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Published: Jun 08, 2017 5 min read
Michael Richards as “Cosmo Kramer” in SEINFELD
Castle Rock Entertainment—cour—©Castle Rock Entertainment/Courtesy Everett Collection

It was my friend’s idea to go out to eat.

We had just left her new apartment, which was still in that chaotic flux of flattened cardboard and freshly-moved furniture, and were on the lookout for dinner options her still-bare kitchen couldn’t provide.

I wanted something quick — pizza, falafel, grilled cheese — but was quickly cajoled into trying a new Cajun spot a few blocks away. A plate of crawfish and a few cocktails later, we decided to call it a night.

I can’t say exactly how we decided to split the bill, but what I do remember is paying the balance outright, with the expectation that she’d hit me back, with cash or through Venmo, shortly after. She never did.

For days, I contemplated bringing this up to her. But asking outright felt weird, and I didn’t want to embarrass her. Sending a Venmo notification didn’t seem right either. In the end, I let it go. The restaurant wasn’t terribly expensive, I reasoned, and frankly, I could use the good karma.

And then it happened again (bar tab).

And again (cab fare).

And again (friendsgiving).

I know what you're thinking, but let me be clear: This isn’t a case of Bad Friend Syndrome. In more ways than one, this woman is the most demonstrably generous person I know, and is quick to offer a ride, couch, or late night phone call long before you’d think to ask.

It’s not Pushoveritis, either. Chances are, you’ve also spotted a forgetful friend a time or two, opting to take the tiny hit to your wallet rather than face a potentially damaging conversation. It’s hard to pester people for money and for every freeloading friend, roommate, colleague, and sibling, there’s an over-obliging loved one who is spectacularly bad at it.

“What’s the harm?” we ask ourselves. We’re adults, with adult salaries. What’s $20? What’s $50?

Probably more than you realize.

“We tell ourselves that talking about these small things is going to feel bad, or awkward but that doesn’t mean you shouldn’t do it," says Shasta Nelson, relationship expert and author of Frientimacy. "Reminding a friend to pay you back doesn’t hurt a friendship -- resentment does. You don’t want to let this go."

The implications of a freeloading friendship go beyond the dynamic of our relationships, Nelson says. If we can’t hold our friends accountable, what chance do we have of advocating for ourselves when it really matters, like in salary negotiations or when asking for a raise? She suggests reframing how you approach these interactions; you’re not strong-arming a loved one into ponying up, you’re speaking up for yourself.

“We use these opportunities to build our muscles for asking what we need,” she says.

If you find yourself in a confusing, crawfish-and-cocktail-style situation, Nelson says it’s totally fine to send a reminder text or Venmo notification the next day. Maybe something along the lines of: “It was nice seeing you last night! When you get a chance, can you send that $20? Thank you so much.” If a few days go by and they still haven’t paid up, attach a deadline to it. "Hey, can you get my that $30 by the end of the day today? Let’s cross this off our to do list.”

In some cases, you can avoid any potential awkwardness with a little pre-planning, says therapist and relationship expert Melanie Ross Mills, PhD, (“Dr. Mel”) If you go out to eat with a habitual moocher, tell the server you’ll be splitting the bill before you order -- or vocally divide it up yourself when the check comes. Or, suss out the financial solution before you even meet up.

“Next time you go somewhere [together], ask ‘How much do you feel like spending?’ What’s your budget?’ Or ‘Let’s bring cash tonight,’" she suggests. “You’re organizing, not offending.”

There’s a caveat here, Ross Mills adds. It’s important to recognize the difference between a forgetful friend and a financial leech — if the mooch in question rejects your hints to pay his or her fair share, or is taking advantage of you in other ways (say, they’re constantly seeking your advice but are never reciprocating) you probably need to reevaluate your relationship.

Most of the time, though, a forgetful friend is just that.

“Life is busy, people forget things,” she says. “It’s your responsibility to remind them."