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Dining with your boss can be nerve-racking enough. But now the check has arrived and it’s just sitting on the table. What do you do?

Reaching — or not reaching — for the check isn’t the only financial faux pas you can make at work. From group gifts to charitable fundraisers, there are a host of potentially awkward money situations that can crop up at the office.

Should the boss always pay?

Here’s the general rule of thumb: If you did the inviting, you should pay.

That means if the boss asks everyone to lunch to discuss the latest quarter’s results, the boss should pick up the tab.

However, if you’re the one who invites your manager to coffee to discuss a challenge on a big project, you should be prepared to pay (but don’t be surprised if the manager still insists on paying).

If your manager does reach for the bill, be gracious, but there’s no need to insist on paying. “When we protest too much, it can send the wrong message…and that can be seen as a power struggle,” said Deanna Geddes, associate dean for graduate programs at Temple University’s Fox School of Business. =

If you are planning to foot the bill, make that clear to help mitigate any potential awkwardness when the bill arrives.

“When I host, I am going to do everything in my power to make it obvious to people,” said Jodi RR Smith, president of Mannersmith Etiquette Consulting. That can be as simple as saying: “This is my treat, please feel free to order anything you’d like” when sitting down at the table. Or order first at the coffee counter, and then tell the barista you are also paying for whoever is with you.

If you are the boss, and you’re going out with employees for a drink, Smith recommends you pick up the first round and then leave. “Because of the differential of power, you should leave and let the rest of the group relax. Even if you aren’t in the office, you can still feel like you are being watched.”

Group gifts: Can you pass?

It’s nice to celebrate life’s big moments with our colleagues: weddings, new babies, birthdays.

But that can get expensive, and not everyone wants to participate.

When it comes to group gifts and celebrations in the office, let people know contributing is an option.

If you are spearheading the collection, don’t pressure colleagues to open their wallets. Try saying something like: “We are planning on getting a gift for Susie. Would you like to contribute or would you like to recognize Susie on your own?,” suggested Kate Zabriskie, president of Business Training Works.

Sending an email with the gift giving plans and asking for a contribution is the low-pressure approach, she added. “As a general rule, the less confrontational, the better.”

And if you aren’t in the position or aren’t interested in contributing, it’s acceptable to say something like: “I already had separate plans for Susie, but thanks so much for coordinating this.”

If you’re planning on getting a group gift, make sure people are willing to contribute or wait until the funds are collected before purchasing the gift.

“If you want to go out and buy on your own, you have to be prepared to absorb the cost,” said Zabriskie.

Birthday parties can also be exhausting for colleagues, especially at bigger offices where it can feel like a never-ending parade of cake and singing.

“It gets to a point where it’s like: OK we’ve had enough cake,” said Diane Craig, president and founder of Corporate Class, a corporate coaching and training company.

She pointed to one company that solved the issue by giving each employee a set amount of money on their birthday to buy a treat for the staff to celebrate.

“It takes the burden off other people having to contribute and it can be fun,” she said.

Splitting the check

Going out for a meal with coworkers can be a nice escape from the office pressure — until the bill arrives and people want to evenly split the check when you only had water and a salad.

It is acceptable to ask for separate checks, but be proactive about.

Let your fellow diners know when sitting down that you would like separate checks, and also be sure to let the server know before ordering.

“The polite thing to do is to be sensitive to different needs and financial circumstances,” said Geddes.

If separate checks aren’t possible, suggest using a mobile payment service like Venmo, which can make it easy to pay for only your share of the bill.

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It’s great that all your co-workers want to make the world a better place by participating in a charitable run or walk or by selling Girl Scout cookies. But, after awhile, workers can suffer from fundraising fatigue.

While these solicitations are often well-intended, don’t assume your co-workers are going to be as excited for your charity as you are.

“It’s important when asking people to be philanthropic that there is an element of choice,” said Geddes. “Forced philanthropy is a problem in the workplace.”

Another option could be to ask for anonymous donations, noted Zabriskie. By creating an online fundraising page, employees would have the option to donate anonymously.

If you are being hit up to sponsor your co-worker’s race but don’t have the means, let them know it’s not in the budget. Tell them you have set a budget for your charitable giving for the year and have already allocated all your funds, suggested Craig.

Bosses and managers need to be especially careful when asking for donations from employees.

“There might be that fear that if they don’t make a contribution there might be something negative down the line,” said Geddes.

A better option is for managers to not solicit donations at all.