Back in March my roommate and I had this whole spreadsheet system for splitting utilities, but she kept 'forgetting' to update her part for the internet bill. Eventually I just sent a Venmo request with a note that said 'hey, the $87 for March and April.' It sat there unread until September. What finally fixed it was switching to a shared prepaid card we both load at the start of each month. Has anyone else had a request just rot in limbo for that long, or did I just have a uniquely patient roommate?
The "$87 for March and April" part got me. I once had a guy owe me $40 for a parking ticket from a concert we went to together. He finally paid me back two years later, but only because his mom saw my mom at a wedding and asked about it. By then I'd already mentally written it off as a tax on our friendship.