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Straight from the Heart (2003). A Hallmark movie.

Jordan Donovan (Teri Polo), a photographer from New York City, is set up with Tyler Ross (Andrew McCarthy), a Wyoming rancher, by her roommate after her boyfriend fails to commit. Jordan flies to Wyoming to meet Tyler and his sister Laurie and her fiancé. Jordan learns his sister placed his ad in the singles magazine for him. Although Tyler is initially put off by Jordan's city slicker attitude, they find themselves drawn to each other.