A very complicated term meaning the way you're making a move on someone. This term finds its origin with cocky rep hockey and lacrosse players, who often think that their wheels are round, when indeed they are square. There are various ways to use said term.
a)describing how well your macking technique is working out for you. For example, one might say "square wheels" or "pentagon wheels" if the technique is not very effective; if the tactics are effective, however, one could say "wow, those wheels are so round right now!"
b)can also be used as a verb: "so, who are you wheelin' on these days?" Translation: "who are you trying to get with these days?"
c) can be used as an encouragement: "sick wheels man!" or a heads up that you need to reconsider: "whoah you're wheels are burnin' up, go take a lap!"
Disclaimer: As contributers to the honorable site urbandictionary.com, we recognize that not all hockey and lacrosse players are womanizing and have degrading conversations, we'll even admit that we like lots of them and are good friends... but hey, when describing their bunk language, what are we without our stereotypes.
a) Guy: "Did you just fart? Because girl, you just blew me away."
Girl: (awkward silence) ... yikes, octagonal wheels..." (walks away very quickly)
OR: Guy: "If beauty were time, you'd be an eternity"
Girl: "Ooohh, I like round wheels!" (walks away... with new boyfriend)
b)Hockey Player Number One: "Dude, check it, I'm wheelin' that blonde puck with the nice rack over there. Shotty."
Hockey Player Number Two: "Eassyyy herooo, take a lap; it's all about wheelin' on the younger grade eight girls these days, she's way too mature to fall for our corny pick up lines and empty promises."
c)Aforementioned Hockey Player Number Two walks by Hockey Player Number one and sees him hooking up with blonde bimbo puckfuckandchuck: "Maybe you do have some sick wheels broski! Nice!"
First Hockey Player extracts tongue from puckfuckandchuck's mouth and says: "yeah you better be jealous, this is what can happen if you oil those squeaky wheels of yours once in a while, you twat."