WinkPilot: AI Rizz Wingman

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