Frayed at the edges writer Keith (Malik Yoba) is burning the candle at both ends, dating two women at once and always running to make a story deadline.
Problem is, he hasn't written anything good in months and his editor tells him so and unceremoniously fires him.
After a suggestion from friends to do a story about dating through the personal ads, he embarks on a mission: 30 dates in 30 nights.
He gives out his home number and uses his real name but goes on dates with women as an observer instead of a participant allowing them to share about their lives but never giving up any of his own background story.
When one women becomes really hard to shake, he puts up more defenses and starts to use a fake name and persona when he goes out.
He finishes the story but it's lacking any sort of personal element until he meets Leah (Stacy Dash), a women he's played phone tag with for the entire month.
She forces him to examine the way he lives his life and become more real with himself.