If Someone Owes You Money, It’s Okay To Just Ask

Be direct.


The other day my roommate, who is moving out in a couple weeks, texted me and asked in a very roundabout way if we could talk about the security deposit. The ask was couched in a lot of language that led me to believe that he felt bad about asking for something that he was certainly owed. I read the message, responded in kind and we resolved the matter about fifteen minutes later in the kitchen while I made peanut butter toast. I’m not faulting his approach — asking other people for money feels terrible because money is tricky and everyone hates it and loves it in equal measure. But if someone owes you money and you need that money, don’t be ashamed to just ask.

It feels bad — terrible, even — to ask someone for money they owe you because it seems personal when it really isn’t. Asking someone to pay you back makes you feel like a nag. Everyone has their personal dollar amounts of what is and isn’t okay to let slide. Buying your friend a beer at a bar one night and then ceaselessly hounding them feels petty. The best kind of friendships allow for an easy, loose understanding with regards to the $6 beer or some tacos and a bottle of water from the truck: if you have it at the time and they don’t, you get it and it’s fine. They will remember. They will get you back.

I spent years of my life being the person who, when asked to pay someone back, would fly into a strange passive-aggressive panic in response, out of pride. Yes, I knew I owed them money. Yes, maybe I had it, but more likely, maybe I didn’t. Telling someone that you don’t have the $40 you borrowed for the birthday dinner you both attended a month and a half ago feels very, very bad. “I’ll pay you when I get paid again,” I’d say, and they would sigh and nod and accept it because they were my friends. An increase in income and a better grip on my finances made it easier for me to pay people back withtout the histrionics, the heaved sighs, the hemming and hawing. But, when I have to ask someone to pay me what they owe me, I feel like a debt collector, bracing myself for impact, for the same reaction.

If someone owes you money — a lot of money, or a little, or maybe a medium amount — just ask them. Be upfront. Send them an email, a carrier pigeon, a text, a Venmo request, a bouquet of those big gold Mylar balloons with your request spelled out in kind. It’s okay to ask for what you’re owed. If you owe someone money and you need some extra time, tell them. Caginess will get you nowhere. Be honest. Just ask.

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