Jack Kelly has recently been thinking about the girl who got away. He has written a play about all his past relationships that didn't seem to work out. As he begins to direct the play with his actors he keeps thinking about Carolyn and why they were not together. We he let it go or decide to try and find Carolyn again and reconnect. He asks many of his friends and co workers what he should do when he finally decides to follow his heart or maybe not...