Tom (Braff) and Sofia (Peet) have just had their first baby and that means it is time for Tom to grow up. But, when Tom goes to work for his father-in-law, his new boss Chip (Bateman) seems to have it out for him. Tom soon discovers that Chip is still carrying a flame for Sophia from their high school days. Now, Chip will stop at nothing to see Tom out of the company and out of Sophia's life. As the two go head to head, Tom must expose Chip's dirty tricks and push him out of the picture forever.