Danny Martin (Rob Lowe) and his pal, Bernie (James Belushi) are two young guys soaking up all that single life has to offer them in 1980’s Chicago. Until one night when Danny meets beautiful Debbie Sullivan (Demi Moore) at a bar. The two end up having what they and everyone else thinks will be just another one-night stand. But they decide to try to make a go of a full-fledged, let’s-move-in-together relationship out of it. This doesn’t sit well with Danny’s friend, Bernie, who feels he is losing his prowling buddy and best pal, nor with Debbie’s friend, Joan (Elizabeth Perkins) who thinks Debbie is making a big mistake. Add to that the everyday pressures involved in simply trying to maintain a relationship, especially when it involves two seemingly disparate people who maybe shouldn’t have gotten together in the first place, and the odds of them making it start to seem very long.