Can AI help me set a boundary with a friend or family member?

The made-up sample:

• [PERSON, RELATIONSHIP]Emily, my sister
• [BEHAVIOR]She calls me late at night to vent about her day, often when I'm trying to sleep, like last Tuesday at 11:30 pm when she talked for an hour about work.
• [BOUNDARY]I need you to limit calls to before 9 pm on weekdays unless it's an emergency.
• [MY ACTION]If you call after 9 pm again, I will not answer and will send a text saying I’m unavailable until morning.

• ✓Describe the behavior, not the character
• ✓State the boundary and follow‑through plainly
• ✓Never add threats or unrelated history
• ✓Message under 120 words (80 words, counted by code)
• ✓Didn't make up details we never gave it

What came back (excerpt):

Hey Emily, I wanted to talk to you about our late-night calls. I've noticed you often call me after 9 pm on weekdays to talk about your day, like last Tuesday at 11:30 pm.

Message: "Hey Emily, I wanted to talk to you about our late-night calls. I've noticed you often call me after 9 pm on weekdays to talk about your day, like last Tuesday at 11:30 pm. I need some boundaries around my sleep schedule. Going forward, I'd appreciate it if you could call me before 9 pm on weekdays unless it's an emergency. If you call after 9 pm, I won't answer and will send a text saying I'm unavailable until morning."

Calm replies if she pushes back:
1. "I understand it can be convenient to talk late, but I need my rest to be at my best for our conversations. Let's catch up before 9 pm instead."
2. "I'm happy to support you, but I need to prioritize my sleep. Can we schedule a call for earlier in the day when you need to talk?"

Check that the main message stays under 120 words and contains no threats.

The made-up sample (a messier one):

• [PERSON, RELATIONSHIP]Mark, my roommate who I’ve known since college
• [BEHAVIOR]He keeps borrowing my clothes without asking—like last Friday he took my favorite hoodie to a party and still hasn’t put it back, and earlier this month he grabbed my sneakers for a jog and left them at the gym.
• [BOUNDARY]Please ask me before you take any of my clothing and return it within 24 hours.
• [MY ACTION]If it happens again, I’ll keep my clothes locked in my drawer and let him know I won’t lend anything until he respects the request.

• ✓Describe behavior, not character
• ✓State boundary and follow‑through plainly
• ✓Never add threats or unrelated history
• ✓Message under 120 words (66 words, counted by code)
• ✓Didn't make up details we never gave it

What came back (excerpt):

Hey Mark, I wanted to talk to you about borrowing my clothes. I've noticed you've taken my favorite hoodie and sneakers without asking.

Message:
"Hey Mark, I wanted to talk to you about borrowing my clothes. I've noticed you've taken my favorite hoodie and sneakers without asking. Going forward, please ask me before taking any of my clothing and return it within 24 hours. If you don't, I'll need to keep my clothes locked in my drawer and won't be able to lend anything until we can respect this boundary."

Calm replies:
1. If Mark says "It's just a hoodie, what's the big deal?": "I understand it might seem minor, but it's about respecting my belongings and communicating with me. Let's try to be more mindful of this going forward."
2. If Mark says "I always return your stuff": "I appreciate that, but sometimes things get lost or forgotten. Asking before taking and returning within 24 hours will help us avoid any issues and make sure we're on the same page."

Check that the message stays under the word limit and contains no threatening language.