Comparison

What Should I Ask? vs Deep Deck

Price, ratings, monetisation and update history for both apps, side by side — with what reviewers say about each.

Head to head
About

What Should I Ask?

This app provides curated conversation starters to foster deeper connections. It offers prompts for various situations, from dating to self-reflection, helping users move beyond superficial small talk and spark meaningful dialogue.

Highlights
  • Curated conversation prompts
  • Categories for different moments
  • Distraction-free interface
  • Designed for meaningful dialogue
  • Icebreaker for gatherings
  • Self-reflection tool
Features
Read full description

Skip the Small Talk. Start the Connection. [NEW] Unlock our full library with Premium! Plus, stay tuned for our upcoming Play Mode—interactive games designed for your next hangout. Great conversations don’t happen by accident—they start with the right question. What Should I Ask? is your personal conversation companion, designed to turn "how was your day?" into "tell me the story of..." Whether you’re breaking the ice on a first date or deepening a lifelong friendship, we provide the spark. WHY USE WHAT SHOULD I ASK? Beyond the Surface: Curated prompts that bypass clichés and lead straight to meaningful stories. A Deck for Every Moment: Hand-crafted categories for First Dates, Late Night Vibes, Family Bonding, Team Building, and Self-Reflection. Zero Friction: A clean, distraction-free interface designed to be used during a conversation without taking you out of the moment. Spark Meaning, Not Awkwardness: Questions designed by experts to feel natural, curious, and safe. PERFECT FOR: Dating: Move past the "interview" phase and truly see someone. Friendships: Discover things you never knew about your closest friends. Self-Growth: Use it as a digital journal for your own morning reflections. Dinner Parties: The ultimate icebreaker for any gathering. Stop wondering what to say next. Download What Should I Ask? and start the conversations that matter. Privacy Policy: https://docs.google.com/document/d/e/2PACX-1vQ75H0603l-E7IehgufBndaTWdapvkuC1kzxs1OUdYUZB8Z9Frf-xOYEXWPJCOCJie8jp-CZY29qAnD/pub Terms of Use (EULA): https://www.apple.com/legal/internet-services/itunes/dev/stdeula/

About

Deep Deck

Features
Read full description

Deep Deck is a conversation app designed to help people move beyond small talk. It is built for real-life moments: a dinner with friends, a date, a long conversation with your partner, a meetup, or a meaningful catch-up with someone you care about. Instead of random questions, Deep Deck gives you curated decks with stronger themes, better prompts, and natural progression in depth. With Deep Deck, you can: • Explore thoughtfully designed conversation decks • Start with lighter prompts and go deeper when the moment feels right • Use it with couples, friends, groups, and communities • Enjoy a clean, focused experience on both iPhone and iPad • Unlock decks with one-time purchases, with no subscription required All decks are available for free with limited question preview that can be unlocked individually or through All Access. Deep Deck is built for people who want better conversations, stronger connection, and more intentional moments together.

Screenshots

What Should I Ask?4 screens
Deep Deck4 screens

Verdict

The call

The clearest difference is iOS requirement: What Should I Ask? at 15.1 against Deep Deck's 17.0. On price, ads, in-app purchases and device support there is nothing between them.

Scored on Price · Rating · Positive reviews · Number of ratings · Update frequency · Ads · In-app purchases · Monetization · Best chart rank · Devices · Requires iOS

CostPrice · In-app purchases · Ads · Monetization

Both are free to download. What Should I Ask? sells 2 in-app purchases, starting at $3.99 per month and Deep Deck sells 10 one-off in-app purchases. Whichever you choose, the download price is not the number that matters.

Scorecard1 real difference · 9 level
What Should I Ask? versus Deep Deck: the parameters behind the verdict, then further details
ParameterWhat Should I Ask?Deep Deck
PriceFreeFree
Rating5.0 (3 ratings) — better—
Positive reviews100.0% of reviews—
Number of ratings3 — better—
Update frequencyEvery 3 days—
AdsNoNo
In-app purchasesYesYes
MonetizationFreemium—
DevicesiPhone, iPad, iPod — betteriPhone, iPad
Requires iOS15.1 — better17.0
Further details — not scored
Size45 MB70 MB
Age rating9+4+
DeveloperJalen BellCedric Lignier

In-app purchases

2 purchases

What Should I Ask?

Subscriptions2
  • Premium Access - Monthly$3.991 Month
  • Premium Access - Yearly$19.991 Year
10 purchases

Deep Deck

One-time10
  • Longevity: Healthspan$4.99
  • Meaning & Purpose$4.99
  • Designing Your Life$4.99
Show 7 more
  • FIRE: Beyond Money$4.99
  • Die With Zero$4.99
  • Attention & Distraction Health$4.99
  • AI, Information & Power$4.99
  • Long-Term Travel & Connection$4.99
  • Create Your Own Deck Unlock$9.99
  • All Access Unlock$19.99

Questions

Is What Should I Ask? free?
What Should I Ask? is free to download, with in-app purchases available.
Is Deep Deck free?
Deep Deck is free to download, with in-app purchases available.
Do What Should I Ask? or Deep Deck have ads?
Neither What Should I Ask? nor Deep Deck shows ads.

Other comparisons