At least two people must play. At least three is better. More than six may get confusing. Determine the number of leaps. Six is good, or you can roll with 2d6. Reroll if you want. Each player makes up a character, with an age, a gender, a relationship, an occupation, or none. Some people are just lonely. You can use the dice to randomize that if you want. Then, all players decide how their characters are related or know each other. Then, leap as many times as decided above. For each leap, roll 1d100. That's the number of years you've gone back in time. You must decide if you're the same character. If your character is 37 and you've gone back two years, you probably are. If they're 16 and you've gone back 80 years, you must be someone else, probably an ancestor. But maybe someone was adopted. Maybe someone was forgotten. You must decide how your story led to your previous character. How do does everyone relate now? Do they even know each other? If so, will your previous characters ever find out? Will your stories remain parallel or were you a clan from many generations ago?
You shouldn’t be afraid to let this get funny or sad. Think ahead.