Although I've read some fanfics that suggest he likes the view.
In all of Kevin Smith's Jersey films (apart from Jersey Girl which, well, don't get me started), it is Silent Bob who comes in with timely advice or resolves the sometimes-corpse-f*****g conflict that the main character is going through. Let's have a rundown:
Clerks: He shows Dante that he is actually in love with his current girlfriend, and should not go chasing the one that got away. Mallrats: He plays the tape that gets Brody's main love rival out of the picture and into a jail cell for pedophilia. Chasing Amy: He explains to Holden McNeil that he shouldn't try to meet the sexual standards of his previously-experimental girlfriend, and should be happy with what he has now. Dogma: He kills Azrael with Cardinal Glick's driver, allowing the apostle, the muse, the last scion, and yes, Jay, to save the Universe.
Huh, he really does look at a surprising amount of shirtless dudes.
The only exception is Clerks 2. When asked what Dante and Randall should do about their predicament (Dante has found out he's about to father a child with his boss on the eve of leaving New Jersey forever with his girlfriend) he says, "I got nothin'." Oh. Well that just shits all over my theory.
Just kidding! Kevin Smith has admitted that in the original script, it was Silent Bob who suggested Dante and Randall reopen the Quick Stop as their own. He changed it at the suggestion of producer Scott Mosier, who rightly pointed out that it's always Silent Bob who solves this s**t! Thanks for f*****g up a streak, Scott.