Easily Knock Out. He gives detailed opinions on things like looks & personality quite often. So I can see him playing you up which is needed or dressing you down but you can play it off as a joke & make your crush laugh with it. I think Knock Out would bring out some good things about you, intentional or not.

 

Out of Prime Cliffjumper, Cybertron Wing Saber, G1 Springer, Animated Sunstorm or Armada Hotshot
but my first option is G1 Springer. Depends on what continuity, we are in.

 

I'm surprised nobody has stated the obvious choice, Swindle! Imagine him, especially TFA Swindle trying to be a wingman like a used car salesman.
"Look at this stunning 30-something-year-old stud, don't let his mileage fool you! That guy still has enough stamina to match that of a college frat boy, sans the less desirable personality traits! *If you know, you know, amiright?*
Best of all, he has PLENTY of disposable income, just look at that collection! He must spend hundreds of dollars a year on those plastic knick-knacks... imagine the amount of dough he'll spend on you?? ESPECIALLY if he can spend $100 on a 3rd Party figure without even flinching!"

 

Blaster

Tracks

Powerglide

Wheeljack

Seaspray

 

TF Prime Arcee might make for a good female wingman. I just got the impression from the show she might be that type, just never explored in the plot.

 

Decepticon: Skywarp, the better personality for the job from the Seeker Trine and he could bounce whenever he needs to.
Autobot: Mirage could be a wingman for someone unconfident. He's sophisticated, from the upper elite, I would imagine pretty smooth and could literally give advice help without anyone being the wiser.

I laughed far too loud at this.

 

Either Powerglide for his experience with women or even sea spray for the same reasons.

 

Smokescreen. He knows all the tricks. Plus, f them bitches, we hittin' the casino.