Watch The Dating Coach
- 1 hr 24 min
When an insecure man hires his former high school crush to help shore up his disastrous dating efforts, they both unwittingly fall in love. Harold Gray is a successful, handsome man who still thinks he's the unpopular outcast he was back in high school. Needless to say, his complete lack of self-confidence has made him a disaster in the dating department. But Harold's life undergoes a radical change when he hires Annie Maxwell, his unrequited crush back in high school, to be his "dating coach."