Names will be changed.
Here is the situation.

This is all in high school btw.

Me = Joe
Friend (needs help) = Bob
Friend (clueless one) = Will
Chick i was after = emily
Chick Bob was after = Kailey

So Joe and Bob have their eyes on these 2 HB7-8.5's that are always in a group of friends.
Joe and Bob resolve to take the opportunity to try and see if they can get the girls to approach them instead of the other way.

Everything is going well for Joe and Bob, girls seem interested, giving off all the right signals (smiling at you, staring at you when they think you aren't looking, making eye contact etc.,)

Then while Joe is going solo and testing to see how positive the feedback from emily is, Will comes out of nowhere and starts loudly talking about whether or not we should go to a club that night and have a contest to see who could pick up the most girls. WITHIN COMPLETE EARSHOT of Emily.

Result Emily thinks Joe is a stalker.

Bob now wants to go for it with Kailey.
Except Emily and Kailey probably think we're both stalkers

Bob wants advice.
I have never been in this situation before.

Any Advice for Bob?

You either need to school "Will" on how to behave, or cut him from the team when you go out. It's as simple as that. The relationship with the two girls you guys will working on will not be set based soley on what "Will" said, so long as you distanced your own viewpoints from his the moment he said it.

~Antithesis