Handle Holiday Money Issues With Tact

'Tis the season of awkward moments -- the unexpected gift from your new neighbor; a visit from co-workers' kids who are busy peddling wrapping paper cubicle-to-cubicle; holiday happy hour tabs gone wild, and all sorts of other uncomfortable scenarios involving money.

For tips on how to graciously handle delicate financial interactions during this heightened season of consumerism, I went to the etiquette experts at The Emily Post Institute. They (politely, of course) referred me to the manners maven's great-great-granddaughter, Lizzie Post, who last year penned a modern manners guide for twentysomethings, called How Do You Work This Life Thing?

The basic etiquette rules haven't changed much since Emily Post's day, even though the situations requiring tact have. The key is to be prepared, to be willing to pipe up -- and, says Lizzie, to be "never feeling forced into doing something you're uncomfortable with -- financially or otherwise."

"A lot of etiquette is about prevention. It is much more about making your life realistic and not being a pushover or a doormat for people," she says.

With that advice in mind, I floated a few common money-related scenarios and asked Lizzie to steer us toward the most considerate course of action.

The Unexpected Gift

Are you now expected to exchange gifts with this person for eternity?

Lizzie Post: A gift is a gift. It is a nice gesture. It is not something that has a forced reciprocation with it. The first and most important thing to do is enthusiastically thank the person for the gift. To just turn around and pull the, "Oh, oh, oh, I will get you something or I have something for you; I will bring it in tomorrow" actually takes down a notch the other person's gesture. We get so worried about making it up to someone else or leveling out the playing field that we forget that gifts are gifts for a reason. Then, you've got a choice to make -- you can get the person a gift or not. It's fine to thank the person and leave it at that. If you decide to give a gift, you'll likely establish a gift-giving tradition with this person, and you may not want to go that route. If you want to get them something in return, simply go get them the gift and give it to them at a different time.

Splitting the Check

How to enjoy a night on the town when you're on a salad-and-tap-water budget and everyone else orders steak and Merlot.

Lizzie Post: The best way to handle this is to head the whole thing off immediately by saying, "Tonight I really just feel like getting a salad. Let's do separate checks so it is easier on the waitress." If the check comes and it looks like everyone's going to split the bill evenly, that's your cue to say, "Hey, guys, you know what? I only ordered a salad, so here's what will cover my meal and tax and tip." That way, they know that you have covered all the bases and aren't trying to skip out on your fair share.

Too Many Parties, Too Few Paychecks

When suffering from obligation overload, it's perfectly OK to just say no -- at the office, and even to your best friend.

Lizzie Post: Prioritize. Choose the things that you need to be a part of and those that are really important to you. If, for instance, you are asked to be a bridesmaid or maid of honor and you are on a tight budget, tell the bride what you can afford to commit financially, and let her know that you understand if she might want someone else to do it. Tell her that you'll be with her in spirit no matter what. Maybe that means that you skip her engagement party, but you attend the bridal shower.

Handling Handout Requests

How to avoid feeling like a sitting-duck human ATM.

Lizzie Post: At the start of the year, decide how much you are able to contribute to things like office birthday party pools, charity drives, and Girl Scout cookie sales. That way you can say, "I am really sorry, but I have contributed what I can on donations this month." Or ask your company to set up a panhandling policy. Fliers above the water cooler can alert those who want to contribute and take the pressure off you. The bottom line is you have got to be responsible. It is OK to say no.

Picking Up the Tab

To treat or not to treat? The answer is in the phrasing.

Lizzie Post: It depends on how the invitation was phrased. If your boss says, "Hey, Katherine, do you want to come to Blimpie and grab a sandwich?" -- that is a casual ask. If he says, "Let's go to lunch to discuss work," that's a more formal ask, and he should pay for the lunch. If you're unsure of the intention behind the outing (is it a date, or are we going out just as friends?), you could say, "Sure, but could we stop at an ATM so I can get cash?" That gives the other person the opportunity to say, "Oh, no, I will cover it," or "Sure, no problem."

Rich Friend, Poor Friend

Stop salary disparity from putting your relationships on uneven footing.

Lizzie Post: Often I find that the person who doesn't make as much feels guiltier about not pitching in. But after a while, when one person is always picking up the tab, both may get too accustomed to the arrangement. If it is getting under your skin, no matter which side you are on, you need to have a conversation. Focus on the fact that your enjoyment comes from your time together, not the amount of money spent. Explain that you understand your friend's financial situation but that it would make you more comfortable if the relationship were a bit more even right now.

Fool.com columnist Ms. Dayana Yochim knows how to pass the salt and pepper (together), hail a cab while wearing heels, and properly set a table -- with all the knives facing the right way, even! She has updated her resume to highlight these important skills.