WinkPilot: AI Rizz Wingman
Dating assistant, flirt texts
Only for iPhone
Free · In‑App Purchases
iPhone
5 free AI replies to start, no sign-up needed. Upload a screenshot of your chat and get a reply worth sending — in the tone you pick, in your language.
Upload a screenshot of the chat. Get a reply worth sending.
WinkPilot reads the conversation on your screen and writes the next message for you — in the tone you pick and in the language you use.
HOW IT WORKS
1. Upload up to 5 screenshots of one chat or one profile
2. WinkPilot reads them as a single conversation
3. Copy the suggested reply and send it
Screenshots are not the only way in: import a chat export or paste the conversation as text.
PICK YOUR TONE
Wink, Direct or Spicy — or type your own tone in your own words, like "sarcastic but warm". Not happy with a reply? Ask for another one in a different tone.
FIRST MESSAGE, NOT JUST REPLIES
Upload a screenshot of a profile instead of a chat and WinkPilot writes an opener built on what is actually in that profile.
AI REPORT
A report you can open on any message: compatibility, interest level, emotional tone, who invests more, red flags and advice. For a profile it reads differently — profile score, overall vibe and best traits.
IT KEEPS THE THREAD
Tell WinkPilot what they answered, and the next suggestion continues the same conversation instead of starting over. The context stays inside that one chat.
SOMETIMES THE BEST MOVE IS TO WAIT
When answering right now would work against you, WinkPilot says so and explains why — and still gives you something to send if you decide to reply anyway.
NOT ONLY DATING
Three modes with their own goals: Dating, Social and Work. Making friends, keeping a conversation alive, networking, following up with a client. Or describe your own situation in your own words and WinkPilot works to that.
IN YOUR LANGUAGE
The interface and the replies follow the language you choose, not the language of the person you copied the screenshot from.
FREE TO TRY
Every device gets 5 free AI replies. Real ones, generated for your actual conversation — not a demo. After that WinkPilot needs a subscription. No account and no email needed.
PRIVACY
Your chats are stored on your device. Screenshots are sent to our AI provider for analysis and are not kept on our servers.
SUBSCRIPTION
WinkPilot PRO is available as a weekly, monthly or yearly auto-renewable subscription. New subscribers start the weekly plan with a 3-day free trial. Payment is charged to your Apple Account at confirmation of purchase. The subscription renews automatically unless it is cancelled at least 24 hours before the end of the current period, and you can manage or cancel it any time in your Apple Account settings.
Terms of Use: https://winkpilot.com/terms
Privacy Policy: https://winkpilot.com/privacy
Ratings & Reviews
- This app hasn’t received enough ratings or reviews to display an overview.
The developer, Kirill Cheremkhin, 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 Linked to You
The following data may be collected and linked to your identity:
- Purchases
- User Content
- Identifiers
- Usage Data
Accessibility
The developer has not yet indicated which accessibility features this app supports. Learn More
Information
- Seller
- Kirill Cheremkhin
- Size
- 7.1 MB
- Category
- Lifestyle
- Compatibility
Requires iOS 18.0 or later.
- iPhone
Requires iOS 18.0 or later.
- iPhone
- Languages
- English
- Age Rating
16+
- 16+
- Frequent
Mature or Suggestive Themes
Infrequent
Profanity or Crude Humor
Alcohol, Tobacco, Drug Use or References
Sexual Content or Nudity
- In-App Purchases
Yes
- WinkPilot PRO — Yearly $79.99
- WinkPilot PRO — Monthly $19.99
- WinkPilot PRO — Weekly $7.99
- Copyright
- © 2026 Kirill Cheremkhin PR Novi Sad