Comparison

Inside Then Out vs Dating Conversations

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

Head to head
About

Inside Then Out

This app helps you reflect on your life through guided or freeform journaling. Capture memories with photos, videos, and audio, track your goals, and monitor your emotional progress. It offers daily prompts, reminders, and a blog for wellness advice.

Highlights
  • Guided and freeform journaling
  • Multimedia memory capture (photos, video, audio)
  • Mood assessment and goal setting
  • Journaling streaks and rewards
  • Daily reminders and notifications
  • Wellness blog and advice
  • Passcode, Touch ID, and Face ID protection
Features
Read full description

We believe the best way forward is inward. With the Inside Then Out app, reflect on your life –past, present, and future. Capture your memories with pictures, videos, and audio recordings. Check in on yourself and your goals, and see just how far you’ve come. With our guided journals, you’ll never run out of things to say and opportunities to get to know yourself better. With our free-form journaling, you can let your own thoughts run as wild as you want them to! Get started journaling no matter your experience • Choose between a guided journaling experience, or a free, at-your-own-pace experience. • If you’re new at journaling, get inspired by thought-provoking prompts every day. • If you prefer to journal freely, create your own blank journals and write as you wish. Preserve your most cherished memories • Add photos and videos that tell your story in your journal entries. • Record your voice or your surroundings to add even more context. Make a commitment to yourself • Check-in with yourself every morning and evening with our mood assessment and goal setting tool. • Start a journaling streak and get rewarded with redeemable points daily. • Set a reminder and get daily notifications to encourage you to stay consistent. • Read more about wellness, and get advice you didn’t know you needed in our ‘Blogs’ section. Look back on your personal journey • Browse through your past entries using our calendar view to reflect on key moments in your life. • Get an overview of how your feelings have evolved over time using our check-in tool. Find the right tools for you • Shop all ITO products in app, with an easy checkout process and the option to redeem points you’ve earned! Your thoughts made private • Protect your journal with your device passcode, Touch ID, or Face ID. Multi-Language Support • We now support English, Spanish, French, Portuguese, Arabic, Hindi, and Chinese! Terms of Use: https://www.apple.com/legal/internet-services/itunes/dev/stdeula/

About

Dating Conversations

Features
Read full description

Great couples aren't born knowing each other — they ask. Dating Conversations turns your phone into a deck of 800 conversation cards, built to carry you from a slightly awkward first date all the way to the deep end. Pass the phone across the table, read the card out loud, and both answer. That's the whole game. No rules, no winners — just the two of you actually talking. FOUR LEVELS, ONE JOURNEY • Spark — light, easy icebreakers even a shy date can answer ("What's your go-to karaoke song?") • Connect — memories, dreams, favorites, and the stories behind them • Deepen — values, fears, and the questions you don't get asked at parties • Us — for couples who are official: your story, your future, how you love START LIGHT OR GO ALL IN The Full Date deals a perfect arc for one evening: three light cards, two closer, one deep, one about the two of you. Or pick a single level and go as long as you like. The app gently suggests going deeper as you answer more together — but nothing is ever locked. IT REMEMBERS SO YOU DON'T Ever pulled a question card you'd already answered? Dating Conversations keeps a history for each person you play with, so you never get the same question twice with the same partner. New relationship? Fresh deck, all 800. MADE FOR THE MOMENT • Favorite the questions that led somewhere good • Bookmark a card to come back to at the end of the night • Add a private note so you remember their answer ("dream trip: Japan") • Pick up right where you left off if the conversation runs long • Three looks: vivid Pop gradients, gallery-clean light, or bold ink black ACTUALLY PRIVATE No account. No sign-up. No analytics. No internet required. Your questions, answers, and notes never leave your phone — the App Store privacy label on this app says "Data Not Collected," and it means it. WORKS ANYWHERE YOU DATE Dinner table, road trip, park bench, or a video call when you're miles apart — one phone (or one screen share) is all it takes. 800 questions. Zero repeats. One good conversation at a time.

Screenshots

Inside Then Out4 screens
Dating Conversations4 screens

Verdict

The call

The clearest difference is in-app purchases: Dating Conversations at none against Inside Then Out's 4. Dating Conversations also leads on update cadence (every 5 days vs every 5 weeks). On price, ads, device support and iOS requirement 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. Inside Then Out sells 4 in-app purchases, starting at $2.99 per month. Dating Conversations asks for nothing beyond the download.

UpkeepUpdate frequency

Inside Then Out ships an update every 5 weeks, Dating Conversations every 5 days. The most recent releases landed on October 22, 2026 and October 12, 2026 respectively.

Scorecard2 real differences · 8 level
Inside Then Out versus Dating Conversations: the parameters behind the verdict, then further details
ParameterInside Then OutDating Conversations
PriceFreeFree
Rating3.5 (20 ratings) — better—
Positive reviews53.3% of reviews—
Number of ratings20 — better—
Update frequencyEvery 5 weeksEvery 5 days — better
AdsNoNo
In-app purchasesYesNo — better
MonetizationFree with in-app purchases—
DevicesiPhone, iPadiPhone, iPad
Requires iOS26.026.0
Further details — not scored
Size152 MB3 MB
Age rating4+9+
DeveloperInside Then Out, LLCScott GREER

In-app purchases

4 purchases

Inside Then Out

Subscriptions4
  • Better Every Day Journal7 Days trial$2.991 Month
  • Dig Deeper7 Days trial$2.991 Month
  • Better Every Day7 Days trial$19.991 Year
Show 1 more
  • Dig Deeper7 Days trial$19.991 Year
None

Dating Conversations

No in-app purchases

Questions

Is Inside Then Out free?
Inside Then Out is free to download, with in-app purchases available.
Is Dating Conversations free?
Dating Conversations is free to download, with no in-app purchases.
Do Inside Then Out or Dating Conversations have ads?
Neither Inside Then Out nor Dating Conversations shows ads.
Which is updated more often, Inside Then Out or Dating Conversations?
Inside Then Out ships an update every 5 weeks, and Dating Conversations every 5 days. Most recently, Inside Then Out was updated on October 22, 2026 and Dating Conversations on October 12, 2026.

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