Originally Posted by cpt. Howdy

I admit it, everytime I see someone on the road ahead of me, I absolutely have to pass them. It always starts with a bike silhouette in the distance that I MUST catch up to before they turn off. At this point it's pretty much a given that if they stay on the same street for long enough I will catch them, and I know deep down that it's an empty victory because they never even know I'm racing them until I'm about 10 feet behind them, with a huge momentum advantage.

Just the other day, I was going about 10 miles an hour, cruising, when some guy on a couple thousand dollar Cervelo or some other uber light race bike, fully kitted out, aero helmet, full 9 yards, flew past me without so much as a warning. He didn't get too close, but I couldn't stand the smug look I was imagining on his face.

I'm riding a slightly too big for me Giant Option, made of steel, with a rack and a milk crate full of work supplies, wearing khakis, sneakers, and a big baggy wind resistant coat.
I immediately gunned it. I caught up to him about 100 yards later, and decided to just draft for a while since he was going 26 MPH. He turned around looking for me. (He was on the right shoulder, and looked over his right shoulder, so I know he wasn't looking for traffic, he just wanted to see how far behind he had left me.) Imagine the look on his face when he saw I was stealing his draft about 1 bike length behind him> I looked over, and there were two people in a pickup that thought it was just as halarious as I did that I was on him. So as soon as he saw me, I said "You're pushing 30, keep it up, and overtook him, the whole time, doing whatever I could to not let on that my heart was about to explode.

I got lucky in beating him, because right after I passed him, he turned left. (Skipping across 2 lanes to do it.)

Never had a prouder moment in cycling or fitness. I still see him on my ride every now and then, but he's usually going perpendicular to me, so I don't get a chance to spank him again.