I was once asked, by of my Honey Bees to write a story about the type of questions I would like to ask my close friends. This gets somewhat complicated because if they are already close friends, shouldn’t we know what makes them tick? These women are ‘the cream in our coffee.’ They add delicious flavor to our lives. We share thoughts, we ask questions and we give one another advice, therefore what additional questions do we have left to ask? Plenty darlings, plenty…

Upon reflection, close friendships are not meant to match the intimacy of a husband and wife. Even in the closest relationships, it’s important to respect personal boundaries and recognize the value of alone time for individual well-being and maintaining intimacy.

Close Friendships, Have You Asked 20 Questions to Ask?

I think of close relationships, it’s hard not to first think of my ultimate concierge. Our relationship is near perfect because we allow ourselves to be an open book with no secrets from one another. Upon reflection, close friendships are not meant to match the intimacy of a husband and wife. We can peel back and share layers of deep thoughts with our closest friends, but there are private situations and thoughts every woman keeps close to her chest.

When a close friend helps you swim to a safety net, you know she cares. When a close friend showers you with joy for an opportune circumstance, you know she is genuine, When a close friend defends you in front of others, you understand her loyalty. When you are within the company of close friends and you do not notice the time slipping away, you know you have simpatico, shared attributes and interests. What else do you need to know?

My Honey Bee came up with an interesting idea for a story. It would be enlightening to hear my closest friends’ answers to my questions. Likewise, it would be equally challenging for me to come up with my own thought-provoking questions. Asking about how someone has felt during significant moments or how she feels about certain life changes can lead to a deeper understanding of her experiences and emotions. Questions like, “What is the most important lesson or an important lesson you have learned from past relationships or experiences?” can be a powerful way to foster connection and personal growth.

We know women over 50  need one another and want strong friendships. No woman should be an island unto herself. No woman should stand alone. The deeper we understand our closest girlfriends’ psyches and vice versa, the stronger our bond becomes.

A Surprising Realization

Although we think we know our closest friends, I came to the surprising realization that there is plenty we don’t actually know about each other. We spend our time talking about social gossip, family drama, parents, parent, shopping, travel, what we are going to do with the rest of our lives, retirement, diets, politics, health issues, the latest fashion and beauty products, and life transitions, which are also important topics that often come up in conversations among women over 50.

Sometimes, the most interesting conversations come from asking about how our experiences have shaped our view of the world. Asking about the most strange or unexpected experiences can also reveal new sides of our friends.

However, rarely do we ask each other truly personal questions. Those are saved for the shrinks or as my ultimate concierge calls these professionals, stretches. While most women thirst to reveal their feelings, they stop short because they don’t want others, even their closest friends, to see their vulnerabilities.

Let’s Play A Game of 20 Questions

Most women thirst to talk. I know this because I have put together two groups of ten women that met monthly. I’d love it if you joined one of my private Facebook groups (I have three groups that serve women going through different transitions). Why? We women over 50 want to talk; we want to share. We want to belong. Most importantly, we want to grow and we don’t want to feel lonely.

Women over 50: Celebrate Visibility

Sisters in Widowhood: Life Transition

Estranged Mothers and Grandmothers: Millions Strong

Discussions of deep issues within groups work. I think deep conversations between very close friends can also work. In group settings, topics like dating, start dating, and memorable dates often come up and can spark interesting discussions. It helps to play the 20 Questions game to explore anything you’re experiencing, including questions about spending habits or financial decisions, which can be valuable in understanding each other. Friends also support each other through breaking points or breakups, offering comfort and advice, and acting as a support system for one another. Group conversations can help turn a stranger into a close friend. I think before long, you will be knee deep in contemplative conversation, feeling closer than ever and building even stronger relationships.

Funny Moments and Lighthearted Conversations

Laughter truly is the best medicine, especially when it comes to nurturing close relationships. While deep, serious questions can help us understand each other’s core values and life experience, it’s often the funny moments and lighthearted conversations that bring us closer and make our time together unforgettable. Whether you’re reminiscing about your first date, sharing stories from a past relationship, or simply chatting about your favorite season, these playful exchanges can break the ice and foster connection in ways that serious questions sometimes can’t.

If you’re looking for questions to ask your close friend that will spark laughter, consider diving into the lighter side of life. These types of icebreaker questions are perfect for starting fun and engaging conversations. Ask about the weirdest thing they’ve ever eaten, the most spontaneous thing they’ve done in their free time, or the funniest story from their childhood. You might be surprised by the stories that come out—like the time someone went on their worst date ever, or the most embarrassing moment they had with family members. These conversations not only bring joy, but also help you understand your friend’s sense of humor and what makes them feel special.

Don’t be afraid to sprinkle in some small talk about pop culture, like the last movie you watched or your favorite thing to binge on a lazy Sunday. Are you a morning person or a night owl? Do you have a bucket list of fun things you want to do, or a favorite way to spend your spare time? These lighthearted questions can reveal so much about your friend’s personality and daily routines, and they’re a wonderful way to spend time together.

Of course, it’s also fun to ask about the best compliment your friend has ever received, what makes them feel sexy, or their go-to love language. Sometimes, the silliest questions—like what Jeopardy category they’d dominate, or the most spontaneous thing they’ve ever done—lead to the most memorable conversations. And who knows? You might even discover a new favorite thing to do together!

Remember, relationships thrive on a balance of serious and funny conversations. While it’s important to talk about your biggest fear or the lessons you’ve learned from a relationship end, it’s equally vital to laugh, be silly, and enjoy each other’s company. So next time you’re with your best friends, don’t hesitate to ask those funny questions, share your stories, and let the laughter flow. After all, the best gift you can give each other is the joy of feeling understood, appreciated, and truly connected.

Creating a Bucket List Together

There’s something magical about sitting down with a close friend or partner and dreaming up a bucket list together. Whether you’re reminiscing about your childhood, sharing stories about family members, or simply looking for a fun way to spend time, creating a bucket list is a wonderful way to foster connection and deepen your understanding of each other’s dreams and desires.

This activity isn’t just for couples planning a dream wedding or those on a first date—it’s for anyone who wants to add a little adventure and meaning to their relationships. When you start dating someone new, or even if you’ve been best friends for decades, asking questions like, “What’s the most spontaneous thing you’ve ever done?” or “What’s your favorite season and why?” can open up new avenues of conversation and help you understand what makes each other feel special.

As you talk and brainstorm, don’t be afraid to dream big. Maybe your dream job is still on your mind, or perhaps you’ve always wanted to write love letters, learn a new language, or volunteer for a non-profit together. The beauty of a shared bucket list is that it can include everything from the most spontaneous thing you can imagine to the simple joys of life, like planning a cozy movie night or taking a cooking class.

Remember to consider your core values and financial goals as you create your list. It’s important to steer clear of activities that might cause stress or strain your relationship. Instead, focus on experiences that bring you joy, laughter, and a sense of togetherness. Some ideas to get you started: plan a surprise getaway, create a scrapbook of your favorite memories, or set a goal to try something new every season.

The most important lesson in creating a bucket list together is learning how to communicate openly, support each other’s dreams, and celebrate the journey—no matter where it takes you. So, gather your best friends, your partner, or even your family, and start talking about the adventures you want to share. You’ll not only discover new things about each other, but you’ll also create memories that last a lifetime. And who knows? You might just find that the real joy is in the dreaming, the planning, and the laughter along the way.

In All Seriousness, Let’s Play 20 Questions

1. What scares you?
2. When you are upset, do you want to talk or do you want your space?
3. How do you like to spend your alone time?
4. What are you most insecure about?
5. What is your ideal house or living arrangement?
6. What qualities do you value most in a partner?
7. How do you feel about spending and managing finances?
8. How have your parents influenced your life?
9. What is the most important lesson you learned from being a parent or from your parents?
10. How has your view of the world changed as you’ve gotten older?
11. Have you ever experienced a breaking point in a relationship? How did you handle it?
12. What was your experience like when you first started dating?
13. What is your favorite memory from a date or dates you’ve been on?
14. What is the most strange or unexpected thing you’ve learned about yourself?
15. Have you ever felt like a stranger in your own life or among friends?
16. When was a time you truly felt seen or understood by someone?
17. How do your feelings about aging or relationships differ from how you felt in your 20s or 30s?
18. What is the most important lesson you’ve learned from a past relationship?
19. What important lesson would you want to share with your friends?
20. Do you believe gratitude gives you latitude?

There is my list, darlings. Choose from it as you like. This exercise will open the door to a deeper understanding among all of us women over 50, which is positive psychology at its best.

If any of you are open to sharing, I would appreciate your stories regarding any of the questions that pique your interest. Darlings, how can we better learn from each other so we can all help each other grow?

 

If you are not a member of one of my Facebook groups, I would love for you to join me. Come find your supportive community of like-minded women! Join these private Facebook groups:

 Women over 50: Celebrate Visibility

Sisters in Widowhood: Life Transition

 Estranged Mothers and Grandmothers: Millions Strong