Getting together with a group of people from school often provides a mixed bag of emotions for many. Some of them are excited because their life has been successful, and they want to share their glory. Other people see it as a time when they are forced to take a good look at the failings of their life. They dread seeing the successful people, and might only go to see one or two cherished friends. It is a time for reflection and rediscovering lost goals of the individual or group.
There are people who are desperate to appear successful to their former classmates. They might have done nothing in the intervening years worth note, so they work to make up for that. Bringing a good looking date with them is often seen as a way to indicate success. After all, a beautiful person would never fall for a failure is their reasoning.