Jester is an iOS AI keyboard that drafts replies to conversations from screenshots. Users can capture a chat, receive response options phrased in their voice, and paste a choice. The maker says the keyboard works across dating apps, direct messages, and text threads, naming iMessage, Hinge, Tinder, Bumble, Instagram, and other places where people type. The App Store listing also names WhatsApp, Signal, and Telegram, and describes help with openers, pickup lines, profile reviews, when to text back, and what to say after a date. In Instagram DMs, it can show three reply options and an Auto option. The listing says Jester uses Claude Opus 4.6 and remembers the person being discussed. The maker says the app sees only screenshots and keeps typing private; Apple's privacy information says identifiers may be used for tracking, and coarse location, phone number, and photos or videos may be collected for functionality. The first screenshot read is free, and a yearly plan has a three-day free trial. Plans include Jesse Monthly at 4.99 USD per month, Jester Pro at 9.99 USD per month, Jester Max at 19.99 USD per month, and Jester Yearly at 49.99 USD per year. The app requires iOS 26.0 or later for iPhone and iPadOS 26.0 or later for iPad.
Who it is for
Jester may suit iOS users seeking suggested replies, dating-chat coaching, or help with profile reviews. It requires iOS 26.0 or later on iPhone and iPadOS 26.0 or later on iPad.
What is good
- Generates reply options from conversation screenshots.
- Includes profile reviews and opener generation.
- Shows three reply options inside Instagram DMs.
- First screenshot read is free.
- Yearly plan includes a three-day free trial.
What to know first
- Requires iOS 26.0 or later on iPhone.
- Requires iPadOS 26.0 or later on iPad.
- Apple reports identifiers may be used for tracking.
- Apple reports some personal data may be collected for functionality.
Verdict
Jester combines screenshot-based reply suggestions with dating-chat coaching and keyboard access across listed messaging apps. Check the platform requirements and Apple's reported privacy practices before choosing a plan.
Jester plans and pricing
All plansCompared on AI dating assistants
- Profile tools
- Yes
- Opener generation
- Yes
- Reply suggestions
- Yes
- Conversation feedback
- Yes
- Image input
- Yes
- Mobile app
- Yes
