Be upfront about why you’re asking.
They're more likely to give you money if you explain what it’s for. Since you know this person well enough to have their phone number, they’re probably a friend, coworker, or family member, right? These folks are likely to be sympathetic to your situation. Briefly explain why you need the money and what you’re spending it on. For example: "Hey Vic! I hate to ask, but I’m in a bind. My energy bill is due Friday and I don’t get paid until the 30th." "Hi Uncle Phil! I didn’t budget enough money this month for my textbooks and school starts next week. Can you help me out?" "Lukas! So this is so embarrassing—I just finished eating at a restaurant and when I went to pay, I realized I left my wallet at home. Can you Venmo a few bucks?"
Specify how much money you need.
If you're vague, they may think you’re taking advantage of them. Don’t beat around the bush! If you ask them for “some money” or vaguely say “it’s for rent” without noting an exact sum, they’ll probably feel like you’re trying to milk them for a handout. And if they have to ask, “Well, how much do you need?” you can be sure they’re cringing! Specifying the amount makes this easier for both of you. You might say: "My rent this month is $875 and I’m $200 short." "I just need $20 to cover this meal and I’m good!" "The cashier said the total for my textbooks is $134.24."
Tell them when you need the money.
Give them a deadline if it’s urgent or if you’re asking for a large sum. The more convenient you make this for them, the better! If you need to borrow more than a couple hundred bucks, try to give them some advance warning so they’ll have a chance to get the money together. If you need help paying a bill, let them know the due date. And if you literally need cash right now, make that very clear. A few examples for you: "Rent is due on the 1st, so I’d need the money in 2 weeks." "The due date on my bill is October 24th. Can you get me the money by then?" "This is urgent tbh—the waiter is literally asking me to pay the tab right now lol."
Suggest how to send you the money.
Don't force them to solve any additional problems for you! You’re already asking for money, so make this easy on them and just state the best way to get it to you. This depends on your specific situation, of course, but giving them more than one option is always good (if possible). If there’s only one option, though, be super clear about that. For example: "Can you Venmo the money now? Or give your CC to the cashier? She's standing right here." "Would you mind making the check out to Gaslight Square Apartments? That way, you can mail it directly to my landlord." "I can drop by and grab a $20 bill if you aren’t busy. I appreciate it!"
Note when you’ll pay them back.
They’re more likely to give you the money if you promise to repay it. If you're asking for a $100 or less from a family member or loved one, they may not be concerned about whether you pay them back. You should definitely still offer, though! If you’re asking for a significant amount of money, most people will feel more comfortable if you tell them exactly when they can expect repayment. You might say: "I get paid next Friday, so I can repay the $200 on that day." "I can't repay the full $1,000 in a lump sum, but I can do $100 every month until my debt is paid off." "Venmo the cash now and I’ll pay for your meal when we go to dinner this Sunday!"
Put it in writing if you’re asking for a large sum.
Draft a document that details your repayment plan to put them at ease. Asking for a large amount of money can be pretty awkward, especially if you know it's going to take a while to pay it all back. You can reduce the weirdness by offering to draw up a payment plan, complete with due dates and installment amounts. For example: "I get paid every other Friday, so I can send you $100 via PayPal every time I get paid. I'll pay the first installment next Friday. If we stay on that schedule, you'll be repaid in full by Feb 24. Does that work?" Since you’re requesting money via text, tell them you’ll email the document to them in a few minutes. They can look it over and agree before sending money.
Drop some hints first if they owe you money.
Try this if your friend owes you and you'd rather not confront them. Asking a friend to pay you back is a bit awkward! If the day they promised to pay you back has already passed, try to give your friend the benefit of the doubt (maybe they forgot). Before making demands, try dropping a few hints like: "I can’t come out to the club tonight, tbh. I’m totally broke." "My rent is due next week and I’m short. What should I do?"
Be calm and direct if you need to be paid immediately.
Explaining the urgency can soften the request a bit. Even if you're super annoyed with your friend at this point, demanding “I need that $50 you owe me and I need it now!” is probably not the best way to go. Try a calmer approach so your friend feels sympathetic to your situation. For example: "I’m sorry to ask, but I really need the $50 you owe me so I can pay my CC bill. It’s due in a week..." "Can you help ya girl out? My car note is due on Friday and I’m short. If you can repay that $100 you owe, I’ll be able to pay my note on time. :)" To be direct without actually having to confront them, send them a money request via PayPal. That might do the trick!
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