Best Cheating Dating Apps

249+ iOS apps curated and reviewed

4.4 avg rating
19 free apps
Updated November 2026

If you already know DOWN, this is the deeper bench. 249+ cheating dating apps for iPhone, all reviewed and ranked by user rating, recency, and download trend as of November 2026.

Compare top Cheating Dating Apps (November 2026)

#AppPriceRatingAdsIn-App PurchasesUpdated
1DOWN: The Casual Dating AppDOWN: The Casual Dating AppFree4.3★ (132K)NoYesNov 2026
2Side Piece: Dating WingmanSide Piece: Dating WingmanFree5.0★ (5)YesYesOct 2026
3HUD™: Casual Dating AppHUD™: Casual Dating AppFree4.1★ (208K)NoYesNov 2026
4Ashley Madison Discreet DatingAshley Madison Discreet DatingFree4.1★ (79K)YesYesNov 2026
5Cougar Dating Adults SinglesCougar Dating Adults SinglesFree3.8★ (32K)NoYesNov 2026
63way: Couples & Singles Dating3way: Couples & Singles DatingFree4.6★ (32K)NoYesNov 2026
7Wild: Adult Casual Dating AppWild: Adult Casual Dating AppFree4.4★ (68K)NoYesNov 2026
83Fun: Couples & Singles Dating3Fun: Couples & Singles DatingFree4.4★ (151K)NoYesNov 2026

Top Picks for Cheating Dating

DOWN: The Casual Dating App#1

DOWN: The Casual Dating App by Down App, Inc.

Seeking a Meetup or Wild Date?
Editor's Choice
🌟 Lifestyle
4.3😐(132K ratings)
FreeIn-App Purchases
#15in Lifestyle
DOWN: The Casual Dating App screenshot 1
DOWN: The Casual Dating App screenshot 2
DOWN: The Casual Dating App screenshot 3
DOWN: The Casual Dating App screenshot 4
DOWN: The Casual Dating App screenshot 5
DOWN: The Casual Dating App screenshot 6

This app connects open-minded singles seeking various relationship types, from casual encounters to serious commitments. It prioritizes safety with photo verification and offers a straightforward matching system. Users can express their dating intentions clearly to find compatible matches nearby.

What We Love

  • 👍 Easy to use
  • 💡 Unique dating/hookup concept
  • 🚀 Smooth app performance
  • 🤝 Potential to meet new people

Room to Improve

  • 🐛 Buggy messaging and matching issues
  • 💰 Expensive subscription fees
  • 🤖 Concerns about fake/inactive profiles
  • 🌍 Difficulty finding local matches
Side Piece: Dating Wingman#2

Side Piece: Dating Wingman by William Rownd

Never Overthink Texts Again
Strong Contender
🌟 Lifestyle
5.0(5 ratings)
FreeAdsIn-App Purchases
Side Piece: Dating Wingman screenshot 1
Side Piece: Dating Wingman screenshot 2
Side Piece: Dating Wingman screenshot 3

This app provides AI-powered advice and reply suggestions for your text conversations. Upload screenshots of chats or dating profiles to get instant feedback and human-sounding responses to navigate tricky communication scenarios.

HUD™: Casual Dating App#3

HUD™: Casual Dating App by HUD STUDIO LIMITED

Meet Open-Minded Adult Singles
Worth Considering
🌟 Lifestyle
4.1😞(208K ratings)
FreeIn-App Purchases
#27in Lifestyle
HUD™: Casual Dating App screenshot 1
HUD™: Casual Dating App screenshot 2
HUD™: Casual Dating App screenshot 3
HUD™: Casual Dating App screenshot 4
HUD™: Casual Dating App screenshot 5
HUD™: Casual Dating App screenshot 6

This app connects open-minded adults for casual dating and exploring relationships on their own terms. It offers a safe, respectful, and transparent environment with features like video chat and photo sharing. Discover like-minded individuals for pressure-free connections and dates.

What We Love

  • 🚀 Clean and intuitive UI
  • 💡 Ability to set sexual preferences
  • 👍 Potential for finding hookups

Room to Improve

  • 🐛 Buggy messaging system
  • 💰 Expensive premium subscription
  • 🤖 Presence of fake/inactive profiles
  • 📍 Inaccurate location-based matching
  • 🔒 Unclear account suspension policies

More Cheating Dating apps to explore

FAQ about Cheating Dating

What are the best cheating dating apps for iPhone?
DOWN: The Casual Dating App tops our cheating dating apps ranking as of November 2026, with a 4.3-star average from 132K App Store ratings, and it's free to download.
Yes — 19 of the top cheating dating apps we rank are free to download, including DOWN: The Casual Dating App and Side Piece: Dating Wingman.
DOWN: The Casual Dating App has no ads and offers in-app purchases, according to its App Store listing as of November 2026.
We track 249+ cheating dating apps on the iOS App Store as of November 2026, ranked by rating, recency, and analysis of real user reviews.