What was your first impression of me? What surprised you after getting to know me?
What do you think comes easily to me that's hard for others?
What do you think I'm sensitive to?
Which one of your other friends do you think I'd be the most compatable with? Explain.
What's one small detail you remember about the first time we met?
What qualities do you think I need most in a long term partner? What do I tend to go for?
What made you gravitate towards me as a friend?
Describe my ideal roommate. Who could I never live with?
What do I have a low tolerance for in people?
What assumptions do you think strangers make about me based off of my social media?
What about me is most intimidating, if anything?
What (or who) do you think I spend most of my time thinking about these days?
How many unread texts do you think I have right now?
On a scale of 1-10, how sexually adventurous do I seem?
What do you think I strongly dislike that most people obsess over?
When do you think I wake up on an average day? Explain.
How many people do you think I've slept with?
Who do you think I'm closest to (besides you)?
What am I most likely to walk out on a date because of?
What's something I'll never say no to?
What's the first thing you noticed about me?
What's something I could do for hours on end without getting bored?
What's something I could give an hour-long presentation on right now?
From your perspective, what would this chapter of my life be called?
What assumption did you make about me that was way off?
Who's the more hydrated friend?
Who do you think was the last person I stalked on social media? What was I looking for?
What about me would people least expect?
What outfit am I most likely to wear on a first date? Get specific?
When do you think I'm most 'in my element'? What do you think I'm doing? Who am I with?
If I had a movie poster on my wall, which would it be?
What do you think my circle of friends has in common?
What about my style is undenyably me?
Who in my life do you think brings out the best in me?
Describe my ideal first date from start to finish.
What have you been extra hard on yourself for lately?
What are you tired of complaining about?
What are you trying not to think about?
When do you feel most like yourself? Who are you with? What are you doing?
What do you wish you got more credit for?
Do any of your friends no longer feel like friends?
What's an exciting change you've been seeing in yourself, big or small?
What have you learned to accept about yourself with time?
What do you need to vent about right now?
Who's a friend you've lost touch with that you think about to this day?
Who was your first best friend and one thing about them?
How many times has your 'best friend' changed through the years?
Does our friendship have a defining moment? What was it?
What are you proudest of yourself for? You have permission to brag.
If you could relive an iconic day in our friendship, what would it be?
What made you smile today?
Is there a pattern you've noticed in my love life?
Who in your life leaves you feeling drained? What boundary could you set with them?
What (or who) have you been overthinking?
What conversation are you avoiding?
What could you benefit from letting go of? Why are you still holding on?
What do you want to make more time for? What's getting in the way of that?
Have you ever had a friendship breakup before? What did it teach you?
What are you procrastinating right now? Why does it feel so hard?
What text would you send right now if there weren't any consequences?
What's one small thing someone's done for you recently that made you feel loved in a big way?
When was the time you were a bad friend? What could you have done differently?
What part of your job doesn't feel like work?
What are you still processing?
What's the most loving thing you've done for yourself recently?
What's the hardest part about making new friends for you?
Rate your happiness level at your current job on a scale of 1-10. What would make it 1 point higher?
What have I introduced you to that you now love?
What was your first impression of my most recent partner? What do you think now?
Were you comfortable having friends over growing up? Explain.
What's something you can always rely on me for?
How have you seen me change over time? What hasn't changet at all?
What makes our friendship work?
What was hardest for you to open up to me about?
When do you feel closest to me? What are we doing?
When was the last time you had a big win? How can we celebrate?
What's a habit of mine that you're inspired by?
Have I changed your mind about anything?
What do I need brutally honest advice about?
What growth have you seen in me recently that's been exciting to watch?
What do you think I need to hear right now?
What are you proudest of us for getting through together?
What's something I don't give myself enough credit for?
What's the best way I can show up for you when you're going through it?
What's one thing you cherish about our friendship?
What do you think I'm growing out of? What do you think I'm growing into?
What's something that reminds you of me?
Is there any way our friendship has raised your standards for all the rest?
What song(s) make you think of me?
What's a philosophy of mine that you'd like to adopt?
How has our friendship changed you for the better?
What's something we used to take for granted? What's something we could be taking for granted now?
How have I helped you without realizing it?
When you're upset, what do you need most?
In what ways do our differences compliment each other?
What's something I should stop apologizing for?