DEAR HARRIETTE: My roommate is suffering from a tough personal loss that has left them completely overwhelmed by grief. I understand and want to give them the space and support they need to process, but because they were so preoccupied, they seem to have forgotten to pay their half of the rent. I didn't want to burden them, so I paid the full amount myself. When is the right time to ask them to pay me back? -- Awkward Timing
DEAR AWKWARD TIMING: You were kind to step in in the way you did, but know that your kindness was also risky. Even during tough times, people have to be responsible for themselves. Hopefully, your roommate will make good on paying their portion of the rent.
When do you say something? Now. Tell your roommate that you need to talk to them about something important. Be sure you have their full attention. Then note the day of the month that it is and that they missed making their rent payment. Tell them that you went ahead and paid it for them so that you two wouldn’t get a late fee. Mention that you know they were going through a hard time, but make it clear that you need to be reimbursed. Ask for them to write you a check, send the money electronically or go to an ATM to get you cash. Be insistent on getting the money right away. In this way, you will have handled your business. If your roommate needs more time to grieve, so be it, but you will have resolved this issue.