I don't regret buying my road bike. I sort of regret buying my hybrid as I haven't ridden it since I bought the roadie, but even though it was an expensive "mistake," it's what started me on the road, so to speak, to cycling. I'm ready to find a new home for the hybrid though.
I agree that you should first determine what your cycling needs are and what kind of riding you want to do and where before buying a road bike. And once you decide to buy a road bike, I'd suggest investing some time and energy in learning about them, what options are out there, how to get fit on a road bike, etc. before plunking down any money.
K-
Live with intention. Walk to the edge. Listen hard. Practice wellness. Play with abandon. Laugh. Choose with no regret. Continue to learn. Appreciate your friends. Do what you love. Live as if this is all there is.
--Mary Anne Radmacher