Hi Reader,

I was a late bloomer when it came to friendship and having a social life.

Awkward in high school, quiet in college, and devoted to academics and athletics. I was a “great student,” but socially, you’d often find me studying, sleeping, or avoiding the big crowds.

It took me a long time to find rooms where I felt like I belonged. Honestly, I learned things in my twenties and thirties that I wish folks had explained to me much earlier in life. There isn't a good manual for what friendship is supposed to look like!

The thing is, I still feel pretty awkward today, almost every day of my life. But I’ve realized something important along the way:

Friendship and connection are a dance of repeated attempts.

Someone has to smile first, ask a question, send the text. Every time we put ourselves out there, we risk the possibility of a slightly awkward moment. What I’ve gotten better at isn’t that I'm not longer awkward. (Oh, I'm still quite a silly weirdo through to this day!)

I’ve gotten better at being willing to go first.

Author and friendship researcher Dr. Marisa Franco taught me one of the simplest ways to spark a small connection attempt: pair an observation with a question.

Notice something small about the person in front of you or the room you’re in — the music, their shirt, the food, the coffee, the event itself — and get curious about it.

The formula: observation + question

• This is a great event. How did you hear about it?
• Oooh, is that a cortado? I’ve never had one. Is it good?
• I love your shirt! Where did you get it?
• Those tacos look spectacular. Do you recommend the food around here?
• I love the music they’re playing in here. Do you work here often?

That’s it.

Notice something. Ask something. Be willing to go first.

These bids are small, and most of them close quickly. But some of them spin off into longer conversations, and that's how we end up finding someone else out there with a similar vibe to us. The more attempts we make, the more likely the payout.

We don't have to be effortlessly charming or perfect. We just have to make a lot of attempts.

Be brave and be kind.

— Sarah

Read this to understand why we're so lonely:"One person cannot be everything and everyone for another person. Our partner cannot be our therapist and our confidante and our bowling pal and our reading group and our cooking group. It’s impossible to be all of this to each other. A marriage is not enough. A friend is not enough. We need more people."

Watch this for a great starter question to a new connection: Two questions you can ask that are better than "How are you?" and GREAT for networking events and getting to know people.

Say this when you want to build casual local community: "Come over to my messy house and let's do a puzzle or a game together."

Finding your right people.

Next week, we’re gathering a group of women to talk about the ways in which we manage, grow, and even let go of friendships as we go through midlife. Join us (for only $20!) at a wonderful salon to connect, to really talk, and to share what’s working. Be seen and be heard with us. September 2. Register here.

Every year, I run The Council, a circle where we go deep and really get to know each other. People have made life-long friendships because of it, and the community has grown over the years. We’re now open for applications for the Fall 2026 cohort. Apply to join The Wise Women’s Council today. Early bird applications are open through September 8th.​

​Writing Club meets every Monday. We sit on zoom and we WRITE. Folks are writing their weekly LinkedIn posts, they’re editing chapters, they’re making messy mind-maps. It’s where I write this weekly email! Apply to join us today. Our next group starts September 14th.

This week's idea:

Awkward, weird, silly? Me too. You're totally lovable as you are right now. Be awkward and be brave. Go first. Ask someone about their day. Text a friend. Tell someone you love them. We all need more connection.

— Sarah