Yea. Chavy and desperate.
In my green youth I dated (VERY briefly) a guy like this. Always first in the line for freebies, would never pass a stand with those snacky bites in supermarkets to try and then circles back for another one, would queue for hours if it meant getting something for free even if he didn't need it (but it's FREE!), go to 'all you can eat' and pile the plate with random shit, eat even though he was bursting, etc.
In my defense I was about 16-17 when we dated (and it WAS brief). He was a few years older and had a job, though.
He would totally do what OP is suggesting and would pat himself on the back for being oh so clever and frugal.
Yuck. I'm frugal myself, but I'd be so embarrassed if someone who I'm with would do this.
Also, wtf's with actually PLANNING days/weeks in advance how to cheat the airport, secretly decanting wine, sending your children to get empty glasses, sneaking so the security/staff wouldn't catch you - that's all fine. But only drinking past 6pm? Well, gotta have SOME limits, I suppose.