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 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.