Goofs

As Willie, Tommy, and Gina are exiting the drugstore (after her rant about guys unrealistic physical expectations of women) the signage of the store clearly reflects Valentine's Day season, while several times the movie shows it's Christmas season.

When Andera first meets the guys in Stinky's bar she orders six shots of whiskey. She pours four of the six glasses and pauses to hand the fourth glass to Willie. It cuts back to three empty glasses. Two fill up and then it cuts away to her face as she pours the seventh shot but she keeps pouring, at least three shot glasses worth.

Willie and Tracy's car becomes clean as they drive away at the end.

Paul's windshield wipers while plowing Jan's driveway the first time.

Paul's tie when deciding whether or not to go to the reunion.

When Willie is playing in the bar, when Andera sits down next to the piano, the keys are not moving in sync with the melody being played. At first, the keys hardly appear to move at all, as Timothy Hutton is not depressing them but just moving his fingers over them.

Peter the Eater does not look old enough to have been in high school with Darian.

One plot hole says Peter the Eater, actor Tom Gibis, does not look old enough to have been in high school with Darian, actor Lauren Holly. Gibis is only 10 months younger than Holly and older than many of the other actors cast as classmates.

Gina mentions to Sarah that she looks like Ally Sheedy from The Breakfast Club (1985) with the Estevez Brothers. Ally Sheedy and Emilio Estevez were in Breakfast Club but his brother Charlie Sheen (Carlos Irwin Estevez) was not.

In the piano scene at Johnson Inn while flirting with Willie, Andera (trying to show her coolness and "guy knowledge") says "Pitchers and catchers report in two months, three weeks and six days." Since the movie takes place a few days after Christmas, this time frame would have Spring Training beginning around last week of March/beginning of April... when Pitchers and Catchers would really report around early February.