Five questions - one long story. Borderline non-geeky but parts of it qualify. Identify and connect :-)

Cracked by gudanggurum , Goyal , akhi , shenoyvarun86 (close enough ), Achilles , Ajay Parasuram , uday , sidsen and Bipin Banavalikar.

Gurupad, Goyal, akhi, shenoyvarun86, Achilles, Ajay Parasuram, uday, sidsen and Bipin Banavalikar