Plot hole: When Ike watches the video of Maggie's three weddings, he sees the rose tattoo on her back in her wedding to Gil. Then later, in Gil's garage, Ike is looking at a topless photo of Maggie from San Francisco when he notices that her tattoo isn't visible in the photo. Then he bets Gil that Maggie no longer has the tattoo. Gil is angry when he finds out Ike was right. But Maggie and Gil presumably broke up after their failed wedding, meaning that the San Francisco photo is from before the wedding. So why would Ike or Gil be surprised that Maggie has no tattoo in the photo? Ike should only suspect Maggie had her tattoo removed if the photo had been taken after the wedding. (00:38:00)
Continuity mistake: When Maggie and Ike are talking outside at the luau, Ike's flower necklace is in a different place every other shot. (01:11:15)
Continuity mistake: In one of the last scenes, on the balcony in NY where Maggie is telling him all the things she has realised, Ike asks if he needs to be writing these down. In the next shot, he is holding a piece of paper, yet she has never handed it to him.
Continuity mistake: When Ike and Maggie are on Ike's balcony in NY, at one point they are both sitting down facing each other. Ike gets up to turn the music on and he returns to Maggie. In the wide shot, his chair that he had been sitting in earlier has disappeared. It couldn't be hidden behind the door, because that would make him too far from Maggie when they were sitting face to face.
Continuity mistake: When Ike goes into the salon looking for Maggie, she notices who he is, and shows her friend the article. The article is lying on the counter. After they finish his hair, you can still see the newspaper article on the counter and in the last shot of him standing in front of the mirror, you can plainly see the article hanging on the mirror.
Continuity mistake: In the baseball game scene, Maggie's hair is several inches past her shoulders. In the very next scene that takes place the following morning at the beauty salon, her hair is only long enough to barely touch her shoulders. In the next scene, when Maggie breaks into Ike's hotel room, not only is her hair long again, but with the exception of the cowboy hat and an additional jacket, she's wearing the exact same outfit she wore the day before at the baseball game.
Continuity mistake: Timing of the proposal and wedding seems to be an issue. The church reader board announces Sunday morning to be the time for the cancelled and current wedding when we see a maintenance person picking off the name of the groom. Going backward, there is mention that the rehearsal is "two days before." You would assume since it's dark. it's probably Friday night. After that evening, you see a daytime montage of fun things going on with the couple. One of which is Richard Gere on the phone to New York, saying he's getting married in 36 hours. It's daylight. 36 hours prior to the Sunday am wedding would be Friday pm, just after the proposal, in the dark.
Factual error: Trying to cozy up to Ike, who she knows to be a Miles Davis fan, Maggie gives him a battered-up LP of Davis's "Kind of Blue" album, which he tells here is very rare. Truth is, "Kind of Blue" is one of the best-selling jazz albums of all time, and is not rare at all. Furthermore, the album and initial CD pressings had been (inadvertently) mastered at the wrong speed; the mistake wasn't corrected until relatively recent CD issues. The long-player is, in other words, virtually worthless on any count, especially in a jacket as beat-up as the one Maggie gives to Ike.
Plot hole: There are a few references in the movie about Cory, Peggy, Cousin Cindy, Maggie, etc. growing up together in Hale, Maryland (East coast). Why, then, does Peggy have an obvious Midwest accent? (I know 'Peggy' talks like this in real life; in the movie it seems out of place next to the other characters, who all sound the same).