Thomas Nichols thinks he has life beat. He’s successful, handsome, has loving friends and family and a longtime girlfriend who adores him. How can he go wrong? By being unfaithful! One night it all comes to a halt when Lori catches him with another woman. He wants her back but the only problem is she doesn’t want him. Some brainstorming with his buddies leads him to the elaborate though twisted scheme that he has to convince her of his changed ways by getting engaged. But when all the women he asks keep saying no it throws him into a serious predicament. Don’t all women want to marry? What’s going on! Beaten, he then sets out to romance the only woman left he can find showing any remote interest in him but when she says no he’s left with no other choices but to seek his friends help once again. What results is more hilarious and entertaining advice leading to a series of attempts and failures at gaining her hand in marriage. But just when he’s about to pop the question again. Lori wants him back. He then has to decide between her and Jamie which leads him to realize what he’s been searching for all along has been right in front of him. But before he can reunite with Jamie he’s got to win the approval of inter-office employee’s. Prove he’s changed and mended his womanizing ways, confess his scheme and convince her she’s the only one for him. Will Jamie say yes? Or, will it be just another engagement.