This movie came out in 2007 and stars Diane Keaton and Mandy Moore. Although it did not do well with the critics, I enjoyed it for what it was, a light hearted, funny, romantic chick flick.
Is is about a mother (Diane Keaton) who has been divorced for much of her life and she is worried that her youngest daughter (Mandy Moore) will end up like her. The mother places a personal ad to try and find "Mr. Right" for her daughter. She thinks she finds the perfect man but her plans get messed up when a jazz singer inserts himself into the quest. The daughter falls for both of them, ultimately having to make a decision as to who is the right man for her.
In the end, both mother and daughter find love. Here is a clip from the movie showing the daughter dating both men and ultimately who she chooses. The clip is set to "Black horse and the cherry tree" by KT Tunstall, which is in the movie.