ShouldI: Drunk Mode

Wake up proud of last night

$2.99 · Designed for iPad. Not verified for macOS.

New in v1.1 — Apple Watch app, real-time projected savings tracker, six new themes, and a fix for the 'lurking app picker' bug. Wake up proud. ShouldI is the friction layer between your sober self and your future drunk self. Pick the apps you'd regret using tonight. Your shopping apps, your dating apps, your finance apps, your ex's contact, your socials — and lock them down for the night. To unlock anything, you have to pass a quick challenge first. Math, balance, reaction time, typing. Easy when you're sharp. Honest about when you're not. WAKE UP PROUD OF LAST NIGHT • See exactly which apps you almost opened • Watch a live tracker of the money you didn't spend • Confirm you got home safe • Skip the morning-after regret WHAT GETS BLOCKED Choose your own list. Pick whole categories — Shopping, Food Delivery, Social, Finance, Gambling — or individual apps. Amazon. Sephora. Instagram. Coinbase. Your ex's contact. Whatever you'd regret tomorrow. PASS A CHALLENGE TO UNLOCK Six quick challenges that get harder when your reactions slow down: Math Blitz, Memory Sequence, Reaction Time, Precision Tap, Typing Test, Balance. Pre-calibrate with a sober run so the app knows what 'you at your best' looks like. GOT HOME SAFE One tap on your phone or Apple Watch lets your designated buddies know you made it. No more 3am 'are you home yet??' texts. NIGHT OUT MODE — ON YOUR WATCH Take the challenge on your wrist. Send the home-safe ping without unlocking your phone. The watch app is included. SIX THEMES Pick the vibe — Espresso Martini, Lip Gloss, Disco Ball, Y2K, Black Amex, or Rosé All Day. Each one rewrites the copy, sounds, and shield colors to match. AUTO-SCHEDULE Set 'Friday and Saturday, 9pm to 3am' once and the lock activates itself. PRIVACY FIRST ShouldI does not collect, store, or transmit any of your data. Everything stays on your device. No accounts, no logins, no servers, no analytics. The apps you block, the challenges you take, the buddies you save — all yours, on your phone. BUILT BY ONE PERSON Made for people who want to enjoy their night out AND wake up to a $0 Amazon order, an intact group chat, and the keys still in their bag. — ShouldI is not a medical device or a sobriety test. The challenges are casual mini-games, not clinical assessments. Never use ShouldI's challenge results to decide whether to drive or operate machinery. If you're struggling with substance use, please reach out: SAMHSA's National Helpline 1-800-662-HELP (4357), free and confidential, 24/7.

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The developer, colby dimaggio, 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 Not Collected

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    Information

    Seller
    • colby dimaggio
    Size
    • 2.8 MB
    Category
    • Health & Fitness
    Compatibility
    Requires iOS 26.2 or later.
    • iPhone
      Requires iOS 26.2 or later.
    • iPad
      Requires iPadOS 26.2 or later.
    • Mac
      Requires macOS 26.2 or later and a Mac with Apple M1 chip or later.
    • Apple Vision
      Requires visionOS 26.2 or later.
    • Apple Watch
      Requires watchOS 26.2 or later.
    Languages
    • English
    Age Rating
    13+
    • 13+
    • Learn More
    • Infrequent
      Alcohol, Tobacco, Drug Use or References

      Contains
      Health or Wellness Topics
    Copyright
    • © 2026 Colby DiMaggio
  • Developer Website
  • Privacy Policy

    • Supports

    • Family Sharing

      Up to six family members can use this app with Family Sharing enabled.