Wow, It's da Jackeeettt. I know exactly what scene you're describing, but I never picked up on Tony's deception to Jackie.

That was a big risk Tony took on by lying to the boss. But knowing Tony, he probably took into account that: a) Jackie was in the hopsital, and b) Tony could probably lie his way out of it to Jackie if ever caught (which was unlikely) by saying that Paulie & Silvio took Ariel away without Tony's knowledge.

I guess setting up Jackie to get laid was probably still a good-will gesture. But it was inadvertantly helpful to Tony since it happened immediately after Tony told his lie.