Not sure if I should approach a friend (26M) and his sister (24M) who owe me (26M) money

I’ve been best friends with Jake (26M) since middle school.

Over Christmas, me, Jake, and his sister Anita (24F) went on a socially-distant trip to a desert location, partially to help Jake recover from a divorce. I work in the travel industry so Jake and Anita relied on me to find fun activities and to make bookings for accommodations. I was able to fly Jake to and from this trip for free. Jake and Anita have a bit more of an upscale taste so I had to find pricier Airbnb’s which I vetted through them and double checked that they were okay with price-wise. I put in the associated expenses for anything pre-booked into an app called Splitwise and sent them the link which they joined so they could track their budgets. They had booked the car so they put that in the app.

The trip went well. A few days later I messaged that I had put in all my expenses into Splitwise and let them know they had incorrectly entered in some of their expenses to their detriment (they undercharged me for some items). On net they owe me a combined $2.3K. A week or two later I messaged Jake on MLK weekend and asked him to close out Splitwise to get it done with, which he said he would. He never did and now it’s practically February.

Anita’s wedding is coming up in late March and Jake also has other financial family obligations which may make him short on cash temporarily. A friend advised that I wait to bring up the money in case Jake needs time to pay it back which I’m inclined to do due to our long and close friendship. I don’t need the money anytime soon.

However, it rubs me the wrong way that if he needed more time all he had to do was let me know. If he needed the money he should have been much more frugal over the trip as well. To add insult to injury, he wants me to keep him on my travel benefits without paying me back for a trip I planned for his benefit. He recently boasted he received a check for $15k from a side hustle and insisted he pay for dinner but hasn’t acknowledged the trip expenses. On the way back Anita also upgraded her economy seat to first class.

tl;dr a friend and his sister owe me money. They may need time to pay me back and I'm willing to temporarily not acknowledge it to help them save face. However, I feel they should be bringing up the issue themselves.

Submitted January 31, 2021 at 02:47PM by top_lurk https://ift.tt/2Yxx9be