As a sometimes ill-equipped but always devoted single parent to his two adolescent daughters, Grace and Natalie, Wade is taking the major step of dating again. His supportive and compassionate best friends, Forrest and his wife, Delia, and Ben and his wife, Michelle, are thrilled he's resurfaced and enthusiastically offer to help set up his online profile.
Wade suddenly finds himself in a "relationship" he has no interest in when he has trouble turning down a second date. Also, Wade tries to understand when Grace struggles with her social media posts.
When Wade's friends encourage him to join a support group for partners who have lost a spouse to help him deal with his anger, Wade's shocked by the advice he's given by the host of the support group, Caroline.
When Wade changes the password to his online dating profile because his friends become too involved, Forrest goes to great lengths to keep tabs on him; Grace and Natalie are torn when a show they watched with their mom returns for a new season.
When Grace gets the lead in the school musical, Wade realizes that the teachers are giving her special treatment after he hears her sing; Michelle and Ben persuade Delia and Forrest to volunteer for snack bar duty at a school function.
When Wade visits a local hot spot to meet people instead of using his dating app, Forrest and Ben decide to be his wing men.
When Wade goes out of town for the day, he panics at the realization that he is the sole caretaker of his children; Delia picks up the girls from school for Wade, but is thrown for a loop when Grace tells a clever lie to hang out with her friends.
Wade and the girls tackle hosting a traditional Thanksgiving dinner for friends and extended family; Ben attempts to make a fried turkey for the first time.
Wade pretends to be dating Caroline to avoid being set up on blind dates by Delia. Also, Ben and Michelle throw an anniversary party for themselves, but have issues with the catering.
Wade is giddy, his daughters are amused and his friends are excited when he has his first crush since becoming single again. Also, Grace and Natalie take advantage of their dad going on dates by having friends over and it starts to get out of hand.
Wade considers moving his relationship forward with Anna if his daughters approve of her after they all meet. Also, Delia, Grace and Natalie realize how priceless their memories are of Jill are as they prepare to sell some of her belongings at a garage sale.
The women from the Widow's Support Group offer Wade unexpected advice for getting out of his dating rut. Also, while Michelle is recovering from gallbladder surgery, Delia relentlessly pushes her to follow strict medical advice.
When Wade decides to redo his will, he is conflicted about who should get custody of his children. Also, Michelle tries to convince Ben to get a vasectomy after they have a pregnancy scare.
Wade convinces Forrest to take his career advice, and the results are disastrous. Also, Ben lands a lucrative opportunity for his company, but Michelle is uncomfortable embracing their success.
When Wade has a bad date with Natalie's friend's mother, Natalie ends up paying the price. Also, Forrest finds unusual ways to fill his time during his unemployment, and Ben has a conflict with his daughter Sahai's basketball coach.
When Wade lands a job for Denny, a newly divorced, wealthy client, he realizes Denny is only interested in using Wade to meet women. Also, Meg applies her expertise as an accountant to get Wade's finances on track, and Forrest and Delia attempt to clear the tension between them by having an argument.
Wade analyzes his feelings about his casual relationship with Caroline. Also, Delia and Michelle help Grace work through an awkward middle-school phase.
As Grace prepares to attend her first dance, Wade strongly feels Jill's absence and leans on his friends to get through it. Also, Wade, Forrest, Delia, Ben and Michelle reflect on growing older and the changes their lives have undergone in the past year.