WittyWingMan - Your AI Wingman

Upload chat screenshots and let WittyWingMan craft smart, personalized replies to keep your conversations lively.

For best results, use screenshots of chats with no user photos





Limited time: Get 5 credit FREE for signing up!

Our Unique Features

AI-Powered Conversation Starters

Our advanced AI crafts unique icebreakers based on your match's profile, ensuring endless engaging topics for more meaningful connections.

Personalized Reply Suggestions

Our app adapts to your chat style and match preferences for replies that truly sound like you, blending wit with authenticity thanks to smart machine learning.

Seamless User Experience

Dive into smooth, easy-to-navigate chats with our sleek app design. Perfect for AI newbies or tech enthusiasts, it helps you craft the right words quickly, turning chats into meaningful connections.

Real-Time Chat Analysis

Our app enhances conversations with real-time analysis, offering context-aware suggestions for timely and relevant replies, seamlessly blending with the natural flow of your chats.

Diverse Language Options

Connect across languages with our app's multilingual capabilities, offering witty replies in various tongues to enhance your conversations and expand your dating reach.

Discreet and Secure

Prioritizing your privacy, our app guarantees a secure and discreet chatting experience, protecting your conversations and personal data to let you focus on meaningful connections.

Tools to coach you online

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Dating App Openers

Engaging Conversation Starters for Making a Memorable First Impression on Dating Apps

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Message Replies

Crafting Thoughtful and Intriguing Responses to Keep the Conversation Flowing on Dating Apps

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Eliminate Small Talk

Bypassing Small Talk for Meaningful Conversations with Our AI App's Advanced Conversation Starters

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Natural IRL Intros

Mastering the Art of Natural and Authentic In-Person Introductions

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Natural IRL "Ask Outs"

Our AI App's Guide to Smooth and Genuine Approaches for Asking Someone Out in Person

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Break It Off Politely

Navigating Breakups with Respect and Tact Using Our AI App‘s Guidance for Polite Goodbyes

Get 5x More Replies

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3000 people have already tried WittyWingMan

Our happy users say about us

“I was always so nervous about what to say on dating apps, but this app changed everything for me. The suggested replies are incredibly on point and really sound like me! I've had more meaningful conversations in the last month than I've had in a year.”


Software Developer

“As someone who struggles with words, this app has been a lifesaver. The witty responses it generates have helped me break the ice and keep the conversation going. I've even secured a few dates, all thanks to this amazing tool!”


Senior Product Manager

“Never thought an app could so accurately capture my voice and humor, but here we are! It's like having a best friend give you chat advice. Plus, the privacy aspect makes me feel safe while flirting online.”


Senior Brand Manager

Simple, transparent pricing

Affordable plans for everyone


$2/10 Credits

A Helping Hand for Those Who Just Need a Nudge

  • Credits: 10
  • Tone: Not Supported
  • Reply Mode: Not Supported

Most popular


$7/40 Credits

Best for Maximizing Dating Success: Comprehensive Features for Enhanced Conversations and Improved Connection Outcomes

  • Credits: 40
  • Tone: All tones
  • Reply Mode: Supported


$9/100 Credits

Best for the Serious Dater: Premium Plan Offering All-Inclusive Features for Sustained Engagement and Optimal Dating Results

  • Credits: 100
  • Tone: All tones
  • Reply Mode: Supported

asked questions

We value privacy of every user which is why if the screenshot contains any personal information like phone number, email address or photo etc. we will not be able to generate a reply for that message. Try cropping the image to remove any personal information and try again.