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54 Questions to Ask Your Long-Distance Friend


Distance makes the heart grow fonder, but also makes having spur of the moment heart-to-hearts with your best friends kind of challenging. One easy way to get (or keep) a conversation going is through asking questions. Whether you’re in need of a quick laugh, something more serious or an easy prompt to reconnect, there’s a question on this list for you.

It's time to rekindle friendships intentionally. Start with this list.

Questions to Ask When You Need to Reconnect

Let’s be real: life goes really fast sometimes. And you might just lose touch with important people in your life.

That’s okay.

When you’re ready to restart the conversation, use these easy, no pressure questions:

  • Long time, no talk! What’s the most exciting thing that happened to you recently?
  • I’ve been really thinking about (fun memory together). Remember that day?
  • I miss you! Want to have a virtual coffee date?
  • I’ve missed so much! Want to schedule a quick chat to catch up?
  • What’s up with you? It’s been a minute since we talked!
  • How are you doing?
  • How did (something your friend did or was excited about last time you talked) go?
  • I miss you! Can you talk right now?
  • What’s the weather near you today?
  • How are (pet, family member, etc.) doing?

Serious Questions to Ask Far Away Friends

Sometimes, things need to get serious. Hey, life isn’t all light and fluffy all the time either!

Add these questions to your next conversation to reach a deeper level of friendship.

  • Are you doing okay?
  • I noticed you seem a little (mad, sad, blue, down, frustrated) lately. Is everything okay?
  • I wanted to make sure that you are doing well right now. I know things are tough.
  • How can I support you right now?
  • How do you see me?
  • Do you feel like our friendship is balanced and equitable?
  • Do you need help?
  • I need help. Can we schedule a regular accountability check-in time?
  • If I needed help with (kids, health, etc.), can I turn to you?
  • Can I add you as my child’s guardian in my will?
  • Can I add you as an emergency contact, even though you live far away right now?
  • How do you feel about (politics, touchy social issue)? No judgement!
  • I’d like to be able to vent to you. Can I do that?
  • Am I overwhelming you with my needs? Please be honest!

Silly Questions to Get to Know Your Friend Better

Life can be serious, but also, sometimes you just need to laugh a little. There’s no better person to share a laugh with than a friend!

Pull out these questions when you need to giggle (and maybe learn a little more about your buddy).

  • Have you ever had a celebrity encounter?
  • Can you connect yourself to Kevin Bacon in six steps or less?
  • What’s your favorite food?
  • What food would you never eat? Not even for a million dollars?
  • Cake or pie?
  • Coffee or tea?
  • Water or something else?
  • Wine, beer or a mixed drink?
  • Chocolate or vanilla?
  • Favorite childhood outfit? What was it and why?
  • Do you have any toys that you’re hanging on to from when you were little?
  • You have a whole day to yourself and unlimited funds. What are you doing?
  • What is the #1 place on your travel bucket list right now? Why?
  • Who was your first crush? How old were you?
  • Best subject in school?
  • Do you have a secret talent? Can you show me on our next Zoom chat?
  • What’s your favorite board game? Why?
  • Do you have a house feature pet peeve? Like one thing that is a hard pass in a house that would prevent you from renting or buying?
  • Tell me one thing you must have in your dream forever home!
  • Find the weirdest thing in your purse/backpack and give me clues so I can guess!

What to Ask When You Want to Deepen Your Bond

When you’re friends for life, but you’re not co-located, increasing your bond can be a challenge. Luckily, these questions and prompts can help you do just that!

  • Tell me you’re my friend without telling me you’re my friend.
  • What’s your favorite memory of our friendship?
  • Let’s make a friendship goal for this year. What do you want to commit to doing together?
  • Want to do a subscription mystery kit together?
  • I found this cool (virtual event you can share). Want to do it with me?
  • What’s the very first thing we’re going to do when I visit you?
  • When you visit me, what’s on your bucket list?
  • Can we pencil in a real life visit or vacation?
  • What’s your ideal best buddies vacation spot?
  • Let’s plan on having a regular video chat. What time and day works best for you?

Building friendships over long distance takes work and effort. But with a few pointed questions, you and your bestie will be on track for hours-long FaceTimes, phone calls or text messages!

Keep reading…

Meg Flanagan is a teacher, blogger and military spouse. She owns Meg Flanagan Education Solutions, an education advocacy service dedicated to serving families on the K-12 journey. You can find Meg on Facebook. Meg is also available as a freelance writer and personal education advocate!


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