75 Conversation Starters for Old Friends

Old friends are a special kind of comfort. They’ve seen you through embarrassing haircuts, questionable life choices, and probably at least one major heartbreak. But even the strongest bonds can go quiet over time—and that’s okay.

If you’re here, maybe you’re thinking of reaching out to someone who used to be a big part of your life. That’s brave. And honestly, kind of beautiful.

To make things a little easier, I’ve put together a list of thoughtful, funny, and feel-good conversation starters that’ll help you break the silence and reconnect with that person who once knew your favorite snack and your biggest secrets.

Breaking the Ice After Time Apart

1. It’s been way too long—how have you been?
2. I saw something the other day that reminded me of you. How have you been?
3. Do you ever think about how different life looked the last time we talked?
4. What’s one good thing that’s happened to you this past year?
5. Are you still living in the same place or did you move?
6. What’s been your favorite new habit or routine lately?
7. So… what’s one thing I absolutely need to know about your life right now?
8. Ever scroll through old photos and wonder how we survived those days?
9. What’s something new you’ve picked up recently—habit, hobby, mindset?
10. I don’t even know your favorite show anymore—what are you watching these days?
11. I missed our random convos. Want to do a quick catch-up?
12. What’s a small win you’ve had lately?
13. Have you had a moment recently where you just thought, “Wow, I’m really growing up”?
14. Do you still talk to anyone from our old crew?
15. Are you more of a “stay in” or “go out” person these days?

Nostalgia and Shared Memories

1. Do you remember that one time we couldn’t stop laughing… and no one else got the joke?
2. What’s your all-time favorite memory of us together?
3. If you could relive one moment from our past, what would it be?
4. Remember that spot we always used to hang out? Still holds up?
5. What’s one thing we used to love that now feels hilariously outdated?
6. What’s the most random inside joke we had?
7. What’s one memory that always makes you smile—no matter how many times you think of it?
8. Did you ever think we’d drift apart or stay connected all these years?
9. Who do you think changed the most out of all of us?
10. What was the wildest plan we ever came up with?
11. What’s something we did that would make zero sense to people today?
12. What old memory do you wish you had on video?
13. Do you still have anything from those days—notes, photos, weird souvenirs?
14. Ever think about how different things might’ve been if one small moment went differently?
15. What song instantly reminds you of me or that time in our lives?

Life Updates and Catching Up

1. What’s the biggest thing that’s changed in your life lately?
2. How’s work or whatever you’re doing these days?
3. Any major life events I missed?
4. Have you picked up any surprising new habits or routines?
5. What’s a typical day like for you now?
6. Are you still doing that thing you were passionate about back then?
7. What’s one adulting skill you’re weirdly proud of mastering?
8. How’s your family doing these days?
9. Got any pets now? Or are you still allergic to everything cute?
10. Are you still living in the same city, or did you relocate?
11. What’s been the best part of your year so far?
12. What’s your go-to way to unwind after a long day?
13. Any shows, books, or podcasts you’re into lately?
14. Are you in a relationship these days?
15. What’s your idea of fun now vs. back then?

Changes, Growth, and Reflections

1. Looking back, what do you think shaped you the most?
2. What’s one belief or mindset you’ve totally outgrown?
3. What’s something you used to care a lot about, but now… not so much?
4. In what ways do you think you’ve changed the most?
5. What life lesson took you the longest to learn?
6. What part of your younger self do you miss?
7. What’s something you’re glad you unlearned?
8. If you could tell your past self one thing, what would it be?
9. What personal challenge helped you grow the most?
10. How do you define success for yourself now?
11. What’s one piece of advice you always carry with you?
12. What’s something about you that’s stayed solid, even with all the changes?
13. What’s a moment in life that really humbled you?
14. What part of your personal growth surprised you the most?
15. What kind of person are you hoping to become?

Friendship-Focused Questions

1. What’s one thing you’ve always appreciated about our friendship?
2. Did you ever think we’d stay connected this long?
3. What do you think helped us click back then?
4. Do you ever think about how our friendship shaped who we are?
5. I’m curious—what’s your favorite memory of us?
6. Is there something you wish we’d done together but never did?
7. What do you think has kept our friendship strong?
8. How do you usually stay close with people you care about?
9. Has your idea of friendship changed over the years?
10. What kind of friend do you try to be nowadays?
11. What’s something you’ve learned from the friendships that faded?
12. What’s your love language when it comes to friendships?
13. What’s something small that always makes you feel connected to someone?
14. Do you think old friendships are easier or harder to maintain?
15. What would make you feel like we’re really back in each other’s lives?