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  • Riddle: AI Advice & Journal screenshot 1
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About Riddle: AI Advice & Journal

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?

What’s new

Version 1.0.12 · Updated June 7, 2026

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.

App privacy

The developer, Nicholas Adams, reported these privacy practices to Apple.

Data Not Collected

The developer does not collect any data from this app.

Alternatives to Riddle: AI Advice & Journal

Looking for apps like Riddle: AI Advice & Journal? Here are 6 similar apps on the App Store. The highest rated is LoveWorkz: Relationship App (5.0/5), and all 6 are free to download.

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