Can AI help me ask a friend to pay me back without making it awkward?
Yes. Give it the amount, what it was for and how you want to be paid, and it writes a friendly reminder you can send as is. It will not guilt-trip anyone or invent a deadline unless you give one.
01Why bot
- A kind money reminder follows a simple pattern: say what it is, state the amount, make paying easy. AI follows patterns well.
- It keeps the tone light, which is the hard part when you feel awkward about asking.
- It only knows what you tell it, so any deadline or payment detail has to come from you.
02The prompt
Replace everything in [BRACKETS] with your own details, then paste it into your AI app.
You are a calm friend who writes short, friendly texts that remind someone about money they owe, without drama or guilt. Friend's name: [NAME] Amount they owe: [AMOUNT] What it was for: [WHAT IT WAS FOR] How I want to be paid: [PAYMENT METHOD] Deadline (optional): [DATE, OR NONE] Tone: [CASUAL, WARM, OR DIRECT] Your task: write three different versions of a reminder text. Rules: - MUST keep each version under 60 words. - MUST state the exact amount and what it was for in each version. - MUST mention the payment method in each version. - NEVER threaten, shame or guilt-trip. NEVER suggest the friendship is at risk. - NEVER invent a deadline. If the deadline is NONE, do not mention a date. - If anything is missing, ask me up to 3 short questions first. - This is a message draft, not financial or legal advice. Format: Version 1, Version 2, Version 3, each on its own line starting with that label. Nothing else.
03Steps
- Write down the amount, what it was for and how you want to be paid.
- Fill in the brackets and paste the prompt into your AI app.
- Pick the version that sounds most like you and send it.
04What can go wrong
- If your friend already paid or disputes the amount, a reminder can sting. Check your records first.
- For a large amount, a text may not be enough. Keep records and consider a written agreement.
05What to use
06Our test run
One run with a made-up sample; a second run with a different sample is on the way. 0 of 1 passed every check.
The made-up sample:
[NAME]Jordan[AMOUNT]$45[WHAT IT WAS FOR]concert tickets for the indie show last Friday[PAYMENT METHOD]Venmo[DATE, OR NONE]NONE[CASUAL, WARM, OR DIRECT]WARM
- State exact amount and what it was for
- Mention payment method in each version
- Format with labels on separate lines only
- Version under 60 words (28 words, counted by code)
- Didn't make up details we never gave it
What came back (excerpt):
Version 1: Hey Jordan, just a heads up, you still owe me $45 for the indie show concert tickets last Friday, can you Venmo me when you get a chance?
Read the full answer
Version 1: Hey Jordan, just a heads up, you still owe me $45 for the indie show concert tickets last Friday, can you Venmo me when you get a chance? Version 2: Jordan, hope you're doing well! Still waiting on $45 for those concert tickets from last Friday, can you send it over via Venmo? Version 3: Hey Jordan, reminder that you owe me $45 for the concert tickets last Friday, whenever you can Venmo me would be great, thanks!
Ensure the concert tickets description includes "indie show" in every version.
How each run works: we fill the prompt with a made-up sample, run it once in Llama 3.3 70B, and GPT-OSS 120B grades the answer against the prompt's own rules. Word limits are counted by code, and every quote flagged as made up is checked against the full answer. Your results can differ. How we test.