Account for the relationship as it is now
Use a tone that fits the present relationship, not the closeness, authority, or access that existed in the past. For a message about how to ask a roommate to pay overdue utilities, use this factual base: list the amount, date, reason, receipt, prior agreement, and any part that remains genuinely disputed.
Ask without assigning an obligation
Explain what you hope for while making decline, delay, or a different format genuinely acceptable. Propose a payment, refund, evidence exchange, or installment plan with dates both sides can assess. Make the immediate next step clear enough that the recipient can answer without reconstructing the entire history.
Keep the ending honest
Do not threaten public exposure, add invented fees, or treat hardship as proof of dishonesty. Use secure payment methods and qualified banking, consumer, legal, or fraud support when appropriate. Avoid future promises, guilt, flattery, or nostalgia that imply the recipient owes you access.