Have you ever lent a friend money for a coffee, a taxi ride, or a shared meal, only to find yourself waiting for the return of that cash? The question of when to ask for repayment and how small an amount is worth pursuing can be tricky. For some, even a small amount like $5 (£3.70) is worth a reminder, while others feel it's more awkward to ask for repayment on anything under $20 (£15). Henry Payne, a 21-year-old from New York, says he would request $8.50 but would not go below $8. He prefers to ask once and avoids following up, stating that doing so twice would feel "insane." He admits he sometimes forgets to repay others himself, but would rather absorb the cost than risk an awkward conversation. Kaz Jahanbini, 19, believes it's better not to wait and prefers to repay immediately when someone covers his expenses. He follows the rule of "keeping your wallet close but your friends closer." His friend Nouria, also a student, agrees that every dollar counts, but she only asks for repayment if the amount is over $10. A recent study found that 76% of Gen Z individuals who paid for group expenses were not fully repaid, and 55% said this led to tension or damaged relationships. In the UK, Betsie Brooke-Taylor, 19, says she would ask for repayment even on a small amount like £5, believing that "every little helps." She notes a cultural difference between the UK and the US, where she thinks Americans are more generous. She also points out that payment apps like Venmo, used by over 95 million people in the US, make settling small debts easier. In the UK, people often need to exchange account details, which can be less convenient. For Annika Violet, 19, the amount she would ask back depends on whether she consistently pays for her friend. If the friend is not reciprocating, she would request $5. Unlike many, Annika is not uncomfortable with money conversations and believes that true friends should repay debts. Her friend Hanako Stepper, however, finds asking for money awkward and has never followed up on a debt. Annika suggests that those who struggle to ask for money should "be brave and bold," as resistance might indicate a lack of friendship. Money expert Laura Pomfret notes that many people feel embarrassed about asking for repayment, especially in the UK, and advises not to dismiss small debts, emphasizing that the amount shouldn't matter if repayment is desired. She also suggests remembering past debts when paying for others in the future. Ella Feuille, 21, from New York, says she would consider asking for repayment around $15. If a larger amount was owed, she would ask three times before giving up, though she wouldn't forget about it. She has friends she knows will never repay her, so she prefers to pay for them directly. Her friend Katrina Dimingot agrees and prefers a system where they take turns paying for each other, avoiding the need to settle debts directly.