Celebrating a half century of life warrants some good humored fun and jesting. A roast is typically when some carefully selected individuals close to the person being roasted make a speech or a toast poking fun at the individual with embarrassing stories and anecdotes. Be careful not to choose something too embarrassing or offensive, remember the roast is suppose to be in fun and everyone in attendance at the party will now be privy to the information and stories you share. Choose something humorous that even the person being roasted will laugh about.
Marriage and Dating
Choose a favorite anecdote about the person's dating life or early marriage years. Items for contention could range from a first date, marriage proposal, wedding or anniversary party. Choose something significantly back into the past to help minimize embarrassment for the birthday person. A wife or best friend would be ideal to regale the party with the details of this story. Use common sense in the specific stories that are brought up, for example, don't roast a man for his dating appetite if he is there with a new girlfriend. Choose humor and logic over any inappropriate or vulgar topics. Keep it appropriate to the age group as well as the guest list.
If the birthday person has been at the same job or with the same company for many years a boss or supervisor that he has a friendly relationship with or even a coworker will be ideal to poke fun at his work habits and methods. An old college buddy could have some humorous insights into his work habits and even a funny story or two about his first post-college interviews or an internship experience. This should also be kept fairly tame and tasteful, especially if there are professional associates present. Be careful not to divulge any classified information or stories that could get him into trouble, such as adventures in the company car or over-use of the company credit card. Keep it good-natured and playful.
A sibling is likely the best choice when it comes to dishing the dirt on the birthday individual. They will have knowledge of every scheme, every embarrassing story and every secret joke from birth to age 50. In lieu of a sibling, a childhood friend or even a parent or other family member would be able to provide some humorous insight and anecdotes as well. If possible, try contacting an early childhood teacher for some interesting memories about his early days at school. Refrain from revealing family secrets or embarrassing information about other family members apart from the one being roasted during these speeches.