Cheap Night Out with a Corkage Fee
This one was inspired by some friends who recently did this exact thing, and had a hell of a night of food and wine out, so I couldn't help but share.
Say you are planning a dinner night out with friends, and you really don't want to have to deal with a big ticket at the end, mixing up a bunch of complicated drink orders, etc.
Look around for a place that allows a "corkage fee" option to bring your own wine. Find a decent boxed wine (I recommend aiming at least slightly above Franzia-level, but the point of this is to save a ton of money and have a fun night out, so you do you). An example might be the 3-liter box of Bota Box Redvolution, which is usually sub-$20.
For context, this was most recently used at a fantastic Chinese restaurant that allows you to bring your own wine, but charges a $10 corkage fee. We're not talking about a Chop House that might laugh you out for bringing in a box of wine, but I also would encourage the hell out of that if you can make it work. With any place, confirm nicely on the phone or in person that this place will let this pass as your "one bottle" of corkage fee.
Voila! You just got three (3!) full liters of dining out wine (~4 bottles worth - so enough for a huge table or a medium sized table of winos) for maybe $20 +$10 for a corkage fee, less than the price of a restaurant's cheapest "meh" wine option, typically.
Note: Anytime I recommend doing something to maximize your restaurant experience for a little cash as possible, throw on a very generous tip. Save some money and high five yourself mentally for gaming the system, but always share the love with the people bringing you food. It's just good practice.