Cal and his wife Emily are high school sweethearts who have been married for 25 years when Emily suddenly asks Cal for a divorce. After moving out, Cal spends his evenings at the bar whining about the situation when he meets a young, handsome man named Jacob. After learning of the situation, Jacob helps Cal adjust back to the singles scene by training him on how to be attractive to women. After awhile, Cal is successful and is able to pick up some women. However, he still finds himself in love with Emily. Meanwhile, Jacob meets a young woman named Hannah to whom he is very attracted and much more interested than his usual one night stands.