Jester

7.0easy start · #14of 25
in AI Dating Assistants

Free trialyes
Well documentedyes
Runs where you workno

Runs on iOS. Paid plans from $4.17/mo.

Jester is ranked #14 of 25 in AI dating assistants on The Geeks Club. It runs on iOS. A free trial is offered. Paid plans start at $4.17/mo.

Jester plans and pricing

All plans

Jesse Monthly $4.99/mo apps.apple.com · 9 Oct 2026

Jester Pro $9.99/mo apps.apple.com · 9 Oct 2026

Jester Max $19.99/mo apps.apple.com · 9 Oct 2026

Jester Yearly $49.99/yr apps.apple.com · 9 Oct 2026

Compared on AI dating assistants

Profile tools: Yes
Opener generation: Yes
Reply suggestions: Yes
Conversation feedback: Yes
Image input: Yes
Mobile app: Yes

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The record

Product: Jester is an AI keyboard that reads dating chats and drafts replies in the user's voice for one-tap pasting.
Screenshot input: The maker says Jester only sees what the user screenshots and that typing stays private.
App coverage: The maker lists iMessage, Hinge, Tinder, Bumble, Instagram, and anywhere the user types as places it works.
Keyboard workflow: The maker says Jester lives in the keyboard and works across dating apps, DMs, and text threads.
Conversation replies: The App Store listing says users can screenshot a conversation and get reply options written in their voice.
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.
Messaging integrations: The App Store listing says Jester lives in iMessage, WhatsApp, Signal, and Telegram.
AI model: The App Store listing says Jester is powered by Claude Opus 4.6 and remembers the person the user is talking to.
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.
Free access: The App Store version notes say the first screenshot read is free, and the listing advertises a free trial.
Trial duration: The App Store version notes describe a yearly plan with 3 days free.
Platform requirement: The App Store listing requires iOS 26.0 or later for iPhone and iPadOS 26.0 or later for iPad.
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.
Company location: The maker's Instagram page identifies San Francisco, California.
Price from: $4.17/mo

Where it ranks on The Geeks Club

Best AI Dating Assistants in 2026#14 of 25

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Sources

tryjester.com· checked 9 Oct 2026
apps.apple.com/us/app/jester-ai-rizz-keyboard/id675962· checked 9 Oct 2026
tryjester.com/instagram· checked 9 Oct 2026