“You would have saved yourself a lot of tears and three questionable haircuts if only you’d listened to me.” This was my grandmother’s gentle scolding one sunny afternoon in Savannah, her words as soft (and sharp) as her needlepointing. She was right, of course. Almost everything in life—love especially—is a process of trial-and-error, usually heavy on the error. But what if someone gave you the wisdom you needed before the tears, the regret, and the aggressively short bangs? That’s the spirit of this piece. Let the awkward lessons of my twenties and thirties help you dodge a few potholes as you navigate connections, romance, and everything in between.

The One Rule You Can’t Break: Know Thyself First

Here’s the bitter truth wrapped in sweet Southern charm: You can't expect to find a fulfilling connection with someone else before you’re in one with yourself. For years, I was a serial dater—think too many dinner salads and mentally recycling the same “so, what do you do for fun?” conversations. I didn’t realize I was skipping the most important connection of all: the one I owed myself.

What does self-connection look like? It could be morning journals with black coffee, walking alone under the Spanish moss in Forsyth Park, or leaning into hobbies without thinking, “Would this impress someone?” When I joined a pottery class to reclaim the creative messiness of my childhood, it was revolutionary. No one warned me that centering a piece of clay could metaphorically center your expectations in life. So here’s the takeaway:

  • Cultivate rituals that are purely yours—the things that nourish you without requiring an approving audience.
  • Get okay with solitude. No, solitude isn't loneliness in a dramatic white bonnet; it's spaciousness for your thoughts to unfold.
  • Create before you compare. Whether it’s art, fitness goals, or dreams of starting your own bakery, grow something for yourself BEFORE scrolling through the digital highlight reels of others.

By knowing my value beyond what I could offer someone else, I learned how beautiful a relationship could be when it wasn’t built on trying to “fix” or “prove” anything about myself.

Stop Shopping for Red Flags Like You’re on a Scavenger Hunt

Loving someone doesn’t have to feel like a Tim Burton movie—haunting, dark, and all consuming. For far longer than I care to admit, I confused passion with chaos and dismissed every warning sign as “part of the journey.” Exhibit A: There was the guy who thought a gas station rose was romance (it was not), and Exhibit B: The poet who could never decide whether he “believed in relationships” (spoiler alert: he did not). Each time, I missed what my slightly wiser self now sees clear as day. Compatibility means recognizing when someone’s favorite type of drama is creating chaos wherever they go.

How to recognize red flags early without ignoring your instincts:

  • Listen to pattern, not potential. It’s easy to cling to the idea of who someone could be, instead of seeing what they consistently show you about themselves.
  • If their actions talk louder than your excuses, listen. Slow texting you back once is one thing. Repeatedly making you feel unimportant? That’s the story they’re telling you—and it’s not one you deserve to star in.
  • You are not a therapist, a caddy, or the CEO of project management for their personal life. Compassion is beautiful; over-responsibility is not. You’re a partner, not their emotional Atlas.

Looking back, I think I stayed in those relationships longer than I should have because I thought “love is hard.” Spoiler: Sure, love is a mix of elbow grease and patience. But if it makes you feel more anxious than alive? That’s not love—it’s the emotional equivalent of running in quicksand.

Don’t Mistake Chemistry for Compatibility

Here’s the thing about sparks: They’re fireworks, not firewood. Chemistry can be intoxicating during those early dates, but real compatibility is about who shows up when life turns unglamorous. I once dated someone whose idea of romance was spontaneous road trips but who broke into a sweat when faced with budgeting for groceries. Guess what: his knack for picking out artisanal cheeses wasn’t enough to sustain our relationship through the everyday grind.

Instead of dwelling over glittery connections, think about who will hold an umbrella for you when the sky falls apart—or at least who won’t complain when you ask them for one.

What to prioritize when considering compatibility:
- Shared values (even if your hobbies are wildly different). Can you both agree on how to handle money, time, and responsibilities? That’s the kind of glue that outlasts passion.
- Communication style. Are they emotionally open or stuck behind a fortress of polite nodding? Spoiler: Easy conversation now prevents hard miscommunication later.
- Life ambitions that align. If your five-year plan includes adopting a retired greyhound and theirs includes "no plans of any kind," ask if your paths will merge—or if you’re just romantic wanderers clinging to wishful thinking.

People Will Come and Go—Stop Romanticizing “Forever”

Growing up in Savannah with its wrought-iron gates and eternal oak trees, I used to believe in permanence as something sacred. But relationships, I’ve learned, can be both meaningful and temporary. Not every romantic chapter demands a lifelong epilogue.

There was a whimsical summer I spent in Charleston with a poet who taught me the beauty of fleeting connections. I fully knew he and I weren’t destined for happily-ever-after (he was about to move to Alaska, and I very much enjoy not freezing), but the magic of that time carried its own reward. We're conditioned to chase “forever” instead of realizing the beauty of right now.

Questions to ask yourself when letting go of “forever” thinking:
- Was this person in my life for a reason or a season?
- What did I learn about myself from this connection?
- Am I leaving this relationship wiser or more self-aware?

When I stopped equating endings with failure, I found closure—and peace—in realizing that not every bond is “meant to be” forever. And that’s okay. Not every candle was made to burn all night.

Keep Showing Up (For Love and For Yourself)

The hardest lesson? Real love requires risk. Even with all this wisdom tucked away in your back pocket, you still might get your heart broken because vulnerability is never foolproof. But here’s the counterweight: If you never leap, if you never risk—what meaningful life are you building?

Dating, relationships, and connection can feel messy, chaotic, and sometimes downright tiring. But there’s also exhilaration, self-discovery, and—when the right person meets you halfway—a deep sense of belonging that makes every awkward coffee date worth it.

As I keep navigating love in my elegant, humid Savannah corner of the world, here’s my promise: I will keep showing up for love and, just as importantly, for myself. My hope is that you will too.

Go on, take a chance on your own messy, imperfect journey—you’ve earned it. Now, please talk me out of bangs if I mention them again.