A group of guys have made a deal to each invest in a fund, which would be paid to the last remaining bachelor of the group. Michael Delaney, a cartoonist, attempts to get the other remaining bachelor, Kyle Brenner, married to a statuesque policewoman who Kyle said was the one that got away, so Michael can claim the fund to pay off a gambling debt. Unfortunately, the policewoman Kyle is trying to marry is the woman Michael has fallen in love with, Officer Natalie Parker.