What to do when it goes beyond pinching pennies.

Each product we feature has been independently selected and reviewed by our editorial team. If you make a purchase using the links included, we may earn commission.
Check With Cash
Credit: Garsya / Getty Images

Do you have a friend who's a total cheapskate? You know, the one who, when the dinner bill comes, won't actually reach for it, leaving you to pay. On this episode of “I Want to Like You,” Dr. Ted Klontz, behavioral consultant and co-founder of Your Mental Wealth and the Financial Psychology Institute (yourmentalwealth.com), and Jodi R.R. Smith, founder of Mannersmith Etiquette Consulting (mannersmith.com) and author of From Clueless to Class Act: Manners for the Modern Woman, join Real Simple Editor Kristin Van Ogtrop to talk about how to deal with the people who never seem to want to pay their fair share.

  1. Realize there’s a reason. Maybe your coworker grew up in a family with financial difficulties. Maybe your friend is paying off her student loans. There are a million reasons to be extremely frugal, Klontz says. However the main reason is (probably) not to irritate you.
  2. Address the Issue Without Calling Them Out. Klontz has a simple equation for why people seem to hit your nerves: unexpressed expectations = premeditated resentments. If you don’t clue the other person into how you expect them to act in the relationship, they will not be able to conform to those expectations–cementing your ill will. Smith suggests asking the waitress to split the check before you order. Or pick a less expensive restaurant to avoid problems all together.
  3. Include Them at the Beginning of Planning. As Klontz says, “You can’t spend other people’s money.” Even if you think someone can afford to chip in on a nice gift, know that looks can be deceiving, especially if you don’t know their story. Talk ahead of time to work out a budget.
  4. Let Go of What’s “Fair” or Ideal. If sending your parents on a nice vacation is a priority for you–but not others in your family–expect that you will have to deal with the brunt of the bill, even if it’s not ideal. But still let those who can’t equally contribute feel like they are participating–whether they pitch in a smaller amount or give their own add-on gift. Making everyone feel appreciated and understood lessens resentment on both sides.

Listen to the full episode below, and don't forget to subscribe to all of our podcasts on iTunes.