Oh Wow, this is Awkward: When Someone Owes You Money Asks to Borrow Money, Again.

It’s a sad reality, but for the most part, women are uncomfortable discussing money. Whether that be negotiating a raise or balancing one’s finances, so communicating the lack of funds or money owed can be downright dreadful. 

In this “Oh Wow, this is Awkward” Series, I will address uncomfortable money conversations and a strategy to handle them.

As always, merci beaucoup to everyone who voted on these topics via my Instagram poll.

If setting a friendly reminder for monies owed didn’t work, and your friend, relative, etc., have asked to borrow money again, it’s time to be firm.

While I won’t advise mes amies to say no because every situation/relationship is different, I will suggest keeping specific realities in mind before saying, oui.

You may never get (any of) your money back.

Only “loan” what you can afford never to be repaid. If you have to take money from your savings account or any prior financial commitments (bills) you have, do not put yourself in a compromising predicament by over-extending.

It’s a reason why they continue to ask you.

Perhaps it’s believed that you have a significant amount of money at your disposal. I use the word “believed” because unless you share your banking statements, no one knows how much money you have. Irrespective of what you; share on social media, what you wear, where you live or what you drive.

Are you the path of least resistance?

If you are the first person people call when they need money, more than likely, it is because you ask very few questions, I.e., making them feel less uncomfortable, or it is known/believed that your passive personality always results in the desired outcome, immediately.

Whatever the reason is, it is never okay for anyone to take advantage of your kindness or financial standing.

If saying “no” is challenging for you, try asking questions.

“What do you need this money for? Have you tried securing a loan from a financial institution? Are you confident you can repay me this loan in addition to the previous loan?”

And once the questions are asked, state frankly: “I do want to help you, but you must understand the position I’m now in.  I never received payment from the last time I lent money to you.”

Whether you decide to lend money again, discussing the previous balance is necessary.

Mes amies never feel obligated to continue to support anyone (who isn’t your dependent.) I do understand that they’re many variables in relationships regarding family and friends.

But someone constantly reminding you of your past or how much they did for you when you didn’t have it with the sole purpose of getting what they want is manipulative, and it is psychological abuse.

If setting boundaries are complicated for you, this will not be easy, but it is a conversation that must be had. Not only for your financial well-being but your mental health.

Have you ever been in the situation? What was the outcome?

For other blog in this series, click the links below:

Oh Wow this is Awkward- Expensive Event

Oh Wow this is Awkward- Splitting the Check

Ciao for now 💋


  1. stephaniexialing

    Oh Jessie, I know exactly how awkward is. I have a friend who is always owing me money. When I remind her, I feel like I am bothering her. This always happens because I’m always the activity planner. Any recommendations? Stop inviting?

    • That is such an awful feeling that I know too well, feeling as though you’re bothering the person who borrowed money from you. I’d say only invite her to events that won’t break (your) bank if you know that she won’t pay you back. Or try setting the parameters prior to officially inviting her. “I’m planning ____, and it costs about $___, are you interested in booking tickets/reserving a spot?” I hope this helps my dear ❤

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