Cultivating Authentic Friendships
- Brenda Ridgley
- Jul 15
- 5 min read
8 Simple Questions to Deepen Your Connection at any Season of Life
Sister, let's chat about something that's probably been on your mind, especially if you're navigating the beautiful, chaotic journey of midlife: making new friends.
Remember those days when friendships blossomed effortlessly? Playgrounds, school sports teams, dorm rooms – they were all built-in friend factories. But now? It can feel like the world's decided to put up a "No New Friends" sign, and honestly, it can be a bit lonely out there.
We've all felt it, haven't we? That quiet whisper of isolation, even when surrounded by the roles we play and the people we care for. It's like so many of us are craving deeper connections, but sometimes life just gets in the way. Maybe you've noticed your circle shrinking a bit as life shifts, or perhaps new chapters have opened up, leaving you yearning for fresh faces and shared laughter. It's a natural part of our growth, but it doesn't mean we have to settle for less connection.

As a midlife coach dedicated to helping women like you find clarity in your passions and purpose, I truly believe that cultivating a vibrant social circle is deeply tied to our core values, aspirations, and the desires we hold for our lives and the world. The women who truly thrive in building and rebuilding their social connections are the ones who don't just wait for friendship to knock on their door. They initiate, they cultivate, and they open their hearts to the possibilities.
Ready to invite more connection into your Whole YOUniverse? Here are seven simple, heartfelt phrases to break the ice and nurture new friendships, no matter where you are in your journey:
1. "I love your [fill in the blank]! Where did you get it?"
Think of this as a warm, inviting ripple that starts a conversation. It's a genuine compliment, and honestly, who doesn't love hearing something positive about their style or something they're wearing? We often worry about approaching strangers, but more often than not, people are surprisingly open to a friendly chat. Your kind words can instantly make someone feel seen and appreciated, opening the door for a little back-and-forth.
2. "How do you like [fill in the blank]?"
People light up when you ask for their opinion. It's a little secret to connection: when we share our thoughts, it actually sparks joy in our brains! So, next time you're at your favorite coffee shop, ask someone how they're enjoying their latte. At a new gallery, inquire about their thoughts on a particular piece of art. It creates an instant shared experience and shows you value their perspective.
3. "Do you have any recommendations for [fill in the blank]?"
Asking for a recommendation sends a beautiful signal: "I value your input, and I'm genuinely curious!" It's a wonderful way to show appreciation and connect over shared interests. Maybe you're looking for a new book, a podcast, or even a local hiking trail. When they share their recommendation, it gives you a perfect excuse to follow up next time you cross paths. Imagine saying, "Oh my gosh, I checked out that podcast you suggested! I loved the episode on [topic], but I have to know what you thought about [another point]!" Instant connection!
4. "It was great to meet you. I'd love to stay in touch, if you're open to it. How do you like to stay connected?"
One conversation is a fantastic start, but nurturing a friendship means taking that gentle next step. This phrase is gold because it expresses interest without any pressure. Some folks might be ready to exchange numbers right away, while others might prefer a social media connection first. Social media offers a wonderful, low-stakes way to stay connected, giving you little glimpses into each other's lives and easing that transition from acquaintance to friend.
5. "I've enjoyed getting to know you. Let's make plans to hang out more often!"
Friendship, at its heart, is built on consistent connection and a sprinkle of shared vulnerability. Once you've had a few natural, perhaps unplanned interactions, it's time to open up a bit more. Express your genuine appreciation for the connection you've already found, and then take the leap to suggest a deliberate get-together. People are usually quite receptive when there's already a warm foundation in place.
6. "[Something] made me think of you. I've been meaning to reach out. How have you been?"
Sometimes, the most enriching friendships are those we reignite. Life gets busy, and often, old friendships fade not because of incompatibility, but simply because paths diverge for a while. You'd be surprised how much joy people feel when an old friend reaches out unexpectedly. So, if a song, a memory, or even a silly knickknack reminds you of a dear old friend, send that message! A trip down memory lane can be all it takes to rekindle something truly special.
7. "I'm always looking for new friends to [try/do a particular activity]. Would you be interested?"
Think of this as an open invitation! We often hesitate to reach out for fear of rejection, but this approach subtly lets people know you're open to new adventures and new connections. By mentioning specific activities you're excited about—whether it's joining a fantasy book club, trying a goat yoga class, or exploring glass blowing—you're signaling your interests and making it easy for someone to say, "Yes, me too!" When you share exciting, new experiences with someone, it naturally deepens your bond.
8. "I've been working on [my passion/a new project] and I'd love to hear your thoughts."
This one, my dear sister, is about inviting someone into your Whole YOUniverse in a deeper way. When we share what truly lights us up—a passion project, a new hobby we're diving into, or even a challenge we're navigating—it creates a space for genuine connection. It shows vulnerability and trust, and it also gives the other person an opportunity to offer their perspective, expertise, or simply a listening ear. Imagine sharing about a book you're writing, a new skill you're learning, or even a dream you're pursuing. When you open up about what truly fuels your soul, you're not just making a friend; you're building a bond based on shared humanity and mutual support. It allows others to see the vibrant, authentic woman you are, beyond the roles you play, and invites them to connect with your aspirations and desires.
Sister, remember that building new friendships, and nurturing existing ones, is a beautiful journey that enriches your Whole YOUniverse. It's about being intentional, being open, and allowing your true self to shine through. You are worth finding those connections that light you up and truly support your core values and aspirations.
Which of these phrases are you feeling inspired to try first? I'd love to hear about your experiences!
All my love,

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