Riddle: AI Advice & Journal
Private Wisdom, Real Growth.
Free · Designed for iPad. Not verified for macOS.
Stop going to ChatGPT for relationship advice.
Riddle is a private AI companion that actually knows your story. It remembers your history, understands your patterns, and offers wise, balanced guidance — not generic sycophantic responses.
Your deepest thoughts deserve real privacy. Every message is end-to-end encrypted with a key only you hold. Not even we can read your content.
WHAT MAKES RIDDLE DIFFERENT
• Wise, not sycophantic — Responses are fair to you and the people in your life. Designed to calm anxiety and show you other perspectives.
• Deep memory — Riddle learns from your entire history, not just the last message. No more re-explaining context.
• Self-organizing topics — People, relationships, and themes organize themselves automatically.
• Voice journaling — Record voice memos as journal entries. Speak your mind, Riddle listens.
• Self-writing diary — A daily journal that writes itself from your conversations and reflections.
• Import your history — Bring your ChatGPT conversations so there's no cold start.
WHAT CAN YOU USE IT FOR?
Relationship advice. Personal growth. Journaling. Friendships, love, work — any relationship that matters to you. Give it your most vulnerable thoughts and watch them transform into insight.
PRIVACY BY DESIGN
Your data is encrypted on your device before it ever reaches our servers. We literally cannot read it. Your key, your secrets, your growth.
What's your riddle?
Ratings & Reviews
What's new in this version:
• Your journal now writes itself — Riddle turns your conversations into a reflective diary with its own illustrations (and a little haiku per entry). Entries are now saved so they're always there, and the journal loads much faster.
• Custom instructions — Tell Riddle how you want it to respond. Set your tone and preferences once in Settings and it remembers.
• Pin messages — Keep the responses that matter close, and find them again from the menu instead of scrolling back.
• Regenerate a reply — Not happy with an answer? Tap the refresh button on Riddle's latest message to get a fresh take.
• Max History — Tap "Max History" before a question and Riddle pulls in far more of your past conversations for that one answer — great for big-picture "what patterns do you see in me?" questions.
• Smarter responses — Upgraded to a sharper model with cleaner source citations and a longer memory of what you've shared.
• Rename yourself — Change the name Riddle calls you anytime in Settings.
• A redesigned side menu, smoother message ordering, plus bug fixes and polish throughout.
The developer, Nicholas Adams, indicated that the app’s privacy practices may include handling of data as described below. For more information, see the developer’s privacy policy .
Data Not Collected
The developer does not collect any data from this app.
Accessibility
The developer has not yet indicated which accessibility features this app supports. Learn More
Information
- Seller
- Nicholas Adams
- Size
- 38.5 MB
- Category
- Lifestyle
- Compatibility
Requires iOS 15.1 or later.
- iPhone
Requires iOS 15.1 or later. - iPad
Requires iPadOS 15.1 or later. - iPod touch
Requires iOS 15.1 or later. - Mac
Requires macOS 12.0 or later and a Mac with Apple M1 chip or later. - Apple Vision
Requires visionOS 1.0 or later.
- iPhone
- Languages
- English
- Age Rating
16+
- 16+
- Infrequent
Profanity or Crude Humor
Contains
Health or Wellness Topics
- Copyright
- © 2026 Nick Adams