Spread

Spread is a 2009 romantic comedy film that follows the life of a charming and handsome gigolo named Nikki, played by Ashton Kutcher, who lives in Los Angeles and makes a living by seducing wealthy women. He meets his match when he encounters Heather, played by Margarita Levieva, a beautiful waitress who is not easily charmed by his advances. The two engage in a series of flirtatious and sexually charged interactions, but their relationships are complicated by their conflicting desires for love and money. The film features an ensemble cast, including Anne Heche as Samantha, Sebastian Stan as Harry, Ashley Johnson as Eva, Rachel Blanchard as Emily, Sonia Rockwell as Christina, Eric Balfour as Sean, Hart Bochner as Will, Reeve Carney as Band Leader. Directed by David Mackenzie.

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Some movies that have similar genres and were produced around the same time as Spread include She's Out of My League, Her, Silver Linings Playbook, I Now Pronounce You Chuck & Larry, 50 First Dates, Yes Man.