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15 Questions to Ask That Will Deepen Your Female Friendships

You feel really close to your female friends — but when’s the last time you had a real heart to heart? In the midst of all the gossip and venting, it can be tough to have a natural conversation about your childhood or plans for the future. If you’re looking to deepen your female friendships, here are 15 questions you can ask to get to know each other even better.

1. What’s your greatest fear?

Maybe it’s snakes; maybe it’s heights; maybe it’s failure; maybe it’s alone. If you want to have a deeper friendship, talking about your greatest fears will take your conversation somewhere it might never have gone before.

2. What’s one thing you’ve always wanted, and what’s stopped you from going after it?

Sometimes, the obstacles are concrete: money, time, health reasons. Other times, they’re more nebulous: fear of failure perceived lack of talent. Whatever the reason, this question will really illuminate what your friend wants and what’s stopping them from getting it — and it just might convince them to try chasing their dreams once again.

3. What are you most insecure about?

Few people like talking about their insecurities, but it can be freeing, and it helps to have a friend who can encourage you and let you know that no one else has really noticed that thing you dislike about yourself. Besides, if you can talk about pelvic floor exercises and Kegel balls with your girlfriends, but not your insecurities, then what kind of friendship is that?

4. What’s your love language?

We mostly think of love languages within a romantic relationship, but it’s important to know what your friend’s love language is in platonic female friendships as well. Whether it’s spending quality time together or receiving thoughtful gifts, knowing the answer to their question will help you all figure out how to show that you love each other.

5. What’s your deepest regret?

All of us have regrets, some big and some small. Whether it’s something, you wish you hadn’t done, or something that you wish you had, discussing your deepest regrets is an opportunity to reflect on how your lives might have gone differently and where you are today.

6. What talent do you wish you had?

Perhaps it’s something practical, like cooking or learning languages easily, or something more fun, like singing or dancing. Whatever the answer is, it will give you more insight into your friend and what they enjoy in their life.

Friends talking
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7. What’s your most embarrassing moment?

This definitely isn’t a question to ask of a casual friend, but sharing embarrassing moments can deepen your friendship and bring you closer. Whether it’s forgetting your bladder leakage pads before an important presentation or spilling soup on yourself during a hot date, your friend will (hopefully) help you see the humor in it.

8. If you had to pick a theme song for your life, what would it be?

Some of these questions can get kind of heavy, depending on how honest you are, so it’s good to have a couple of more lighthearted ones to break up the mood and keep things flowing. This question is fun, but it can also be surprisingly insightful – and forcing you to pick one song really makes you think.

9. Would you ever want to be famous, and why or why not?

Being famous is often a common childhood dream, but priorities change as we age, and many people would never want to become celebrities at all. Your friend’s answer will reveal a lot about who they are and how much attention they want to have on them.

10. When you’re upset, do you prefer to be comforted or to be given space?

This is a critical question in any relationship, especially close female friendships. You might be surprised to discover that rather than being left alone when she’s upset. Your friend would actually prefer to hang out or hop on a call with you to take her mind off it.

11. What’s your favorite thing about yourself?

Balance out the previous question by asking your friend what they love about themselves. Women, in particular, can be uncomfortable with talking themselves up, so push them to give themselves an unqualified compliment about something amazing.

12. If you had to live in a foreign country for a year, where would you go?

Another fun question: this one says a lot about your risk tolerance and how adventurous you are. Jumping the border to Canada is a totally different experience from traveling to Japan, so chat about what country you’d love to spend an entire year in and why you want to go there.

Three friends
Image by Adina Voicu from Pixabay

13. What would your younger self think of where you are in your life right now?

Would your childhood self think that your adult life is totally rad, or would they be disappointed that you didn’t become a Disney Channel star after all? This is a great way to compare where you thought you’d be versus where you are now and to see how your perspective and goals have changed as you’ve gotten older.

14. How are you planning to spend your retirement?

Lots of these questions ask you to reflect on the past. This one prompts you to look forward to the future instead. Another way to think about this question is: If you didn’t have to work and didn’t have many other commitments, what would you spend your time on instead?

15. If you had to pick a superpower, which one would you pick?

What superhero power you pick says a lot about you, from time travel to invisibility to telepathy. Would you and your friend rather be able to fly or to breathe water? The possibilities are endless, and whatever answer you settle on says a lot about you.

Friendships don’t get stronger on their own – you have to work at them. If you’re looking to deepen your female friendships, try asking some of the 15 questions listed here to become closer than ever before.

Featured Image by Adina Voicu from Pixabay