I TRIED to work mine so that everyone could be most comfortable, although nearly imposible because of the age differences with some of them.
Maid of Honor (college roommate- Andrea)-Best Man (Chris's brother that is 3 years younger than him)
Bridesmaid (college friend-Beth)- Groomsman (Chris's father)
Bridesmaid (another college friend - Karen)-Groomsman (Chris's youngest brother, who was 14 at the wedding)..definately the weirdest match
Bridesmaid (last college friend- Alison)-Groomsman (my best friend, Tim who I have known since we were 12)..I knew this would be the one my college friend would be most comfortable with
Jr Bridesmaid (Chris's cousin: Danay)- Jr Groomsman (my nephew: Michael)...the cutest match because his cousin is a year younger (but taller, lol) than my nephew.