Did Sam piss Al off?

Well, obviously that stung and Al left shortly thereafter. Was he angry? Maybe a little, but arguably he felt more insulted and embarrassed that through Sam's Swiss cheese brain, that's an opinion he can still have about Al. Sam wasn't proud of what he said to Al or to Seymour, and he did his best to be contrite; while Al admitted he was wrong to underestimate Sam's perspective and opinion about Allison.


"Our families are in there! Our, uh, mothers and... and tiny, tiny babies!"

I'm sure Sam pissed off Al lots of times, including in the scene you're mentioning. Sam really hit below the belt sometimes. He could also be a spoiled brat. In fact that's why the scene in 'The Leap Home' where Al tells Sam it's damn fair is so great. And Al's not mean about it or anything. He just tells Sam what's what.