Perhaps they are brothers and their close friends. The brothers often hang out with this group and this particular night out is filled with family - like bonding, lots of laughter and shared secrets.
It could be about a group of friends going to a sports event. They cheer for their favorite team, share some beers and have a great time bonding over their love for the sport.
A boys night out trainwreck could be like this. They planned to go play pool at a local pub. One of the guys thought he was really good at pool but in reality, he was not. He kept making bets with other people at the pub. When he lost every single bet, he didn't have enough money to pay up. His friends had to chip in to cover his losses. And then he got really angry and started yelling at the other players, which made the whole atmosphere in the pub very tense.
Well, once on a boys night out, we decided to go bar - hopping. We started at this one place where one of the guys had a bit too much to drink way too quickly. He then tried to show off his 'dancing skills' which were more like flailing around. He accidentally knocked over a waitress who was carrying a tray of drinks. It was a total mess. Everyone was staring at us and we had to quickly apologize and help clean up. Needless to say, it was an embarrassing start to the night.
A series of unfortunate events can lead to a terrible night out. For instance, you plan to see a movie but the theater has a power outage right when the movie is about to start. Then you try to find another activity, but everywhere you go is full or closed. You end up spending the whole night just wandering around feeling frustrated and disappointed.
One night, I went to a concert. It started to rain heavily on my way there. By the time I arrived, I was soaked. Inside the venue, the sound system was malfunctioning, making a horrible screeching noise. Then I lost my wallet, and I couldn't even buy a drink to warm myself up. It was a truly terrible night out.