sporters vs. street bikes

I do believe that the bike should always match the bikers personality and taste. But there is a difference between riding a sportster and a street bike, as for me... i learned how to ride a Harley 250 and i did enjoy it, don't get me wrong! I personally did not choose this bike, it was given to me by the instructors because i was the smallest out of the group and that bike was the only one that was close enough to the ground. In the back of my head i couldn't help but notice that the guy who had his street bike was having a way better time riding his bike than I was. Could there be that much difference ??