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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. Written by
Why is the teenage dork always named "Harold" (who grows up to be an accountant)? Talk about Hollywood stereotypes!
"Ugly Betty's" Eric Mabius, playing a grown-up Harold White, finds that Annie Hayes, his homecoming dance date when they were freshmen in high school, has returned to town, and is unable to find employment in her chosen profession as party planner. Annie is played by Brooke D'Orsay, of "Royal Pains" and "Drop Dead Diva" fame.
At the prodding of a buddy, Harold tries to hire a dating coach, but it doesn't work out. Instead, he hires Annie to become his coach (it helps to supplement her waitress income), and she does such a good job that at one point, the student winds up teaching the teacher.
The ending of this movie is preordained from the outset, but it gives the viewer a nice ride along the way. It also works as a decent how-to dating guide for nerds everywhere.
A slimmed-down Kathy Najimy plays Brooke's co-worker; and prospective first date, Gina Holden, never looked better.
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