Now that I've got a nice bike, I've taken it out twice on two group rides. I found these groups through a neat website called MeetUp. It's a great way to meet new people and basically get out of the house. They have all sorts of things you can do.
Anyway, I did the first ride with Chris and Carey: the Winter Park Urban Assualt. It was a 20 mile ride going through the city. Damn, it kicked our asses. It was a high intensity ride, going through minor obstacles like curbs, stairs, rocks, and dirt, as well as plenty of evening traffic. Perhaps not the best choice for a first ride, but oh well. Luckily, it was a "no-drop" ride, so the advanced riders would wait for us to catch up when we fell behind. Towards the end, we were so tired, that we had to split off from the group and head back on our own.

The next ride was the Cady Way Trail social ride. It was a 18 mile trek on a bike path, at a much more leisurely pace. Chris and I did this, and it was definitely more our pace. We were tired at the end, but not completely destroyed like the previous ride. That, and the people on this ride were far more sociable than the Urban Assualt.
We'll probably do another Urban Assault again, although we'll just call it quits sooner this time around.