When close friends who have taken money from me are not returning, it becomes a dilemma whether to follow-up aggressively or mildly. Concern is not to let the friendship break. However, without follow-up proactively they don't pay too. Given this situation what can be done? Balancing the need to recover your money while preserving the friendship is indeed tricky. Here’s a structured approach to handle this dilemma: 1. Reflect on the Situation Assess the Relationship: Is this a one-time oversight, or a pattern of behavior? Consider their past reliability and your friendship’s depth. Evaluate the Amount: Is the money significant enough to impact you financially, or is it more about the principle? 2. Start with a Gentle Reminder Assume good intent (e.g., they may have forgotten or are facing temporary difficulties). Example: "Hey [Name], I hope you’re doing well! Just wanted to check if you could return the amount I lent you earlier. Let me know if there’s any issue...