Jason, your Buddy needs his own bike to ride. Holy crap!!!. I did see at a H-D dealer in Gruene had a sportster and attached was a sidecar. Her dog a golden retriever would just climb right in to the sidecar chill. She said she had been taking him riding everytime she goes out since he was a 5 month old puppy and he is 4-5 years old now. My only regret with my buddy is I started so late, but he catches on real fast. He still doesn't like the Doggle much, but treats are helping keep them on.