An accountant, who never quite grew out of his awkward teenage years, finds himself with a dating coach - she happens to be his high school crush as well. Thanks to his coach, he gets a pretty woman he has his sights on for some time, but realizes they are incompatible. Meanwhile, his dating lessons with his teenage crush reawaken old feelings. Not realizing the feelings are mutual, he finds himself unable to act on them due to his fear of being rejected by the one he truly loves.
Brooke D'Orsay
as Annie Hayes
Eric Mabius
as Harold White
Jody Thompson
as Claire Russell
Gina Holden
as Julie Owens
Panou
as Willie Taylor
Kathy Najimy
as Kim
Jesse Hutch
as Matt Schneider
Olivia Knowles
as Megan Russell
Barbara Tyson
as Harold's Mother
April Telek
as Meredith
