I used to play table tennis against my grandfather when I was in my mid teens (he was on the young side). At first, I needed a 15 point head start for it to be close (first to 21). After playing every day for a couple of months we started on equal terms and I only mostly lost.

That was fun! I learned and improved but also every point I won was a victory. Had I played against a professional I'd probably never have won a point, never have got better, and quickly got disheartened. There is just a limit past which the skill gap stops things being fun imo