Karissa Daly has been through the wringer, experiencing bad date after bad date. She's had enough and she's ready to throw in the towel. That is until she runs into the one that got away, Alexander. Alex knew Karissa better than anyone. He still does. But there's only one problem. He's not available.

When Karissa sees Alex with a beautiful blonde, she knows she doesn't stand a chance. Especially after the way he smiled at her. That's a smile you don't see every day.

Still, Karissa wants Alex in her life. But can she settle for just friends? It'll take a lot of self-torture and a few more bad dates along the way to decide if she can finally let Alexander go. Will Karissa's past come back to haunt her, or will she find her true love enduring her Dates of Misfortune?