The Struggle Nobody Saw Coming

It started with an innocent-enough comment from my mom one Sunday afternoon as we sat in her Miami kitchen. She was dicing onions for picadillo, and I was nursing a café con leche, mostly to avoid getting roped into kitchen duty myself. Out of nowhere, she looked up and said, "Mijo, ¿cuándo te vas a calmar?" Roughly translated: “When are you going to settle down?”

Now, if you’re Latinx, you’ve heard this phrase before. Maybe too much. It’s the battle cry of immigrant parents everywhere, the reminder that your dating life is scrutinized with the intensity of a Univision soap opera. But in that moment, her question hit a nerve. Because the truth was, I didn’t have an answer. I had no grand romance to report, no engagement on the horizon. I had…nothing.

I smiled, shrugged, and changed the subject. But the truth? The battle I was fighting wasn’t just about being single. It was about feeling like I wasn’t enough—like I was somehow failing to live up to the metric of love and success all around me.

Here’s the thing no one tells you about dating in your 30s, especially with a family that treats relationships like life milestones: It can feel like you’re constantly on trial. But over time, I learned to grapple with this struggle in a way that didn’t just save my sanity—it actually transformed how I approach relationships altogether.

Here’s what I learned after fighting this secret battle with myself.

Chapter One: The Comparison Spiral and All Its Drama

Listen, I’ll admit it. Scrolling Instagram became my toxic habit. There’s always some power couple posting their engagement photos from Santorini or that friend who, in the blink of an eye, went from single to married with three kids. And don’t even get me started on the holiday “We’re so happy together” posts, complete with matching pajamas.

In the comparison game, I was losing, big time.

As someone raised in a Cuban household, I grew up believing that family comes first—always. My parents and grandparents lived that value every day, so why couldn’t I figure it out? I started to think of dating as a series of benchmarks I should have achieved by now, like I was failing a pop quiz everyone else aced. The constant soundtrack in my head sounded like Bad Bunny’s Depresión on loop.

But here’s the thing: Social media victories aren’t the whole story. You might see their candlelit proposal, but you’re not privy to their third screaming match of the week. It wasn’t until I consciously unplugged (okay, snoozed like 12 engagement announcements) that I realized how much those comparisons were eating away at my confidence.

I couldn’t focus on building my own connection if I kept holding it up to filtered versions of everyone else’s.

Chapter Two: Detangling Love from Expectations

Let me tell you something about immigrant families: They’re pros at handing you the Master Blueprint of Your Life™. “By 25, you’ll be married. By 30, you’ll own a house. By 32, we get grandkids.”

I’d been carrying this blueprint around like it was scripture, but instead of giving me direction, it just made me panicky. Every time I didn’t hit a milestone on time, I felt like I was disappointing not just myself, but my family, my culture, my ancestors. (Okay, dramatic. But you feel me.)

The first step toward overcoming this pressure was realizing something painfully obvious: This blueprint wasn’t mine to begin with.

One night in Chicago, where I lived during my writing fellowship, I had one of those eat-ramen-in-bed-while-watching-The-Before-Trilogy marathons (highly recommend). Somewhere in the echo of Jesse and Céline waxing poetic about soulmates, I realized: My life didn’t have to follow a chronological script. No Cuban telenovela plot twists. No family-approved milestones. Just me building something with someone, when I was ready.

Liberating? Absolutely. Easy? Not so much, especially when family expectations persist like background music you can’t quite turn off. But when I started asking myself what I really wanted—not what I was told I should want—I found the noise faded. It’s amazing how quiet things get when you stop living for applause.

Chapter Three: Treat Yourself Like a Good First Date

Here’s a wakeup call I wasn’t ready for: I’d been treating my relationship status like it defined my worth. Raise your hand if you’ve ever felt personally victimized by that thought.

It took me some time—and a firmly worded pep talk from my best friend, Natalie—to realize I’d been pouring all my energy into finding someone, without thinking if I’d even want to date me.

Natalie, being the blunt genius that she is, said: “Okay, imagine you’re on a date—with yourself. Would you swipe left or right?”

Ouch, right?

But she had a point. I’d been so focused on external validation that I’d neglected my own self-worth. So, I started working on becoming the person I’d want to meet (cue the Sex and the City montage music). I took salsa classes on Sundays because why not? I finally committed to finishing the novel draft I’d been working on for three years. I got into running, mostly because I’m too competitive not to win a race against my neighborhood’s overenthusiastic golden retriever.

Bit by bit, I stopped thinking about dating as a “battle to win” or something to check off a list. Instead, I thought about it as a bonus to an already full life.

Chapter Four: Coming Clean

I’d spent so much of my secret struggle pretending everything was fine—and that’s exhausting. Pretending to want what you don’t, pretending to be on the same timeline as your friends, pretending that every awkward family dinner question didn’t sting. Eventually, I got tired of the act.

At a family barbecue last year, my mom raised her eyebrows, tilted her head, and slid one of her classic “calm down” comments across the table. But this time, instead of deflecting with humor, I just let her in.

“Ma,” I said, “Being single isn’t a problem I need to solve. I want to wait until it’s right. And when it happens, I want it to be special. I’m good on my own, por ahora.”

She blinked at me, sighed, and went back to serving congri. But since that day, there’s been less pressure. Not zero, but definitely less. Turns out, opening up about my inner battle didn’t make me weak—it made me feel seen.

The Takeaway: You’re Right Where You’re Supposed to Be

Here’s the thing about love: It doesn’t care about your timeline. It comes when it comes, and in the meantime, we owe it to ourselves to live fully.

That old comparison trap still tries to creep into my brain sometimes—like when my cousin posted another cruise vacation with her boyfriend. But when it does, I remind myself: We’re all on our own path, and sometimes the best relationships come when you’re not chasing them.

If there’s one thing I’ve learned from secretly battling self-doubt and dating pressure, it’s this: You’re never really behind, as long as you’re being honest about what you want. Whether you’re in your 20s, 30s, or 70s, love isn’t a box to check—it’s a whole story waiting to unfold.

Cultivate the life you want first, and everything else will follow. And if you need a reminder along the way, go dust off your copy of The Before Trilogy because Jesse and Céline said it best.

“Baby, you are gonna miss that plane.” You might. But trust me, the next one will take you somewhere even better.