Jester

What Jester is

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 a month, Jester Pro at $9.99 a month, Jester Max at $19.99 a month, and Jester Yearly at $49.99 a year. The app requires iOS 26.0 or later for iPhone and iPadOS 26.0 or later for iPad.

Who it suits

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.

Limits

The first screenshot read is free, and the yearly plan includes three free days. Continued use is covered by paid plans: Jesse Monthly is $4.99 a month, Jester Pro is $9.99 a month, Jester Max is $19.99 a month, and Jester Yearly is $49.99 a year.

Getting started

1. Open the Jester website
2. Install the iOS app from the App Store
3. Use an iPhone on iOS 26.0 or later or an iPad on iPadOS 26.0 or later
4. Allow Jester to work from the keyboard in your conversations
5. Use the free first screenshot read or start the advertised trial
6. Choose a monthly or yearly plan when needed

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.