Your AI-Powered Dating Playbook
Play Your Cards
Choose from AI-generated reply cards like picking moves in a strategy game. Every response is a new play.
Dynamic AI Strategies
Top 3 choices tailored to the exact context and your unique tone. Every suggestion is dynamically labeled and ranked for maximum impact.
100% Private
Your chats never leave your device. Period. All processing happens locally — no cloud, no servers, no leaks.
Three Steps to Victory
Wingman Watches
Monitors your iMessage conversations in real-time, ready when you need it.
AI Deals Cards
Generates your top 3 ranked replies, each using a uniquely labeled strategy tailored to your intimacy level.
You Play
Pick your move, tap to send. Your conversation, your strategy, your win.
Watch the Connection Grow
Wingman AI's hybrid intimacy engine maps the emotional turning points of your relationship based on structural signals and romantic sentiment.
It Sounds Exactly Like You
Generic AI sounds like a therapist. Wingman AI analyzes your last 20 messages to extract your exact punctuation habits, laugh styles, and emoji preferences.
Raw Messages
> "no wayyy lol that's crazy"
> "im exhausted... wbu?"
> "wait seriously?? 😂"
> "ok im down, let's do 8"
Your Cards, Your Move
Hey! So I was thinking... maybe we could grab coffee sometime this week?
Haha okay but if we're doing coffee, I'm picking the place — I know a spot with the best oat milk lattes 😏
I'd really like that. Coffee sounds perfect — I know a quiet place downtown where we can actually talk.
Coffee sounds great! What kind of vibe are you feeling? Cozy bookstore or bright and bustling?
Built for macOS
Wingman AI isn't an untrusted cloud wrapper. It's a deep local integration built with Tauri and Rust. We analyze your chats purely on your device.
Native Overlay
A transparent, borderless widget floats seamlessly next to your iMessage desktop app. Zero friction.
Local SQLite
Analyzes the chat.db-wal file on your Mac directly. Your deeply personal chats are never sent to our servers.
Bring Your Own Key
Plug in your own OpenAI, DeepSeek, or Gemini key. Everything is stored cleanly and safely inside the macOS Keychain.
Ready to Play?
Join the waitlist and be first to try Wingman AI
No spam. Just your invite when we launch.