The best questions to ask your best friend invite a story instead of a one-word answer. You probably know their coffee order and their favorite movie already. You may not know what they are quietly proud of this year, what they miss, or what they hope your friendship looks like later on. Here are questions sorted by the past, the present and the future, plus a few ways to ask them that keep things relaxed.
Questions about the past you share
A long friendship comes with a stack of shared stories, and each of you tends to remember different pieces. That makes the past an easy place to start. There is no wrong answer, nobody has to reveal anything new, and the memories are already there. Pick one question and ask what they remember that you might have forgotten.
- What is a moment from our friendship you think about more than I would guess?
- When did you first feel like we were actually close?
- Which version of us from a few years ago do you miss a little?
Questions about who they are right now
Best friends can slip into trading updates about work, family and weekend plans. These questions ask about the person instead of the schedule. They work well on a walk or a long drive, when you are side by side and a pause does not feel awkward. Give each answer room before you move on, and ask one follow-up about the part that interests you most.
- What has surprised you most about this year?
- What are you quietly proud of that you have not told many people?
- What do you want more of in your life right now, and what do you want less of?
Questions about the future and your friendship
The most personal questions are about the two of you. Save them for later in the conversation, once you are both settled in, and keep them curious rather than critical. They are not a test of whether the friendship is working. They are a chance to hear what your friend values and what they would like to do together.
- What is one plan you would love for us to actually make happen?
- What do you hope we still do together when we are much older?
How to ask without it feeling like an interview
Go first. Answer your own question before you ask it, so it feels like a trade rather than a quiz. Ask one or two, then let the talk drift wherever it goes. Either of you can pass on any question without explaining why, and a short answer is still an answer.
You do not need a big night out for a conversation to count. A University of Kansas study had over 900 participants from five university campuses. KU News reported that talking with a friend just once during the day, to catch up, joke around or say you are thinking of them, can increase happiness and lower stress by day's end. It did not matter which kind of quality conversation people had. Intentionally reaching out was what mattered most.
Common questions about asking your best friend deeper questions
What if my best friend does not like deep questions?
Keep them light and try one on a day that already feels easy. Some people open up more while doing something else, like cooking or walking. If a question gets a shrug, take that as a no for now and change the subject.
Can you ask these questions over text?
One question at a time works well in a chat, especially when you live far apart. The KU study also found high-quality, face-to-face communication was more closely associated with well-being than electronic or social media contact, so save a favorite question for the next time you are together.
How many questions should you ask at once?
Fewer than you think. Two or three with real follow-ups can fill an evening. For a ready supply, keep a short list on your phone, use a card deck, or open a question app such as Paloma.