Dash has nothing figured out. He's 33, broke, depressed and still in love with his ex, Lauren. Dash's world explodes when Lauren gets engaged to a man she barely knows. Life looks pretty hopeless for Dash until he meets Nora van Denbrock, a spontaneous, unforgettable woman. However, timing is everything, and Nora is not the type of woman who is going to wait around for Dash to figure out his life. Dash desperately needs to change. With his life crumbling around him, he does what every neurotic, immature, hopeless romantic, male would do. Dash goes for psychotherapy. Under the guidance of Dr. Goldberg, he navigates through the confusing labyrinth of love and faces the harsh realities of growing up. Unfortunately Dash is trapped in a perpetual state of unrequited love. He can't let go of the past. At the end of his rope, he is forced to make a huge decision that will change his life forever. And so the story goes: boy loses girl, boy meets new girl, boy loses mind, boy finds himself ...