I may be wrong but I think he meant the blowup was unreasonable but not the information he was trying to convey.
I like Rubystreak’s idea, but add this: order some food to go and make them pay for a third of it.
At first you made it sound like a major unbalanced exchange was continually on going, but changed it to $100 a year. It’s not that big of a deal, because that would be like $8 a month.
Sorry if I made it seem like a major international crisis at first. I was upset.
I go out with these guys socially four, maybe six times a year, and I overpay 15-30 bucks a shot, which is 4-6 times I get pissed off at them. Last night, by carefully avoiding dinner, I thought I’d found a way to avoid getting pissed off, but I failed, and vented my frustrations here, which helped me think it through.
I don’t get hosed for $1 four to six times a year without getting pissed off about it. I don’t appreciate anyone taking advantage of me (which is what your “friends” are doing). If you don’t like it, stop participating in it - fairly simple.
ETA: If you do a 360 on them, you’ll be doing the same thing you’ve always done. If you mean a complete turn-around, that would be a 180. 
Yeah, but you’d get a nice range of behavior while he’s going through the 45-135 range, and then on the way back as well. Also: isn’t it funny how when you spin completely around, you make a 360, but a complete turn-around is something different?
I won’t speak for mswas, but my experience is that people who are assholes about money (unrepentant moochers, consistently poor tippers) tend to have other characteristics that make them undesirable as friends.
Among my closest friends, there is no one I don’t feel comfortable taking turns paying the check with, because I know we won’t screw each other over.
Looks like someone has been studying the “conversational geometry” chapter in Dogbert’s “Clues for the Clueless”.
This sounds very familiar.
If your boss isn’t a real stickler about receipts, why not just submit the amount you figure they owe you on your next expense report? 
I wonder whether there is some cultural factor here. I’ve never heard of anyone complaining about paying for what you ordered.
[nitpick]It won’t faze them.[/nitpick]
pseudotriton ruber ruber, you need to become a more assertive person, and start commanding a little respect. If these were just acquaintances that you could start to ignore, that would be one thing, but this is your boss. If you think that these are some kind of favor that will come back to pay off in the end, you’re dead wrong. You are a doormat. Doormats don’t get promoted. Doormats get the minimal raise during annual reviews. Doormats get the crappy jobs and the “I’m gonna need you to come in this weekend” speech.
Don’t be a dick about it, and definitely don’t do any of the passive aggressive nonsense like “forgetting” you wallet. Just conduct yourself with self respect, and be more assertive. When you say “separate checks”, make it a statement, not a conversation opener. When they make the old lady comments, make a quick joke or give Jodi’s “keeping track of your finances” excuse, but re-state that you are getting a separate check, and make it a statement. Don’t get dragged into a conversation of the why’s and who paid for what last week - that just sounds whiny. Just state your desire confidently and as if there’s no reason you owe anybody in the world an explanation for your desire for separate checks (because, news flash: you don’t!).
When you buy the movie tickets, don’t wait for them to offer cash out of the kindness of their hearts. Either hand 'em the tickets and say “these were $10 apiece, please”, or go for the “I bought the movies, dinner’s on you guys.” Again, make it a statement, which is done with eye contact and confident body language.
Honestly, this little social situation might be a blessing in disguise: it may be just the opportunity you need to practice some assertiveness with your boss and coworker outside of the office.
Wrong, I was talking about a futuristic weapons system. 
You haven’t been around here very long, have you?
Hmmm, either you mean “If you knew me, you’d know I’m assertive”, in which case, no, sorry, I don’t know you, and in this thread you come across as very, very unassertive. Not just in the story you tell, but in how you respond to some others’ suggestions.
Or, you mean “If you know me, you’d already know I’m not assertive. Duh!” If that’s the case, hey, that’s cool and all, but this is your boss here, and your lack of assertiveness could affect your career.
Let’s just say that I agree I’m being unassertive in this anecdote (for reasons you may not support, but which make sense to me) and have to hold back my natural assertiveness in the context of my larger career goals, which depend in part on support from these two colleagues. It simply struck me as funny to be told I need to be assertive–I think that’s the first time I’ve gotten that suggestion here. Though, in your defense, I have tried to suppress my assertiveness since you’ve been a member of the SDMB–I was having a joke that you’re in no position to get, and (having explained my little joke) I’ll apologize for having you on for the amusement of others.
This very post has qualified you for entry to the SDMB Wuss Hall of Fame.
I’m having trouble picturing what kind of career aspirations make you have to pay for your boss’ dinner and movie tickets instead of just politely declining the invitation.
That’s exactly what I’m going to do in the future–up until this point, I’d been holding out hope that this was simply an unfortunate series of coincidences, some uncharacterisitic poor behavior on their parts, forgetful on their part as to who paid more the few times, some concerns about me worrying too much about getting screwed out of petty sums–but I think it would be better just to decline future social engagements with these fellows from here on out.
As to the kind of aspirations–simply being in an environment where my friends continue to outnumber my detractors. So far, these guys are squarely in my camp at work, and it would short-sighted to alienate them because they lack a social grace or two. A sharper line between “work” and “going out to dinner with the guys” is pretty easy to achieve, as long as I remember that I really want to draw that line in the future.
Here’s what would bug me: is a lack of social grace, or is it that they know they can both sucker you for $10 each time you go out to dinner? Is it accidental or deliberate? The fact that you’ve brought it up and they’ve responded with the “old lady” comment makes me think that it’s deliberate. They are using you. It’s not lack of social graces, it’s chiseling. They’re schnorrers, as my dad would say. If the only way you can cope with this fact diplomatically is by not going out with them, so be it, but prepare yourself for comments about that, too.