# SideKey: Rizz Dating Assistant — AI Keyboard & Chat Wingman > AI keyboard wingman for confident and witty dating app conversations. (iPhone/iPad app by Olyndo Ltd.) - Source: https://appshunter.io/ios/app/sidekey-rizz-dating-assistant/id6754340912 (this page in markdown: same URL + `.md`) - Developer: [Olyndo Ltd](https://appshunter.io/developer/1833996613) - Category: Lifestyle, Productivity - Price: Free with in-app purchases - Rating: 5.00/5 from 1 App Store ratings - Age rating: 17+ - Requires: iOS 18.0 · 128 MB - Languages: English, French, German, Italian, Polish, Portuguese, Spanish, Turkish - Released: 2025-11-23 - Data updated: 2026-07-17 - Monetization: freemium - User reviews in markdown: https://appshunter.io/ios/app/sidekey-rizz-dating-assistant/id6754340912/reviews.md ## What is SideKey? Your screenshots → confident, witty replies. Instantly. SideKey is the AI Wingman that lives right inside your keyboard. Unlike generic AI apps, SideKey works directly where you text. Whether you're on Tinder, Hinge, Bumble, or iMessage — just switch keyboards, tap to scan, and get the perfect reply without ever leaving your conversation. No more overthinking. No more getting left on read. HOW IT WORKS Switch to the SideKey keyboard → screenshot the chat → tap scan. In seconds, you'll have a reply that sounds like you on your best day. It works where you already text — no switching apps, no copy-pasting. WHAT SIDEKEY CAN DO - Full-Context Replies: SideKey reads the entire conversation — not just the last message — so every reply actually makes sense and moves things forward. - Profile Icebreakers: Screenshot a match's bio or photos. SideKey spots their interests and crafts unique openers that start conversations strong. - Your Voice, Amplified: Choose your tone and goal — flirty, funny, chill, bold — so you always sound like yourself, just sharper. - Works Everywhere: Tinder, Hinge, Bumble, WhatsApp, Instagram, Snapchat, iMessage, and more. GO FURTHER WITH SIDEKEY PRO - Unlimited Replies & Scans: No daily caps. Analyze chats and profiles as much as you want, anytime. - Smarter AI: Unlock our most advanced models for deeper context, better humor, and replies that actually land. - Chat History: Review past conversations and strategies in the app to learn what works and refine your game. Dating is hard. Texting shouldn't be. Your Privacy Matters: - Privacy Policy: https://sidekey.app/privacy-policy.html - Terms of Use (EULA): https://sidekey.app/terms.html ## Key features - AI-powered keyboard for instant replies - Full-context conversation analysis - Profile icebreaker generation - Customizable reply tones (flirty, funny, chill) - Works across multiple dating and messaging apps - Unlimited replies and scans with Pro ## Pricing and in-app purchases Base price: Free. **Subscriptions** | Subscription | Price | Period | | --- | --- | --- | | SideKey Pro Yearly | $59.99 | per year | | SideKey Pro Weekly | $5.99 | per 7 days | | SideKey Pro Yearly | $59.99 | per year | | SideKey Pro Yearly | $59.99 | per year | | SideKey Pro Yearly | $39.99 | per year | | SideKey Pro Weekly | $5.99 | per 7 days | | SideKey Pro Monthly | $14.99 | per month | ## Frequently asked questions about SideKey ### How does SideKey help with dating conversations? SideKey acts as an AI wingman within your keyboard, analyzing conversations and profiles to suggest confident, witty, and contextually relevant replies. It helps craft icebreakers and ensures your messages sound like you on your best day. ### What dating apps does SideKey work with? SideKey is designed to work with a wide range of popular dating and messaging platforms, including Tinder, Hinge, Bumble, WhatsApp, Instagram, Snapchat, and iMessage, among others. ### Can I customize the tone of my replies with SideKey? Yes, SideKey allows you to choose your desired tone and goal for replies, such as flirty, funny, chill, or bold. This ensures that the AI-generated responses align with your personality and the context of the conversation. ### What are the benefits of SideKey Pro? SideKey Pro offers unlimited replies and scans without daily caps, access to smarter AI models for deeper context and better humor, and a chat history feature to review past conversations and refine your strategies. ### How much does SideKey Pro cost? SideKey Pro offers various subscription plans, including weekly at $5.99 (with a 3-day free trial), monthly at $14.99, and yearly options at $39.99 and $59.99. Pricing may vary based on the specific plan chosen. ### Is SideKey appropriate for all ages? SideKey has an age rating of 17+, indicating it is intended for mature audiences. This is likely due to the nature of dating app interactions and the AI's ability to generate potentially suggestive or adult-themed content. ### How often is SideKey updated? The latest version of SideKey is 1.2.8, and it was last updated on May 9, 2026. This indicates a relatively recent update, suggesting ongoing development and support for the application. ### Does SideKey have ads? Based on the provided data, SideKey does not have advertisements. The monetization model is freemium, with optional in-app purchases for the SideKey Pro subscription. ## Version history (last 5 releases) ### 1.2.10 — 2026-06-11 - Improve stability - Add support for Polish and Turkish ### 1.2.8 — 2026-05-09 - Improve stability ### 1.2.1 — 2026-03-19 - Improve stability ### 1.2.0 — 2026-02-21 - Improve Onboarding - Improve Coach feature - Add Chat Analysis from the app ### 1.1.4 — 2026-01-15 - Improve keyboard stability on iOS 26 ## Apps similar to SideKey | App | Rating | Price | Category | | --- | --- | --- | --- | | [CharmChat - Dating Assistant](https://appshunter.io/ios/app/charmchat-dating-assistant/id6463583958) | 4.8 (150) | Free | Lifestyle | | [WRizz: Rizz Keyboard](https://appshunter.io/ios/app/wrizz-rizz-keyboard/id6743861531) | 4.8 (2,083) | Free | Lifestyle | | [Lovia: AI Girlfriend & Flirt](https://appshunter.io/ios/app/lovia-ai-girlfriend-and-flirt/id6758355436) | — | Free | Lifestyle | | [Rizzler AI: Texting Wingman](https://appshunter.io/ios/app/rizzler-ai-texting-wingman/id6744320383) | 4.9 (71) | Free | Lifestyle | | [Flirta - Assistente de Paquera](https://appshunter.io/ios/app/flirta-assistente-de-paquera/id6744760246) | 4.8 (3,839) | Free | Lifestyle | | [Huzz AI: Ultimate Wingman](https://appshunter.io/ios/app/huzz-ai-ultimate-wingman/id6742404995) | 4.7 (1,263) | Free | Lifestyle | ## More apps by Olyndo Ltd - [Kaption: Video Captions](https://appshunter.io/ios/app/kaption-video-captions/id6751210694) - [Teleprompter - CreatorCue](https://appshunter.io/ios/app/teleprompter-creatorcue/id6751884613) - [Widget Studio: Custom Widgets](https://appshunter.io/ios/app/widget-studio-custom-widgets/id6757310906) - [HairKit: Hair Loss Tracker](https://appshunter.io/ios/app/hairkit-hair-loss-tracker/id6761551603) - [Sunly: UV Index & SPF Tracker](https://appshunter.io/ios/app/sunly-uv-index-and-spf-tracker/id6776840831) All apps by Olyndo Ltd: https://appshunter.io/developer/1833996613 --- *Data collected daily from the US App Store and indexed by [AppsHunter](https://appshunter.io/). User reviews are verbatim App Store reviews. Ratings, prices and chart positions refresh continuously; this snapshot is from 2026-07-17.*