I once had a lad on a BMX try to race me in some Valleys town. I was going down a wide open hill on my road bike at about 40mph – he had no chance.. was all taken as a bit of fun tho by both of us 🙂
I also once played cat and mouse with a scooter two-up on the A48 towards Chepstow from Newport. It’s undulating, and the scooter was under powered so I reeled them in on the climbs and they got away on the descents. Kept pace for most of the way tho, although I was burying myself!