We’ve all been there. Our friend owes us $300 and we can’t figure out if they forgot or if they are toxic. The good thing is there is a perfect way to ask to get complete closure.
The next time you are in person together, have a text pre-written that you can send before entering the building. This allows you to confirm your friend is there and reads the text. If they get up and walk out, you have your answer that they are toxic before you even meet.
The text should read: “Hey, I just wanted to say I am so excited to see you and glad you are my friend. Something has been on my mind. From my perspective, you owe me $300 from XYZ, and I’d like to figure out when we can get that closed out.”
Once you meet, you can tell your friend you know this is awkward, but what did they think of the text? Sometimes there are elements of disagreement you didn't realize.
I don’t recommend keeping toxic friends, but if you want to keep the friend regardless of whether they pay you back, you can simply say:
“Hey, I just wanted to say I am so excited to see you and glad you are my friend. Something has been on my mind. From my perspective, you owe me $300 from XYZ. This is the last time I will ask you about it, but just know I will not be willing to loan you money again if we don’t get this paid back by the end of this month.”