry, and Janet and Jonathan try to rekindle their 'happy marriage' – with disastrous results.
Rose tricks Harry into babysitting so she can have her first sex date with new boyfriend Bruce, but is furious when Harry leaves baby Charlie with Janet, whose 'baby whispering' skills are put to the test. Meanwhile, Zoey worries that Billy is slow for not figuring out her homemade holiday, 'Gaia Day,' isn't real.
Harry becomes jealous of Billy and Jonathon's new bond, while Rose tries to spice things up with Bruce.
Rose tries to put Harry's 'single dad powers' to good use, while Michelle, Zoey, Janet and Jonathon confront their bedroom fantasies.
Harry and Rose tell Rose´s judgemental mom a lie in order to keep her happy; and Michelle and Zoey turn to Jonathan for help preparing their wills.
Harry conquers a dating obstacle that brings Rose´s insecurities to the fore; at the same time, Michelle and Billy find themselves drawn into Zoey's war on sugar.
Harry hopes to raise the families’ opinion of him by introducing them to his delinquent big brother Frank, but Harry realizes he may be the family black sheep after Frank charms everyone.
Charlie isn't meeting his milestones fast enough.
Rose quickly gets over her initial annoyance with Harry dating baby Charlie's pediatrician after she comes to realize the perks of having a doctor on call.
Harry tries not to panic when he and his new girlfriend reach a landmark date. At the same time, Janet and Jonathan try to deny just how freaked out they are about teaching Anastasia how to drive.
Feelings are mixed over the possibility that Harry isn't actually the sperm-donor dad of Anastasia and Billy. Elsewhere, Rose admits to herself that she has feelings for baby Charlie's father.
