Babies & Bachelorettes: Navigating Friendship in Changing Seasons

Jenna’s baby shower

When my best friend, Jenna, told me she was pregnant back in February, I couldn’t have been more excited for her and her husband, Josh. This was the next chapter they had been dreaming of—something they deeply wanted and had been planning for.

But I’d be lying if I said the excitement wasn’t mixed with a quiet tinge of sadness.

Over the years, I had come to rely on her friendship in so many ways—through joy, heartbreak, and the everyday mess of life. I had grown used to her availability, her presence.

It seemed inevitable that with this major life shift, our friendship would likely change. How could it not?

Around the same time, another good friend, Jen, got engaged. She and her fiancé, Branden, invited me over for Sunday brunch to share the story of their engagement. As we sipped coffee and laughed through the details, Jen asked me to be a bridesmaid. I was honored—and genuinely overjoyed for them.

Funny enough, Jen met Branden the same summer I had become newly single. I was counting on her to be my single sidekick—but clearly, the universe had other plans. (No complaints though—I love how it all turned out.)

While my friends were announcing pregnancies and engagements, I took a spontaneous trip to Toronto—and spent long, quiet hours building this blog, finding my own path and purpose.

Jenna & I: Summer 2024

Mourning the Change

That quiet tinge of sadness I mentioned earlier with the announcement of Jenna’s pregnancy? I kept that to myself, not wanting to dampen even an ounce of her baby bliss—not wanting to steal any joy from this new phase of life she was entering. Ironically, this was exactly the kind of thing I’d normally talk to her about. We’d process it together, scheming to figure out how to navigate the shift. But this time, I felt like I couldn’t. My feelings felt selfish and small compared to the enormity of what she was stepping into.

I tried talking to others about it—about how you maintain closeness with a friend who becomes a new mom—but the most common answer I got was, “You just adjust.” Okay… but how?

Then I ran into an acquaintance who was going through something similar. She’s my age, married, and doesn’t want children—but nearly all of her close friends now have them. She told me her very best friend had a baby, and things shifted so much that she had to mourn the friendship. Not because they stopped caring for each other, but because they rarely saw each other anymore, and it would never be quite the same again.

I had never thought to call what I was feeling “mourning.” It sounded so dramatic. But the moment she said it, it struck me as truth. I wasn’t wishing I was in the same stage of life as Jenna. I was simply watching our paths diverge—and it made me sad. I knew there was a version of our friendship that would remain in the past, slowly shedding so it could evolve into something new.

Jen & I at her bachelorette weekend in Fergus Falls

When Your Friends’ Milestones Don’t Match Yours

Jen and I became friends right around the time I ended a long-term relationship. Back then, she was single but dating, and we’d often swap stories about relationships and the wild world of modern dating. We connected over our shared love of interiors and decorating, self-development, and travel—she’s all things bright, colorful, and full of energy.

So when I found myself newly single, I thought, Well, at least I have a good, fun, single friend!

That didn’t last long. Two years later, she’s engaged… and I’m still single.

I don’t know if it’s just me, but it seems like my parents’ generation—and those before them—tended to move through milestones in sync. Friends got married and had kids around the same time, growing together step for step. You sought marriage or parenting advice from peers who were in the thick of it too, which I’m sure created a bond of deep understanding.

Today, though, that’s not necessarily the case. Our timelines zigzag. Some friends marry young, others much later, and some not at all. Babies arrive for some in their twenties, others in their forties—and for some, never. The paths are far less predictable now, and nothing can be assumed.

Jenna, Me, & Jen: Summer 2023

How Do You Stay Connected When Everything’s Changing?

I still find small ways to pull Jenna into my knack for adventure. Like when I insisted we check out the allegedly haunted Palmer House Hotel while we visited her hometown this spring. And when we were mapping out our summer plans, she didn’t even blink when I suggested going to a Killers concert—at five months pregnant. (We ended up not going, but her excitement and willingness said it all.) And when it’s just the two of us, I sip a mocktail alongside her while she schools me on the hundred different kinds of baby strollers, or I help her pick out furniture and décor for her nursery. We’ve since had honest conversations about the very changes I was once hesitant to bring up, and talking about it made the shift feel less like “mourning” and more like choosing a new way forward.

With Jen—even in the middle of wedding planning and a calendar packed with commitments, we still carve out time to catch up. I’m happy to hear every detail—from the guest list to the center pieces—and we still get to connect over the fun, creative parts we’ve always loved: color palettes, decor ideas, and finding beauty in the details. Our conversations have shifted from dating apps to wedding hors d’oeuvres—and I’m honored to have a seat at the table for it all. There’s something truly special about witnessing a friend’s growth and getting to share in their life—whether it’s the quiet details or the biggest celebrations.

We find a way to meet in the middle. Because friendship isn’t about having everything in common; it’s about showing up, adapting, and making space for each other’s journeys, regardless of how different they may be. No matter your stage in life, you still need that steady, unwavering support.

I’m not saying it’s always easy, but I suspect that’s what it takes for a friendship to grow—and last.

Spontaneous trip to Toronto in February

Making Peace With Your Own Timeline

There was a time when I felt like I had to find a partner. Somewhere along the way, I’d absorbed the idea that partnership was the next box I was supposed to check. The search became exhausting and, if I’m honest, unfulfilling. It felt like chasing something I had no real control over.

So what was I doing with my empty evenings? Mostly Netflix, if I’m being honest. I had so much extra time on my hands simply by being single—and I was wasting it on the wrong chase.

So I made a decision: I would stop trying to fit someone else’s timeline. Instead, I’d fill my days with work, creativity, friendships, family, and travel. I’d pour my energy into pursuits and people that gave me life—not drained it.

And now? That’s exactly what my life looks like. Even as Jenna steps into motherhood and Jen plans her wedding, I’m learning to stay rooted in my own season. I’ve successfully built a life that feels like my own. If you’ve been following along with my blogs, you’ve probably noticed this thread running through many of them: the last two years have been a season of enormous change, of slowly reshaping my life into one that actually fits. I have learned that I don’t need to measure my life against anyone else’s—I simply need to live it fully and intentionally, staying true to my own path.

Olivia & I at Feast of Nations gala

Shared Stages, Different Ages

In line with my decision to pour my energy into pursuits and people that give me life, one of those people is Olivia—a friendship that emerged this past spring. Even though we live on the same apartment floor, we actually met through mutual acquaintances first. We quickly realized we shared a lot in common, especially when it came to our dating pasts. She’s creative, sharp-witted, and smart.

Even though she’s seven years younger than I, we’re in similar life stages: focused on work, growth, investing in our friendships, seeking out adventure whenever we can, and yes—talking about boys. 😉

Together, we do fun, spontaneous things: art galleries and galas, impromptu swimming days, dive bar patio drinks, concerts. I pick up new Gen Z phrases and pretend not to feel old. Sometimes we stay out too late, then debrief the night over brunch and Bloody Marys, laughing our way through the morning. It feels like we’re both a little lost in the singleness world together, and it’s nice to have company.

Connection isn’t always about age or timelines—it’s about finding someone who gets you.

Hozier concert with Olivia and Sarah

How Do I navigate My Friends’ Major Life Changes?

I show up—just as they showed up for me when I started my own business, started this blog, started over. Sometimes that means my married friend listening supportively to my dating-in-the-wild adventures; other times, it’s my single friend right there in the trenches with me, fully commiserating.

This past month, I had back-to-back weekends that took me from Jenna’s baby shower to Jen’s bachelorette party to a Hozier concert with Olivia and friends. One night it’s live music and staying up way too late; another, it’s sitting in a flower-filled room at a baby shower, quietly watching a new chapter unfold.

I’ve learned so much from all of them. And yes, I still have to process how these changes make me feel—what they mean for me and for our friendships. But showing up, even while grappling with it all, feels like the best place to start. Change isn’t inherently good or bad—it’s just different. Accepting change, along with all the mourning, joy, confusion, fear, and excitement that comes with it, seems like the best remedy. At times, it may feel like you are worlds apart from your friends, and there is a quiet sadness in that. But I have found that knowing you’re on the right path, and your friends are on theirs, brings the truest peace of mind.