Chronologically Obi-Wan showed us, the audience, the "Blind Spot" trick that Solo performed in Empire during the Fett asteroid chase in Clones.
Was that a tip of the hat by Lucas to ESB (like Indy going for his gun in Temple of Doom) or did Obi-Wan and Solo talk about more than just the nature of the Force during their trip to Alderaan, a flight that would take 7 hours according to the Star Wars Fact Files.
Think about it - Solo was a hot pilot, as was (we have since learned) Kenobi. Seven hours is a long time, although through judicious editing it appears to be a trip that takes little more than a few minutes. But Tatooine in the Outer Rim to Alderaan in the interior would take a good long while (and that's 7 hours with no interuptions).
With both men wary of each other perhaps piloting was the one subject they had as a common ground.
Why not? Nowhere has there ever been a written description of what occured during the flight. Obviously it took a while, it was when Ben taught Luke everything he would know about the Force until Skywalker reached Dagobah.
So, what if they had one conversation on one subject that would later have great rammifications and enable Han, Leia and the gang to escape the clutches of Vader, for a short while at least...