Lisa Gerstner, a staff writer with Kiplinger's personal finance, has some practical advice for those uncomfortable money situations.
Awkward money moment number one: splitting the bill.
Gerstner says if it's for business or a birthday, split it evenly.
If you're with a familiar group of friends and they order more food and drinks than you then it is okay to ask the server for separate checks.
Awkward money moment number two: roommates.
Gerstner says the most important roommate rule is to create an agreement.
Roommates could share the grocery bill or label what belongs to whom, and they need make sure everyone keeps the punctuality of payments.
Awkward money moment number three: co-worker charity donations.
Gerstner says when it comes to giving to a charity your co-worker is promoting, saying no or giving less does not have to be awkward.
You don?t have to give a reason.
A polite "no" and telling the person you admire what they're doing and wish them luck is acceptable.
Awkward money moment number four: family loans.
Gerstner warns against big loans.
Awkward money moment number five: pan handlers.
Gerstner says consider giving to an organization that screens for neediness like a food bank.
Or give a pan handler a coupon to a local food chain so the person has a couple bucks to eat.
But no matter what the awkward money moment there is one final piece of advice.
"I think the polite thing to do is just say 'I'm sorry' if you don't want to, I think it's always important to be kind and polite to everyone," said Gerstner.