I recently found myself in a tricky situation, torn between standing by my policy of not mixing business with pleasure and deviating away from it all together. My girlfriend called me earlier this week asking for a loan to pay off a debt, stating that she would rather owe me money than deal with the person she owed money. Giving her money as a loan felt like incorporating a business aspect into our relationship, something I am completely against. I had the option of just giving here the money and forgetting about it all together, but considering the amount, it felt like a very hard thing to do. It was a very awkward money situation.

Below are a couple of awkward money situations I came across on CNN Money plus an expert take on them. I figured I share a few of them, you never know, you might actually be dealing with one or two of them.

Awkward money situation number one:

Don’t you hate those parasitical family members who never pay for their share when you eat out together or go on vacation? How do you deal with them?

As Maggie Baker, psychologist and author of Crazy About Money puts it: you ought to be reasonable but firm. You could start by saying, “We’re happy that you’re coming but we need you to contribute financially like everyone else, or might there be some reason you can't?” Be quiet and wait for their response. Doing so will be disarming the person by letting him or her feel uncomfortable, plus you’ll be doing so in a mature way free of any sarcasm.

Awkward money situation number two:

How do you deal with a spouse who complains about no income but when it comes to financial tasks, complains of wanting to be involved in them?

Paula Levy, CPA and marriage and family therapists states that, “Having an input means that your spouse wants more information, not necessarily hands on work."

Awkward money situation number three:

This one actually affects me: how do you say no to a good friend asking for a loan, especially when you are not sure it will be paid back?

Andrea Bonior, clinical psychologist and author of “The Friendship Fix” advises that it’s ideal to give a response that doesn’t make it personal, you could say: “I’m sorry, but I’ve always had this rule not to lend money to friends,” or you could say “Hey, this has nothing to do with you, but I don’t lend money to friends.” It can be quite a challenging situation, especially when dealing with your significant other, but there’s no way around it.

Awkward money situation number four:

Have you ever had to deal with those co-workers who push you to buy stuff from them? They’ve come from Dubai with clothes and they are forcing you to promote their business, how do you deal with them?

Philip Galanes, advice columnist for the New York Times and auther of “Social Q’s” advises you to just say: “I hope you’ll understand, but I’m on a serious budget and trying to be disciplines about my expenditures.” Saying this once will save you from a life time of having to dodge your co-worker’s marketing strategies.

It can be difficult dealing with search awkward money situations, take me for instance, my girlfriend comes first, so I had to give her the money. I highly doubt that she will repay the loan.