Say the hard things with clarity, kindness, and confidence.
AwkwardMessages helps you craft thoughtful texts for breakups, boundary setting, work requests, and every uncomfortable moment in between.
Live preview
"I value our friendship a lot, but I want to be honest that I don't feel a romantic connection. I hope we can keep things kind and respectful."
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Your options
Generated messages will appear here.
Instant options
Generate multiple message drafts in seconds, tuned to your tone and context.
Human sounding
No stiff templates. Just messages that feel like something you would actually send.
Privacy focused
We store only what is needed to improve the experience, with strict rate limits.
How it works
Describe the moment
Give a quick summary of the situation and what you want to say.
Pick your tone
Choose a tone that matches the relationship and the outcome you want.
Personalize and send
Select the best option, tweak it if needed, and send with confidence.
Popular templates
View allBreak Up Text Message Generator
Craft a clear, respectful break up text when you need to end a relationship over message.
Reject Someone Nicely
Say no to a romantic advance without being harsh or confusing.
Ask Someone Out
Invite someone on a date with confidence and respect.
Friend Zone Message
Set kind boundaries when you only want friendship.
Apologize to an Ex
Offer a sincere apology to an ex without reopening old wounds.
End a Situationship
Close a situationship with clarity and kindness.
FAQ
Is AwkwardMessages free to use?
Yes. The generator is free for personal use and includes built-in rate limiting to keep things fair.
Can I edit the messages?
Absolutely. We encourage you to personalize the draft so it sounds like you.
Do you store my messages?
Only minimal analytics are stored to improve the product. Sensitive details should be kept out of the prompt.
Ready to write the hard message?
Start with a prompt and get three human-sounding options in seconds.
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