Sometimes the Hardest Lessons Are the Simplest Ones
I once stood at a charity gala in Buckhead, sipping sparkling water and wearing a dress that cost more than my semester textbooks (a fact my father pointed out with thinly veiled amusement). Somewhere between a tepid conversation about stock portfolios and a whispered debate on monogrammed linens, I realized that despite all the etiquette luncheons and networking mixers, no one had prepared me for the real trenches: dating in the “find yourself before you lose your mind” era of life.
There are things I wish I'd known earlier—things no amount of cotillion lessons or Jane Austen novels prepared me for. So, if you feel like fumbling through your love life is an Olympic sport, here are some hard-won nuggets of wisdom I hope save you a misstep or two.
1. If They Wanted To, They Would
Sure, it’s a cliché. It's also devastatingly, brutally true. I once spent three months “decoding” the text messages of a guy who always seemed a little too busy to meet up. I dissected punctuation like a hormonal Sherlock Holmes. Did the ellipsis mean he's unsure? Or is he giving mysterious, brooding energy? By the time I realized his calendar wasn’t “packed” but rather “selectively unavailable,” I’d wasted an entire summer I could’ve spent flirting poolside with someone who actually liked me as much as I liked them.
The takeaway: Interest doesn’t leave you guessing. If you’re analyzing their texts like you’re prepping for the SAT, you probably already know the answer.
Lesson In Action: Think of effort like a dance partner—it takes two. If they’re not putting on their shoes, it’s time to sit this one out and go find someone ready to groove.
2. Red Flags Don’t Fade, They Deepen
If you meet someone and immediately think, Hmm, that’s kind of a weird thing to say, run that thought through your head like movie credits. Those minor flags? They’re often the opening act for a full-blown circus later on. I once dated someone who made an offhand comment about “disliking brunch culture.” RED FLAG. (Okay, maybe not in isolation, but it led to an entire manifesto against croissant sandwiches and the concept of leisure. Do you know how many bottomless mimosa Saturdays I missed because of that guy?)
The lesson here isn’t to scrutinize someone like a job interview; it’s to trust your gut. Those small quirks you initially brush off will either evolve into lovable uniqueness—or wear you down like wet socks on a long walk.
Lesson In Action: Listen closely and ask yourself: Am I laughing with this person, or am I laughing to distract myself from the sinking realization they might hate Aperol spritzes and joy?
3. Compatibility Isn’t Chemistry
Oh, this is a tricky one. Chemistry can trick you—it sparkles, fizzes, turns every dinner date into an indie romance montage. But you can’t sustain a relationship on butterflies and good lighting. (Trust me, I’ve tried.) Compatibility is about rhythm: How do you spend your time? What values guide you? Do you both agree pineapple on pizza is either genius or a crime against humanity?
I once went out with a person who had more charisma than an awards-show host. We bonded over live jazz and late-night bakery runs. It was a whirlwind… until I realized we agreed on nothing. They wanted a nomadic life hopping from hostel to hostel. I can barely “rough it” in a beach rental without plush linens.
Lesson In Action: When the shimmer of chemistry dims, do you still see them—really see them—as someone you’d share a HomeGoods shopping cart with on Sunday afternoon? If yes, you’re golden.
4. Romanticizing Won’t Rewrite Reality
I don’t know if it’s the aftereffect of binging Austen novels in college or my fascination with Southern Gothic grandiosity, but I’ve been guilty of filling in the blanks of who I desperately wanted someone to be. He wasn’t running late, he was obviously preoccupied planning his brilliant screenplay. He wasn’t uncommunicative, he was mysterious. (Spoiler alert: He was also entirely uninterested.)
Romanticizing is fine for fiction or when you’re daydreaming about a Charleston getaway (which I highly recommend, by the way). But in real life? Don’t fall for a potential that’s stuck in your head. Believe what their actions tell you.
Lesson In Action: When someone shows you who they are, skip the poetic narration and take it at face value.
5. Your Friends Are Your Unpaid Focus Group
Picture this: You’re at dinner, telling your two closest friends about the person you’re dating. One raises an eyebrow, the other casually stabs a baked potato with the subtle aggression of someone deeply unimpressed. Sure, your friends might not get front-row tickets to your love life, but they’re in the balcony seats yelling, “We’ve seen this show before!”
Your friends see patterns you miss when you’re emotionally invested. They’ve also endured the 1:00 AM crying calls when your last relationship turned into a melodrama. Listen to them when they gently (or not-so-gently) suggest you deserve better.
Lesson In Action: Choose friends who love you enough to hand you tissues and a reality check when needed. Bonus points for brunch friends who’ll also swing a breakup playlist your way.
6. Being Alone Isn’t a Punishment, It’s an Upgrade
For years, I considered being single as a holding pattern—a waiting room before the Big Love finally walked in. But here’s what no one tells you: Being alone can be profoundly empowering. I’m talking Sunday mornings spent dancing in your kitchen to old Erykah Badu tracks. Evenings getting lost in a novel while the world outside quiets down.
I’ve fallen in love with my own company, and doing so has made me braver when it comes to love. After all, when you like yourself first, you stop tolerating people who don’t treat you the way you deserve.
Lesson In Action: Light a fancy candle, pour yourself a glass of chilled wine, and toast to your own fabulousness. Being single isn't a timeout—it’s prime time for thriving.
7. Love What You Love Without Apology
Here’s a secret I wish I’d learned sooner: You’re never “too much” or “not enough” for the right person. The ones worth your time will adore you for all your quirks—whether you quote Edith Wharton in casual conversations or have strong opinions about the correct way to boil peanuts.
When I stopped shrinking myself—stopped apologizing for wanting my partner to appreciate my obsession with mid-century Georgian architecture, for instance—I started attracting people who found my passions magnetic. Those who didn’t? They simply weren’t my people, and that’s okay.
Lesson In Action: If your idea of fun is binge-watching period dramas or spending hours antiquing in tiny coastal towns, lean into that—own it unapologetically. Your quirks are gems, not flaws.
That’s the thing about lessons—they often only reveal themselves in hindsight. And while I can’t promise you’ll avoid every misstep, I can promise this: the journey is part of the magic. Whether you’re navigating first dates, awkward text conversations, or long-term commitments, remember that the most important relationship you’ll ever cultivate is the one you have with yourself.
So go forth—flirt shamelessly, love boldly, and don’t let anyone convince you that Nutella-topped waffles at brunch aren’t a valid form of emotional healing. You’re doing great, and I’m rooting for you.
