I have this trick that I employ at coffee shops and ice cream shops. I imagine it will work in other settings as well. First, the coffee shop technique.
I frequent a coffee shop (I'm actually there now) and despite the fact that their free coffee punch card requires 12 drinks before you get a freebie, and despite the fact that I order a $4+ drink every single time I go there, the permitted free coffee, is a simple cafe or decaf, beans seeped in water. Yep, coffee...plain coffee. This really irks me, and I recognize its due to my 1st world entitlement issues, but nevertheless, I use that fire to get more for my money.
I currently have a free coffee on my account, in fact I acquire them quite often. Yes, there is one thing I am NOT thrifty about, and its coffee. Anyways, so I approach the counter and give the cafe my customer name. They say - oh, it looks like you have a free coffee. And I say coyly, yeah but I can't use it for my mocha (frowny face). Tip: only use this trick when you don't recognize the person behind the counter, or if its a barista who is into customer appreciation or something. Then the barista, male or female, will reply, oh don't worry about that - I can do that for you. (Yeah, I kinda thought you could).
Next, when I go to ice cream shops, I offer a challenge to the person who is making my blizzard/freeze/flurry/whatever. I always ask for a small Reese's Peanut Butter Cup Flurry. Now usually you have to pay an additional cost for "extra stuff". I really got a kick out of it the first time I saw "extra stuff" on the menu, but hey, it's really a thing.
So I order my flurry, and I say, so... how much stuff do you really put in them? Is it just like a little or is it a lot - like a good flurry? (This works best by the way on a guy). To which he feels this pressure - like I'm giving him an opportunity to demonstrate his manhood. He can make me a kick ass flurry, which is a little bad-ass because there's probably a measurement, or something he really should be following. But no, he always takes the dare. He replies, oh yeah don't worry - I'll hook you up. Valah! Extra stuff, no extra cash.
At this point you're probably shaking your head a little, maybe you're embarrassed by my actions that are unequivocally born from a place of being a complete tight-wad . But honestly, this is who I am. And this is why I write.
For more coffee money-saving tips, be sure to check out my coffee category.