Love is tough no matter whose looking. Caleb and Alejandra were about to be married but Caleb's ex-girlfriend has other plans and throws a monkey wrench in the happy couples wedding. Jewel is an attractive professional business woman and Ivonnah is her lesbian best friend. Both are two single women living in New York City who have all but given up on love. Each are equipped with an extensive repertoire of horrific anecdotes of dates gone awry. They both come together to help get Caleb and Alejandra get back together. When the reunited couple Alejandra and Caleb arrive at the conclusion that their friends need to find the one whose right for both of them, they undertake the task of helping Jewel and Ivonnah find love. But when Ivonnah develops a crush on Jewel things get complicated. Jewel has her sights set on her handsome single boss at work. With the help of Caleb and Alejandra, they attempt to get the objects of their affection out on blind dates. Only problem is neither Ivonnah nor Jewel have any knowledge of what the other is doing and on the night of their big dates, things go even more awry.