I'd suggest you two guys ....shoot to establish a rolling average...( say a 200 target rolling average ) .....over 2 range sessions ( 100 birds a day)...
and then handicap eachother...
Avg ( 21 - 23 ) -- you get 1 bird
Avg ( 19-20 ) -- you get 2 birds
Avg ( 17-18 ) -- you get 3 birds..
Avg below 17 .../ you have to wear a sign on the back of your shooting vest..." I Suck at Skeet " ...
and with handicapps figured in now / over a 100 target day....loser pays $ 5 into a kitty ...for cold drinks afterwards.../ or lunch or whatever....give you something to "shoot" for ....and of course not to "wear" the sign...
and averages get re-calculated every 200 targets....so you don't get a disadvantage all day ..if you're improving...
Just trying to help ...