There’s a house on Savannah’s East Jones Street that always stops me in my tracks. Its wrought-iron balcony curls like a question mark against the soft blue sky, and the shutters—weathered to perfection—are painted a shade of green that feels plucked from the pages of an old memory. It’s here that I met Caroline Ward, the friend who, without hesitation or ceremony, changed my life.
If this sounds overly poetic, I can assure you that at least some of my awe is due to the fact that Caroline arrived in my life with the subtlety of one of those Hollywood makeover montages. Except, instead of granting me access to a new wardrobe or a magical chance to land the leading guy, she gave me something I hadn’t realized I was missing—a way to truly be myself.
The Day Our Stars Aligned
Caroline wasn’t from Savannah. She didn’t know the difference between dogwoods and magnolias at first glance, a fact which, to my lifelong-Southern self, was both baffling and oddly endearing. She hailed from somewhere outside Philadelphia, her vowels clipped and speech quickened. But Savannah had called her southward, and she responded in kind.
We met during my third year of running historic house tours, an eerily warm Tuesday in April. Most of our visitors were retirees clutching guidebooks, but Caroline stood out. She was younger, mid-twenties, with a canvas bag slung over her shoulder and white sneakers I later learned would never stay white. She asked all the wrong questions (Caroline always asks the wrong questions), but they were refreshingly curious—Why aren’t there more paintings of people smiling? How many people do you think fell down these stairs before they realized the banister was such a bad idea?
When the crowd dispersed, she waited by the doorway, leaning her weight into one hip as though the building itself might invite her to stay. “Do you want to come to lunch?” Her boldness caught me off guard. I hesitated, weighing the prospect of skipping my usual solo salad for an afternoon with this half-stranger. But something about her disarming ease prompted me to say yes.
The Friend Who Made Me Question Everything
You know those moments when someone hands you a treasure you didn’t even know you were missing? That was Caroline, summed up in one fanciful burrito bowl we shared on Broughton Street. In her company, I felt a little braver, a little lighter. My world, which had up until that point been defined by preservation and carefully folded corners, seemed less daunting.
Caroline was the first person to ever encourage me to challenge my “supposed to.” Supposed to stay in Savannah. Supposed to marry young. Supposed to say yes more often than no. She disrupted everything so gently, like the way humidity lingers in the air after sunset.
It wasn’t always easy. Friends that change your life have a way of putting a mirror up to your choices, and not everything reflected back feels flattering. She could do this with humor, too, which was all the more infuriating. One evening, after I made an offhand gripe about my work struggles, she tilted her head and asked, “You love the houses, but do you maybe hate the schedule?” All I could do was laugh, shocked that she’d cut to the truth faster than I ever dared admit it.
How She Taught Me to Unfurl
Every piece of my adult life now feels calibrated by a small moment with Caroline. She taught me how to host a dinner party—effortlessly, with mismatched plates and wine served in jelly jars. “They’ll remember the fun, not the forks,” she’d say after a spill.
She introduced me to offbeat movies and writers I thought I didn’t have time for. She showed me how to ask questions that mattered—not, “What’s your degree in?” but “What’s the weirdest job you’ve ever worked?” And she coaxed me into my first (and last) tandem bike ride, which predictably ended in mess and laughter near Forsyth Park.
Above all, Caroline’s greatest gift to me was what I’ve come to call her “yes-and” approach to life—borrowed from improv, no doubt intentional on her end. Whenever I’d find myself paralyzed by indecision, she’d nudge me toward a choice, as if to say, “Pick something, see what happens, and build from there.” It’s how I left my tour job to pursue writing full-time—something I’d always wanted but never thought practical. “Practical!” Caroline had scoffed when I’d told her my fears over coffee one sky-split morning. “Who made up that nonsense?” she teased.
The Ways I Pay It Forward
Caroline doesn’t live in Savannah anymore. Her path took her westward, toward Austin, a city as unabashedly quirky and bold as she is. But her lessons live on, tucked into my life as inseparably as Spanish moss is woven into my city’s oak trees.
Now, when I see friends weighed down by self-imposed expectations, I think: What would Caroline say? I encourage them to pause, breathe, and aim for joy over perfection—or at least laugh along the way.
I set tables a little looser whenever I host, part of me wishing Caroline could see the guests clinking jelly jars here in Savannah as the sun sinks into the river. I linger in bookstores and act on whims, like buying that paisley dress once marked too bold for me. I even let myself try and fail (recent bonsai attempt, case in point).
When Someone Else Sees the Real You
Caroline taught me something vital: If you’re lucky, friendships can become a kind of mirror, the kind that reshapes how you see yourself and your life. It’s not just that she cheered me on—though she did, wildly, often before I’d even finished describing my hopes. It’s that she saw the parts of me I’d tucked away, the messy adventurer buried under a decade of predictability. She held those pieces to the light and simply said, “Go.”
To anyone reading this: maybe your “Caroline” is already in your orbit, or maybe they’re still on their way, sneakers at the ready. Either way, I can promise you this—a friend like that will change everything. And when they do, you’ll wonder how you ever lived without them. So lean in. Say yes. And maybe, somewhere along the way, you’ll start to see the best version of yourself, reflected in their eyes.
