First money drop scene in men's bathroom... please explain

This is one of my favorite movies and I've watched it many, many times, but I've never been sure about that part, either.

My best guess is that those two guys were involved (either for each drop or just this one), and their role in this case was to make sure the coast was clear before Gloria went in.

Even though she was a paramedic and plausibly could have stated she was checking to make sure everyone was out, someone who was still behind in the mens' room (like Stark, if he'd decided to stay behind and confront her, as he told Arlo he was considering) might have questioned why she checked the mens' room when the two male paramedics did not.

It's possible she used different flunkies for each drop (recall the guy with the shaved head and earring on the back of the bus) so that if Stark ever stayed behind at a drop location he wouldn't see her coming to retrieve the cash, and wouldn't see the same intermediary faces if he tried to linger behind more than once to catch her.

The idea that Gloria might have widened the circle of those involved by hiring multiple associates, though, seems to go against the exceeding caution she usually showed.

no, it was just coincidences. sometimes people lock eyes and it means something, other time it doesnt mean anything. i have unconsciously locked eyes with someone by mistake myself. this movie does allow for coincidences.
the first guy didnt have a bag, no money
the second guy when he finally leaves the building with his bag open he pulls out a towel rather carelessly. zero knows the guy wouldnt not have done that and risk money falling out.

geotalker is right. The towel that the weird-looking guy pulls from his duffel bag eliminates him from suspicion as the blackmailer. If you listen to the DVD's commentary, Jake Kasdan explains this.

I admit, this is a bit confusing and hard to believe.

It was a little red herring. The two shady looking guys were just two random shady looking guys who happened to be using the gym when the money drop happened. He excludes them from being the blackmailers because when the guy with the duffle walks out, Zero sees him pull a towel from the bag, demonstrating that it's just his gym clothes and stuff.


"Unless Alpert's covered in bacon grease, I don't think Hugo can track anything."

They were just two gays cruising, like Al Pacino.