Sometimes awkward situations just happen, like when your pants fall down, or a bridge you designed collapses, killing hundreds of people. It's kind of hard to lighten things up when you're taken by surprise like that.
But there's also a lot of awkward situations we anticipate, and have a little plan ready to defuse the tension. Unfortunately, a lot of those strategies end up making things even more awkward. Like ...
Letting Someone Else Go First
I'm not talking about holding doors open for people, which is its own nightmare of misunderstandings and mixed messages. I'm talking about situations like getting out of an elevator, where someone right up against the door should logically be the first person to get out (assuming it's everybody's floor). Instead, some polite folks, anticipating anarchy, step away from the door to hold the it open and let people out, which in a crowded elevator, makes the people they are backing into have to scramble to rearrange themselves.
A lot of times they're worried about awkward situations like the doors slamming on people getting out or closing before the next group has time to get in. Meanwhile, they've created an awkward situation as the people right behind them, ready to follow them out, halt confusedly while they watch this person rearrange themselves into the corner, and then try to figure out who should exit first in this new arrangement. Sure, it's just a few seconds, but you all could have just poured out like subway passengers and no one would have to spend any time feeling weird.
OK, I admit the subway is probably not the best place to go for examples of non-awkwardness.
And that's assuming there's only one chivalrous knight on the elevator. If two people have the same idea, they could end up in a brief "after you" standoff after everyone's exited.
Or sometimes you're about to turn onto a busy street (or cross one as a pedestrian), and you're just waiting for a gap in the cars when some nice driver slows down and waves you in. In many cases this is a nice thing, but in some situations it just makes everything worse. For example, if there's more than one lane going the same direction, and one guy in one lane tries to wave you in, while the drivers in the other lane don't give a shit and keep going. You can't turn until both lanes are stopped, so this nice driver is just holding up his entire lane and accomplishing nothing, and everyone behind him is now mad at him and you.
"Nobody else wants to stop!" you mouth at him silently, and he just keeps smiling and waving you in, like he doesn't see what the problem is. Man -- just go, dude. There will be a gap eventually, or maybe not, now that all the cars backed up behind you will be catching up where that gap was going to be.
Or how about stop signs, where some people disregard the fact there are clear rules about who goes first and consider it a chaotic Lord of the Flies situation where somebody has to take charge and they're willing to step up and start waving people through like they are the Stop Sign Lord. Confused drivers assume he will go first because he stopped first, but no, in his magnanimity he waves some random person through instead. This is not a complex situation that requires a level-headed leader to save the other drivers from chaos. You stop first, you go first. This is not hard to grasp. Oh, and blinking red traffic lights? Those are stop signs. Same rules. You're welcome.
Trying to "Include" the Shy Guy
Every "quiet person" knows that there are people out there that think this is a defect. If you're not talking very much at a party or gathering, something is obviously wrong with you. You must be mad, or a little slow, or intimidated by present company. Not talking much couldn't possibly be one of the many diverse personality traits people can have.
And there's no question that one silent person in a group of talkative people can make the situation a bit awkward. So some people's solution is to try to "include" them by making a joke about how quiet they are, which is probably the worst thing you could do to make them feel less awkward.
"Hey, you're not talking to anyone! HEY EVERYBODY SHE'S NOT TALKING TO ANYONE!"
Phrases like, "Jeff hasn't said a word!" or, "Oh, look, we're probably boring Jeff with our baseball talk. I bet he's not a baseball fan," or, "Jeff must think we're a bunch of crazy gossips, his ears are probably burning!" Or they might make a joke about how quiet the person is. If the group has been talking about their crazy drunken exploits, they might say winkingly, "I bet Jeff has some crazy stories. I bet he's a wild man at parties! He's got a secret side we don't know about! Ha ha ha!"
Moments later, tragedy struck.
Of course the quiet person, being a quiet person, is able to respond to these jokes awkwardly at best, so all you've done is put them on the spot and call attention to how quiet they've been all night to anyone who wasn't paying attention before.
Trying to include a person is a nice thing to do, but there are way more discreet ways to go about it than what is basically, "HEY, LOOK AT YOU, QUIET PERSON!" Just ask them some things about their job or pets or life in a low-key way and if there's anything they really seem interested in and connects to other people there, expand on it. Maybe treat them like a person who might have some regular interests, instead of like their quietness is the most important thing about them. Crazy, I know.
Checkout Stand Jokes
I'm a bad person, so every time someone has a "special problem" at the checkstand and holds up the line, I hate them. To be fair, some of these problems aren't their fault -- a barcode the system won't recognize, a coupon the staff wasn't trained how to process, having a stroke, etc. But whether they're stuck there because of an honest mistake or because they're trying to pay in antique pennies, there's a right way and a wrong way to deal with it.
"That's 15 quarters and ... is that a doubloon?"
First of all, if you're arguing about an expired or forged coupon, just give it up. You've been caught. Just be a gentleman about it and say, "Well played," to the cashier and tell him he is a formidable opponent, and then be on your way. If it's something you've really got to see to the bitter end, though, for God's sake do not try to lighten things up for the people in line by making an awful joke.
Do not tell the checker, "I guess it's free, then!" when you can't find a price tag. Do not make a joke about "computers these days" when your debit card keeps failing. Do not turn to the line and remark about kids and what can you do with them when you have to stop paying in order to have a talk with them about whether a Naruto pencil case counts as school supplies or whether they have to pay for it out of their allowance.
I think the kid should pay YOU for being allowed to bring that to school.
The people in line don't want to know that you are sorry for holding them up, they just want you to hurry up. It's natural to think that making jokes would help defuse tension, but in a situation where people kind of think it's your fault anyway, it makes it sound like you're not taking their annoyance seriously and trying to pass off your coupon-arguing delay as no big deal.
"Oh, I've forgotten my ticket! What an amusing adventure we'll have arguing about it!"
It also makes it seem like you're taking your sweet time. You'd probably be better off with no eye contact, grabbing things frantically and rushing, which at least gives the impression you're trying to fix things and get out of there as fast as possible, which is way more appeasing to an impatient shopper than a corny joke.
Finally, the checker has probably heard those same exact jokes about a hundred times and is liable to stab you with a pen. Now that would be awkward.