Jester
Jester is an iOS AI keyboard for drafting replies to dating chats, direct messages, and text threads.
What Jester is
Jester is an iOS AI keyboard for drafting replies to dating chats, direct messages, and text threads. Users can screenshot a conversation and receive reply options written in their voice, then paste one with a tap. The maker lists iMessage, Hinge, Tinder, Bumble, Instagram, and other typing locations; the App Store listing also names WhatsApp, Signal, and Telegram. Coaching tools cover openers, pickup lines, profile reviews, when to text back, and what to say after a date. In Instagram DMs, version notes describe three reply choices and an Auto option that can answer for the user. The listing says Jester uses Claude Opus 4.6 and remembers the person being discussed. The maker says it sees only screenshots and keeps typing private, while Apple reports possible tracking of identifiers and collection of coarse location, phone number, and photos or videos for functionality. The first screenshot read is free, and a yearly plan includes a three-day trial. Plans are Jesse Monthly at $4.99 a month, Jester Pro at $9.99 a month, Jester Max at $19.99 a month, and Jester Yearly at $49.99 a year. It requires iOS 26.0 or later or iPadOS 26.0 or later.
Good
- Reply options written in the user’s voice
- Works across dating apps and messaging services
- Profile and opener coaching tools
- Free first screenshot read
- Monthly and yearly plans available
Watch out
- Requires iOS 26.0 or later
- Identifiers may be used for tracking
- Location, phone number, and media may be collected
- Auto can answer for the user
Who it suits
It suits iPhone and iPad users wanting AI-assisted dating replies, profile guidance, and conversation coaching. It is aimed at people comfortable providing screenshots and reviewing the app’s stated privacy practices.
Verdict
Jester combines a keyboard, screenshot-based reply drafting, and dating-conversation coaching on Apple devices. Review its data practices, operating-system requirement, and subscription choices before using it.
Plans and prices
From Jester's own pricing page, checked 9 Oct 2026.
| Plan | Price | What it gives you |
|---|---|---|
| Jesse Monthly | $4.99 a month | — |
| Jester Pro | $9.99 a month | — |
| Jester Max | $19.99 a month | — |
| Jester Yearly | $49.99 a year | — |
The facts
Each one read from Jester's own pages, with the date it was checked.
What it does
- AI model
- The App Store listing says Jester is powered by Claude Opus 4.6 and remembers the person the user is talking to.checked 9 Oct 2026
- Coaching features
- The App Store listing describes help with openers, pickup lines, profile reviews, when to text back, and what to say after a date.checked 9 Oct 2026
- Conversation replies
- The App Store listing says users can screenshot a conversation and get reply options written in their voice.checked 9 Oct 2026
- Instagram feature
- The App Store version notes say Jester can show three reply options inside Instagram DMs and that Auto can answer for the user.checked 9 Oct 2026
- Keyboard workflow
- The maker says Jester lives in the keyboard and works across dating apps, DMs, and text threads.checked 9 Oct 2026
- Messaging integrations
- The App Store listing says Jester lives in iMessage, WhatsApp, Signal, and Telegram.checked 9 Oct 2026
- Privacy practices
- Apple's listing says the developer reports identifiers may be used for tracking and that coarse location, phone number, and photos or videos may be collected for app functionality.checked 9 Oct 2026
- Product
- Jester is an AI keyboard that reads dating chats and drafts replies in the user's voice for one-tap pasting.checked 9 Oct 2026
- Screenshot input
- The maker says Jester only sees what the user screenshots and that typing stays private.checked 9 Oct 2026
Where it runs
- App coverage
- The maker lists iMessage, Hinge, Tinder, Bumble, Instagram, and anywhere the user types as places it works.checked 9 Oct 2026
- Platform requirement
- The App Store listing requires iOS 26.0 or later for iPhone and iPadOS 26.0 or later for iPad.checked 9 Oct 2026
The company
- Company location
- The maker's Instagram page identifies San Francisco, California.checked 9 Oct 2026
- Headquarters
- San Francisco, California, United Stateschecked 28 Sep 2026
Money
- Free access
- The App Store version notes say the first screenshot read is free, and the listing advertises a free trial.checked 9 Oct 2026
- Trial duration
- The App Store version notes describe a yearly plan with 3 days free.checked 9 Oct 2026
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