Inspiration
Dear: Stay in Touch is a quiet app for the people on your mind. Not a detailed personal CRM, not a gamified dashboard, just a small daily nudge to reach out and keep your garden watered. Dear also makes it easy to call or text right from the application (whether through Whatsapp or iMessage).
For OpenAI Build Week, I built Dear, Your Way because the words (or nudge) that help one person reach out may not help another. Some users prefer a calm prompt, some want warmth, clarity, or humor. The problem statement was: how do we customize the point of interaction that will best close the 'intention-action gap' that keeps some of us from reaching out to our closest friends among all the distractions of our daily lives.
What it does
Dear, Your Way (the new feature) lets people shape how Dear encourages them across four dimensions (aside from the preset voices).
- Warmth: Calm, Warm, or Tender
- Humor: Simple, Light, or Witty
- Directness: Gentle, Clear, or Bold
- Literary style: Plainspoken, Thoughtful, or Poetic
That choice carries through daily prompts, notifications, optional message openers, completion moments, and widget surfaces. Dear brings one name to mind. The person using Dear decides what happens next, and this new feature helps remove the friction in the user's intention-action gap.
How we built it
The Dear, Your Way feature is built in Swift and SwiftUI for iOS. It uses a deterministic, on-device copy composer so a selected mix stays coherent across the app without a runtime model call, account, backend, or cloud persistence.
We used several AI-assisted development tools during the broader Dear project. Cursor (various OpenAI, Anthropic, and Cursor models) supported earlier product and app development work. For this Build Week submission, Codex and GPT-5.6 were used specifically for product design, test-first architecture, implementation, review, accessibility and copy-safety checks, and release preparation. ChatGPT image generation supported original visual exploration for logos and feature materials.
Challenges we ran into
The challenge was making the feature feel like a real part of the broader application, not a settings toy. One thing that helped was having brand documents and other rules / memory files for the new Codex agents to analyze and learn before designing the specs.
We needed all 81 possible combinations to produce copy across each surface. We also had to preserve Dear’s existing narrators, keep the custom option English-only for this release (with a goal to localize the feature across the 14+ languages in the future), safely migrate stored widget data, and support Dynamic Type and VoiceOver. The biggest challenge here was making sure that we ran a thorough diagnostic ahead of the spec and made sure it was detailed enough to have agents follow thoroughly with stage gates and checkpoints as well as verification passes (on top of me actually testing).
What we learned
Voice matters most when it appears at the moment of action. Some users prefer the default 'Dear' voice, while others find it cheesy. We have iterated on different voices more for the novelty in the past, and I've learned the power of brainstorming on specific features starting with a problem statement (e.g., how do we make the nudges more impactful at closing the intention action gap?). This adaptable voice idea will take the Dear app from good to great just by subtly adjusting the voice per user.
What’s next
Dear, Your Way is integrated into the full Dear TestFlight build as a free option alongside Dear and Friendo. I am continuing to test the flow across onboarding, notifications, widgets, accessibility sizes, upgrade paths, and real-device installs. Long-term I plan to localize the feature across languages and continue to refine the feature through iteration.
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