After her recent divorce, Jules decides to put herself “out there” again, much to the embarrassment of her teenage son.
After lamenting she did not have any “war stories” from partying in her 20's, Laurie takes Jules out to make up for lost time.
Jules and Josh arrive at their 10th date, but the night is a disaster. Meanwhile, Travis is embarrassed when his dad starts living in a boat in a parking lot.
Bobby and Travis try to find common ground. Jules is upset that Grayson doesn't think she's attractive, and Ellie is upset that being a mother has changed what guys think of her.
Jules organizes a golf outing to help Bobby. Laurie woos a new client at the office.
Jules freaks out when Josh tells her he's in love with her, and Bobby tries to find a way to make some fast money to pay some debts.
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.
Ellie and Laurie threaten to ruin Jules' birthday vacation because they refuse to get along. Back at home, Travis plays a trick on Grayson after he breaks up a visit from a female companion.
It's Thanksgiving Day, and Bobby and Grayson awkwardly discover that they share the same ideal mate–Jules, while Jules is busy accidentally sabotaging Travis' plans with his Thanksgiving date.
Jules gets a date with a sexy topless jeans model, but she also develops unlikely feelings for an obnoxious client. Meanwhile, Bobby tries to bond with Grayson, and Ellie lets Andy take care of their baby for the day.
Jules becomes jealous when she learns that her cruel dermatologist is seeing Bobby, Andy gives Travis a lesson about understanding women, and Laurie lets politics get in the way of a potential hookup.
Jules freaks out when she decides to be exclusive with Jeff, which makes Bobby and Grayson jealous, Meanwhile, Laurie seeks revenge sex with an unsuspecting stranger, and Travis and Grayson try to save her.
In the aftermath of her breakup with Jeff, Jules turns to Bobby for some solace. When a bottle of wine leads to a passionate kiss, will they both agree it was casual and meaningless? Meanwhile, Laurie discovers a common thread between Jules and Grayson, and Travis' plans for a night with girlfriend Kylie don't go exactly as planned.
A hot tennis instructor gets between Ellie and Jules, Laurie turns to Travis to be her conscience, and Andy and Grayson try to comfort Bobby who is nursing a fresh heartbreak over his ex-wife.
Jules and Bobby debate on whether to let Travis go to a party where alcohol will be served. Laurie meets Smith's father.
Laurie's free-spending mom shows up just as she prepares to buy a house and needs a co-signer, Bobby is teased after he is robbed by a woman, while Travis helps take care of Barbara after a procedure from her dermatologist.
Ellie starts a fight with Andy after he buys a motorcycle, but it doesn't end the way she planned. Meanwhile, Grayson and Jules argue over whether men and women can just be friends, and Bobby takes Travis on an unusual fishing trip.
A wine rep is interested in Grayson. Andy's friendship with Bobby is curtailed by Bobby's new dog, and Jules tries to convince Ellie she can stop drinking wine for a month.
Sarah helps Grayson write a new song, but Jules advises him not to act so needy around her. Jules' new bathroom gets rave reviews.
Jules helps Travis when his relationship with Kylie hits a rough patch, while Sara is starting to wonder about Grayson's relationship to Jules. Andy is worried about his son not looking like him.
Laurie seeks to reunite with Smith when he returns from law school. Jules is conflicted when Travis gets accepted to two different colleges: one close by and one far away.
Jules and Grayson try to be “friends with benefits.” Bobby's newest money-making scheme inadvertently helps Travis. Andy hires a nanny.
At Travis' graduation, Bobby tries not to make a scene, but Jules makes one when Travis doesn't mention her in his speech.
Jules and Grayson must figure out a way to tell Bobby they're a couple. Travis misses an important anniversary with Kylie.