What conclusions does Winston come to while he is at the bar?

Answer: He wants to know from the older man whether life before the revolution was better or worse.

Explanation:

In his interview with Elder Winston, he hopes to find out what life was like in the past, more specifically, before the revolution. This is the main reason Winston engaged in dialogue. Winston escorted the older man to the pub and treated him to a few beers, thus starting the conversation and trying to find out.