Dart vs 1000hp Supra heads up.

I had similar thoughts in that It would be nice to beat him "fair and square" ie by trying to be faster as opposed to making the other guy slower. but when the odds are stacked against you then it's reasonable to try to take advantage of the situation any way possible, especially for $500. (that's a lot of steak dinners)

Also they're probably going to be racing all day at an event like that, so it's not as if one quarter mile pass with a mischievous wager attached is the be-all and end-all of "who's faster" between the two.

As for OP being cocky. I gathered that's the nature of their friendship, they like to smack-talk each other and it raises the "pride" stakes which is what's really important to stay motivated towards being competitive and pissing off your mates for kicks.

As long as Darian in his Supra isn't offended I can't see any harm. (It's ok to be a little childish and stir the pot every now and then lol)

In Australia we have a saying "Settle, mate. we're not playing for sheep stations.."
which basically means it's only a game, life goes on if you lose.