We meet Jules, a woman who at her twenties took on marriage and a baby instead of experiencing the dating scene. Now on her forties, she finds herself as a divorcee and eager to live the dating scene that she missed. With the help of her friend, Laurie, her younger co-worker who wants to show Jules to go out there and have fun. Ellie, her sarcastic, married and content to her average but lovable husband Andy. There's also her family, her ex-husband Bobby and her son Travis, who will test her patience, and her new forty-something divorced neighbour Gray, who doesn't believe that Jules can date again.

Jules tries to party hard like a twentysomething and ends up looking like a total fool, when even her best friend Ellie, told her not to do it. Travis discovers trying to avoid further embarrassment due to his father, Bobby, working at his school, can actually add to it. Jules gets as frustrated as she faces the physical limitations of her age.

Jules family and friends crash the 10th date with her new boyfriend, Josh. Ellie and Laurie help Jules realize that it's ok to be selfish once in a while, when Jules has a disastrous experience in bed with Josh. Meanwhile, Jules left Travis with Bobby, who has to be responsible and deal with his son.

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.

When Josh tells Jules he's in love with her, she knows the time has come to break things off with him. Unfortunately for Jules, she's not the best at ending relationships without hurting people's feelings, but thankfully she has the expertise of friends Laurie and Ellie to see her through. Meanwhile, Bobby, Grayson and Andy hit the links with money and pride on the line.

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.

Mad because her two best friends don't get along, Jules tries to have fun at her birthday. She finally convinces Ellie and Laurie to go with her on a wild birthday weekend, and they accept. But Jules encounters her nemesis with her flirtatious 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.

Scott Foley guest stars as Jeff, a very wealthy potential home buyer who is interested in one of Jules overpriced homes. Meanwhile, Ellie with reserves leaves the baby with Andy for a day to prove that she trusts in him.

Despite fearing the meanest and most unrelenting dermatologist in town, Dr. Amy Evans, Jules and Ellie are willing to endure the harsh ridicule and wrath for an appointment with the best in the business. But when Jules learns Dr. Evans is seeing Bobby, she's determined to stand up to her and protect him. Meanwhile, Travis gets a job working for Barb that turns out to be more than he bargained for.

When the relationship between Jules and her boyfriend start to heat up, Jules starts to get scared. Meanwhile, Laurie seeks diversion sex with an unsuspecting friend and Andy spills the beans about his big secret.

After her breakup with Jeff, Jules turns to Bobby for some cheering up. But when a bottle of wine leads to a passionate kiss, will they agree it was only a casual meaningless kiss? Meanwhile, Laurie discovers a thing that both Jules and Grayson have in common, while Travis plans with Kylie don't go as planned.

A hot tennis instructor gets between Ellie and Jules, while Laurie turns to Travis for advice, and Andy and Grayson try to cheer up Bobby after a fresh heartbreak over Jules.

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 mother 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.

Sara is a confident wine rep who sets her sights on Grayson; but is he strong enough to be her man? Meanwhile, when Ellie tells Jules she can't change past a certain age, Jules is determined to prove her wrong by giving up wine for a month; and Bobby's new dog poses some unwanted competition for Andy.

Jules and Sara hit it off, but when Grayson is overly attentive to his new girl, Jules warns him to back off before Sara pulls away. Meanwhile, Jules' perfect new bathroom complete with a "talking toilet" becomes the main attraction in her home and Grayson finds inspiration for a new song with a little help from Sara.

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.

Jules has mixed feelings when Travis gets accepted to two of his choice colleges. Now he must decide between schools in California or one just 20 minutes from home. As Jules struggles with the thought of Travis moving away, Grayson is there for her. Meanwhile, Laurie considers her feelings for Smith when he returns from law school, and Andy longs for the freedom to do whatever he wants around the house, free of Ellie's rules.

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

Despite Grayson's warning, a curious Jules reads the speech without permission and is left crushed when she finds she's not been acknowledged. Meanwhile, Ellie uncharacteristically does something nice for Laurie, and Bobby tries to restrain himself from embarrassing Travis on his big day.

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.