Stretching Your Dollar: Awkward Money Moments

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COLUMBIA - How often have you found yourself in a sticky money situation. You know one of those times when you don't know what to do or say. Here are the professionals' answers for the next time you're in the middle of a "Do-I or don't I" moment.

This first situation comes up a lot. Does the guy always pay on the first date, even if he wasn't the one who asked? Officially, if the girl did the asking, she should do the paying. If a guy is really uncomfortable with that idea, split it on the first date.

"The clerk asks you 'together or separate?' and I'm sitting there like 'Ohhhh, it's not really a date and if I pay for her then it might seem like I'm making it that, what if we're not really trying to make it that, ya know?" Spencer Puchta, MU student said.

The same rule applies to a business lunch too.

"The awkward part comes in that they think that I'm trying to buy them, trying to buy their business via the lunch, and I say 'No, uh, I'm just paying for lunch' and that, that can be very awkward at times," Patrick Murphy, a salesperson, said.

Leslie Jett, an etiquette expert, said that heeding people's request when it comes to picking up the tab is sound advice.

"If someone says 'I've got the check,' you drop it. You never extend any aggression or push back at all. If someone says 'Hey, I've got this' let them have it. If it something that is really gonna bother you, you can leave the tip," Jett said.

Another one that comes up can be solved by the same go-to-line you've probably heard plenty of times... You break it, you buy it. It doesn't just apply to stores. If you accidently break something at someone else's house, you immediately offer to pay to fix it, or buy a replacement.

If it was crazy expensive or irreplaceable, insist the host pick something similar and then you pay for that, an apology note is also in order.

What about throwing a party when you expect others to pitch in? You've got to be up-front about how much you're asking for and considerate too.

"Do a little research about the menu, about the location you're going, and when you get there, make suggestions from the menu, based on your limits on hospitality," Jett said.

Never spring your intentions on guests during the event or afterwards. If you're too meek to ask for help beforehand it's your bill to pay.

And what about giving at the office? Weddings, baby showers, birthdays and retirements, it comes up all the time. In a perfect world of office politics you wouldn't have to worry about seeming cheap to your boss or co-workers. But practically, you kinda do need to pitch in.

If it comes up too often, talk to a supervisor about capping the cost or celebrating only certain events. He or she might be sick of getting hit up to contribute all of the time too.

5 tacky money moves:

1) Asking dinner guests to bring an appetizer or dessert. If they offer, great, if they don't, you're on your own to fill the evening's menu.

2) Making an invite a thinly disguised invoice. Requesting money in lieu of gifts? Is it a celebration or a shakedown?

3) Stalking people in the name of charity. You want someone to donate to a good cause sure. Mention it once and move on. If they don't give, get over it.

4) Asking how much a person makes. Unless you're an IRS agent, it's none of your business. No matter how close you think you are. If they want to share, they will.

5) Rubbing it in when you bail out a friend. Coming to you for cash is probably embarrassing enough. If you need to pat yourself on the back, do it in private.