What is the oddest or most random job you had before you landed on this career path?
If you were handed a microphone right now to rant about a trivial topic, what would it be?
What is your specific survival beverage order when the day is going off the rails?
What is the funniest misconception people seem to have about you these days?
If you could leave one specific legacy behind, what would you want it to be?
What is one recurring worry you have about our future that we haven't discussed?
What is a dream you have let go of that still stings a little?
What is a book or podcast you are currently recommending to everyone?
When you are stressed, do you tend to go quiet and focus, or do you need to vent?
Do you get anxious for the first day of the work week and if so, what is your routine to fight them?
If everything ended for you tonight, is there anything you'd seriously regret not saying to someone? Why haven't you said it yet?
If you could magically get the honest answer to absolutely anything about your life or future, what would you ask?
What is the absolute worst memory you have?
When was the last time you cried by yourself?
What was the very first thing you noticed about me, and what was your initial impression?
What do you value most in a friendship?
If you found out you only had a year left to live, would you change anything about your life? Why?
How do you feel about your relationship with your mother?
Make three true "we" statements. For instance, "We are both..."
How would you finish this sentence? "I wish I had someone with whom I could share..."
What is a boundary you struggle to maintain?
If you won a significant amount of money tomorrow, what is the very first boring thing you would buy/pay off?
What was the very first thing you bought with your own money?
When do you feel the most desired by me?
If you could instantly speak any language fluently, which one would you choose and why?
Who was your best friend in your twenties, and what were they like?
Deep Conversation Starter Deck
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What is a seemingly normal activity that you have never actually done?
What is a compliment you received that really stuck with you?
If you died tomorrow, what is the one thing you would regret not saying?
What was your very first leadership experience like?
If you could instantly be an expert in one subject right now, what would you choose?
What are you most looking forward to in the upcoming season of your life?
Deep Questions for Conversations You'll Remember
Get instant access to 250+ timeless prompts in guided sessions and a 30‑day path, so you always have something meaningful to talk about with the people who matter most.
- 250+ curated prompts organized by topic and depth, so you always know what to ask next
- 10 guided "Closer Sessions" for partners, friends, family, and first dates
- 30‑day daily path (one question per day) to build a real‑conversation habit
- Quick‑start shuffle for instant 10‑minute conversations
- Instant digital access from any device
- 7‑day money‑back guarantee
Our guarantee: If you try it within 7 days and don't have at least one better conversation because of it, email us and we'll refund you. No forms, no hoops.
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FAQ
Is this a physical card deck or PDF?
The AskForever Deep Conversation Starter Deck is a digital deck of over 250 prompts with guided sessions and quick-start shuffles you can access from any device. There's no physical deck or PDF. Everything lives in a private online hub so we can keep questions updated and easy to use.
Can I use it on my phone?
Yes! It's designed for your phone. Just open the link from your email and add it to your home screen or bookmark it. You can also use it on a tablet or laptop if you prefer a bigger screen.
Is it only for couples?
No. Many prompts work great for couples, but AskForever is designed for any relationship: partners, friends, family, and even coworkers. Some questions are more intimate and better for romantic contexts; others are perfect for family or friends. You choose who to use each session with.
Will there be new questions?
Yes! We periodically update the Starter Deck with fresh questions, so you'll always have new conversations to explore.
I knew the logistics of her life. I hadn't met her soul in a long time.
We hadn't stopped caring. We'd just stopped asking the right questions.
Read the full story →If you could teleport to any city for dinner tonight, where would we go?
If you could relive one day of your life, not to change it but to feel it again, which day would it be?
If you could make up a new holiday, what would we celebrate?
What is the best piece of advice you've ever received, and did you follow it?
What is a fear or insecurity or worry that has been weighing on you lately?
What is a fear you have conquered that you are proud of?
Ready for your next meaningful conversation?
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