Dear Sage,

I’m a pretty generous person. If one of my friends is short on cash, I usually lend them some money. I’ve had trouble getting them to pay me back, though. How can I be assertive but friendly?

Sincerely, 

The Buck Stops Here

Dear Buck,

Sometimes, open wallets combined with open arms lead to one unintentionally becoming a doormat. While you’re being a good friend by helping others out in a pinch, don’t do so at the expense of your comfort.

First, what are your friends spending your money on? If it’s for something urgent, like medication, I understand your willingness. As their friend, you might feel a duty to assist them in these emergency situations. If your cash is being exchanged for their Long Island Iced Tea each week, however, it’s not fair to pay for them if they don’t return the favor.

Passive aggressive behavior may not be cool in everyday interactions, but situations like these deem them appropriate. Send your smartphone-happy friends a request for transfer of funds through Venmo or Chase QuickPay, depending on your bank account. They’re likely to be on their phone anyway, and nothing says “Pay me back, plzzzz” quite like an undying, buzzing push notification.