I feel bad for Vulpes the first time I played New Vegas and got to Nipton, if I knew he was so cool I wouldn't have harmed him
Oh and Caesar on my first play through I never noticed the Medicine check before doing the surgery
Cass on a hardcoe playthrough by 3/5 Cazadores, she had no chance with that caravan shotgun of hers
And my D.i.D charcter Marc Antony, he completed everything but was taken down by a irradiated heavy trooper at the Long 15