"What do you say, Jay? Will you be my Wingman?"

Newly divorced, Jay McGraw finds himself standing at the edge of a life he never planned. Quietly bruised by love, he feels he's not ready for a new romance.

Enter Shawn Jay's longtime best friend, musician, and unapologetic chaos engine. Where Jay is thoughtful and stable, Shawn is impulsive and unsteady especially when it comes to women.

Together these two have navigated bars, dance floors, and relationships for years, with Jay reliably playing the role of Wingman setting up conversations, smoothing over awkward moments, and stepping aside when things turn serious.

Yet, when a night out to celebrate Jay's divorce and to help him meet a new potential love leads to an unexpected connection, his old patterns begin to crack.

Shortly after Jay is introduced to Jill a sharp, grounded teacher with her own complicated dating life he's asked to be her Wingman. He's done this for woman in the past, of course. But somehow this particular ask seems different. And it's not until later that Jay is forced to confront an uncomfortable truth about himself: he's always been great at guiding people toward love, but terrible at claiming it for himself.

Jay slowly realizes that, sometimes, the hardest person to be a Wingman for ... is yourself.