With her sharp sense of humor, Heather provides relationship counseling via her call-in radio program. One day when her program gets the top rating of the week, ousting Bud from the top slot, he approaches her with an unbelievable bet. He says that she should be able to get a man if she claims to be such an expert on relationships. Independent Heather doesn't particularly care about her appearance and she has no boyfriend, but she won't back down from Bud...so she accepts the bet! Can she win the man considered the sexiest bachelor and prosecutor in Chicago?