Winston was so determined to talk to the old man in the pub of London's prole district because the prole is old enough to give a truthful account of the past.
Step-by-step explanation:
It is in this Chapter (8) Winston takes a huge risk and step to show his desperation in wanting to know the past. Winston is so desperate to know if someone else was feeling the way he was about the Big Brother and everything. It is this action that seals his destiny as his curiosity and need to know the history becomes transparent.
Indeed, Winston was so determined to talk to the old man in the pub of London's prole district because the prole is old enough to give a truthful account of the past. Yet, with no answers, he just ends up imagining the horrible party slogans and a place with no darkness.