Jules, a recently divorced single mother, begins to explore the ins and outs of dating in a culture obsessed with youth and beauty.

Despite Ellie’s advice, Jules decides to try to keep up with the partying twentysomethings. However, things do not go as Jules had planned.

Jules’ family and friends impede on her all-important tenth date with new boyfriend Josh, When putting the needs of others before her own results in a disastrous experience in bed with her new boyfriend, friends Ellie and Laurie help Jules to realize it’s ok to be a little selfish and take care of yourself once in awhile. Meanwhile Bobby is left to behave like a responsible dad and deal with son Travis.

When Jules inadvertently tells Grayson he’s hot and he doesn’t reciprocate, she’s on a mission to get him to admit she’s sexy. With a little help from Laurie and Ellie, Jules uncovers the ultimate burn to put Grayson in his place. Meanwhile, Ellie is feeling like she’s lost her looks after the birth of Stan, and Bobby and Travis search for something to bond over.

Jules rues the day when her ex-husband, Bobby, and Grayson become fast friends over a mercy golf lesson that she organized to help boost Bobby’s self esteem. Meanwhile, Laurie surprises even herself when she takes on a new client to prove her worth to Jules.

Once Josh tells Jules he loves her, she decides to break things off. Elsewhere, Grayson, Bobby and Andy make a bet during a golf match.

Jules always seems to be with her friends, her ex or her son. One night when everyone is busy, she reluctantly takes a date with an older man just to get out of the house, so Grayson makes her a wager that she can’t spend a whole day by herself.

Upset that her two best friends aren’t getting along, yet determined to have a great birthday, Jules has Ellie and Laurie go with her on a weekend away. However, Jules has an encounter with her husband.

Jules plan for a romanctic dinner for two backfires for Thanksgiving. Travis shows off his girlfriend Kylie to everyone. Jules gives Travis and Kylie advice on birth control. Bobby and Grayson bond over a common interest...

A wealthy man (Scott Foley) has an ulterior motive in his search for an expensive home; Ellie tests her trust of Andy by leaving their baby with him for a day.

Despite their fear of the meanest dermatologist in town, Dr. Amy Evans, Jules and Ellia are willing to endure the wrath for an appointment with the best in the business. However, after Jules learns that Dr. Evans is seeing Bobby, she's determined to protect him from her. Meanwhile, Travis' new job, which is working for Barb, turns out being more than what he bargained for. '

Jules panics when things begin to heat up between her and her new boyfriend. Meanwhile, Laurie tries to sleep with a friend; and Andy reveals his big secret. '

Jules turns to Bobby for comfort after breaking up with Jeff, but when they kiss after too much to drink they insist the kiss was meaningless. Meanwhile, Laurie finds a link between Jules and Grayson, and Travis' plans with his girlfriend don't go as he had hoped. '

A hot tennis instructor pits Ellie and Jules against one another. Meanwhile, Laurie cant' get Travis out of her mind, and Andy and Grayson try to comfort Bobby who is heartbroken. '

Jules, not wanting to spend Valentine's Day alone, turns to Grayson to keep her company when everyone else makes plans. Meanwhile, Bobby and Jules take different sides when Travis asks to go to a party where they know he will be drinking; Ellie tries to prove she is the alpha dog, not Grayson; and Laurie meets Smith's father. '

Laurie needs a co-signer to buy her first condo and finds her less than stellar, absentee no help at all. Meanwhile, Bobby is mugged by a woman and Travis comes to Barb's aid after her latest cosmetic surgery procedure.

Jules is determined to prove to Grayson that women and men can be friends without any sexual undertones. Meanwhile, with Jules' encouragement, Andy buys a motorcycle from Laurie -- to Ellie's dismay -- and Travis joins Bobby on a man-trip for some "noodling," only to be mortified by his discovery of what noodling actually is.

A wine rep sets her sights on Grayson; Jules vows to give up wine for a month.

Jules thinks Grayson is overly attentive to his new girlfriend, Sara; Jules' new bathroom becomes the main attraction in her house.

Jules is thrilled for the chance to take care of Travis after his first big break-up. But when Jules discovers the truth about the break-up, she comes to an unwelcome realization about herself. Meanwhile, Sara considers whether Jules threatens her relationship with Grayson and turns to Ellie for guidance; and Andy searches for any resemblance between himself and son Stan.

When Travis is accepted into some of his choice colleges, Jules has mixed feelings; Smith returns from law school.

Jules and Grayson consider the notion of FWB, friends with benefits. Meanwhile Andy hires a nanny for Ellie, and Travis benefits from Bobby's unconventional plans to make some extra cash

Jules encourages Travis to submit a graduation speech; Ellie does something uncharacteristically nice for Laurie; Bobby tries to refrain from embarrassing Travis.

Jules and Grayson hatch an elaborate plan to break the news to Bobby that they're officially dating, and Travis sees the wrath of a truly angry woman for the first time when he forgets his momentous seven-month anniversary with Kylie