Do what DaveBos did and get a long board, see these quite a bit on the promenade between Bournemouth and Boscombe especially at the Boscombe end where the road runs down to the roundabout by the pier, 30 odd year old teenagers come down the road and drift round the roundabout trailing a gloved hand on the tarmac, cool as fork!
I have always been rubbish on a skateboard but had a pair of inline skates back in my mid 40s and could skate backwards and do the big loops with a foot pointing in each direction but did have the excuse of trying to keep up with my two early teens lads, this was on the street, I wouldn't dare try it at a skate park or street without the kids present... bloddy peer pressure... and the potential threat of a restraining order these days.