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.

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.”

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.

After Wade has an instant connection with a woman he met briefly in a parking lot, he’s determined to find her again. Also, Michelle waits to hear from the colleges she applied to for her business degree, and Natalie tries to convince Wade she’s old enough to get her ears pierced.

Wade and the girls tackle hosting Thanksgiving dinner for friends and extended family. Also, Ben attempts to make a fried turkey for the very first time.

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.

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.

He learns quickly that he has to come to terms with her unusual living arrangements if he wants to keep seeing her. Also, Grace is struggling with fitting in at her new high school, Michelle grapples with her algebra college course and Delia tries to help Forrest fit in with his much younger colleagues.

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.

Wade, Forrest and Ben decide to schedule colonoscopy appointments at the same time after they learn that Ben is scared to go. Also, Michelle tries to avoid her sister Meg's boyfriend drama, but Delia winds up getting over-involved in Meg's issues.

After Forrest gifts a water gun to Noah, Ben and Michele quickly take it away, and the group has a frank discussion about racial injustice. Also, Wade is trying to figure out how to celebrate Shannon's birthday since their relationship is so new.

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.

When Grace gets the lead in the school musical, Wade realizes that the teachers are giving her special treatment after he hears her sing. Also, Michelle and Ben persuade Delia and Forrest to volunteer for the chaotic snack bar duty at a school function.

After Ben recommends Wade for a job on the same work site he's on, they are surprised by their wildly different professional styles. Also, Delia is struggling to not be so judgmental about how Michelle is raising her kids.

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 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.

Natalie realizes that her memories of her mom are starting to fade when Michelle and Delia have a memorial to honor Wade’s wife. Also, Forrest and Ben get competitive when their kids enter a fundraising contest at school.

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.