Let's see...
Our wedding: My father and the best man picked up their suits together and they fit great... too bad they were the wrong suits! Didn't realize that until we were walking out the door for the rehearsal and our best man asked why they were wearing "tails" to an afternoon wedding. WHAT?? Not really a disaster, but really funny watching my mother "deal" with the rental company.
My best friend's wedding: The bridal party did the bouquets the day before the wedding. They were simple, but pretty with pink roses and white orchids. The hotel kindly offered to put them in the cooler (West VA in July) until the next day and my husband offered to drive them to the church so they didn't have to sit in the unairconditioned building. Great- except they put them in the FREEZER instead of the refridgerator. My husband called me on my cell in a panic, stopped at three different grocery stores and bought every pink rose he could find. We "redid" them all one-by-one in the hallway and she didn't notice a thing until after the ceremony. She looked at me and said "I thought we had orchids in these!"
My husband's best friend's wedding: They all decided that it would be a "great idea" to go out for a few drinks after the rehearsal dinner. It was all fun and games until the groom fell off a bar stool and shattered his collar bone. My husband drove him to the ER and they didn't tell the bride until the reception.
My parents' wedding: The got married in Upstate NY the Saturday after a major snow storm, so there were issues all weekend. The funniest of which was the fact that everyone jumped in their cars after the ceremony to go to the reception and left my great grandmother sitting in a wheelchair on the front steps of the church. Everyone thought someone else had her! Ooops!
Oh well, all of the above marriages are happily intact and in the end that's what matters!