In this romantic comedy Jack and Jade, who have been best friends since childhood are both dating all the wrong people. After a date they meet up and discuss how horrible it was. Their dates generally go from bad to worse. Jack has been on dates where the girl is marrying them on the first date and Jade has been on dates where the guy asks her to help him rob a bank. They continue on down this long road to love leaning on each other through all the wrong turns.