Valentine’s Day has always arrived with a tone that is half celebration, half inventory. Every February, the world seems to ask the same questions: Are you progressing correctly? Are you paired off, promised, planning? The holiday turns intimacy into something public, measured by reservations made in advance, flowers delivered on time, and the unspoken assumption that love should be visible, legible and ideally moving toward something permanent.
For years, I assessed myself against the red roses crowding grocery stores, the engagement rings slipped into champagne glasses, the social media posts that broadcast she said yes! like a chorus. Each image felt like a checkpoint, a reminder of where I was supposed to be and how closely my life should resemble the ones unfolding everywhere else.
In my 30s, Valentine’s Day arrived with a particular kind of anxiety. The stakes felt impossibly high. Friends were getting engaged quickly, being set up with intention, openly talking about husbands and timelines. Dating stopped feeling exploratory and started feeling evaluative. Valentine’s Day became a moment to take inventory: not just of a relationship, but of its future.
Every February, if I was seeing someone, the same questions surfaced. Was this someone I could imagine marrying? Did I want to build a life with him? Could I see him as the father of my children? Valentine’s Day seemed to gather those thoughts and place them gently, but insistently, on the table.
No one was asking me for answers directly, yet I felt the questions everywhere. Valentine’s Day never asked whether I was content. It asked only whether I was moving forward.
One year, I was dating someone who checked all the expected boxes. As Valentine’s Day approached, it began to take on an unspoken gravity. When he made a reservation at a restaurant where every table holds a single rose in a narrow vase and the menu is fixed, whether you like it or not, I felt a tightening in my chest.
Throughout dinner, I found myself less focused on what he was saying and more on the silent checklist running through my head. He was thoughtful and attentive; the kind of boyfriend I should want. But beneath the candlelight, I felt like I was trying to talk myself into something.
I dated earnestly through my 20s and 30s. I showed up. I tried. I wanted to commit to the kind of life everyone else seemed to fall into so easily. But under the effort and evaluation was a steady truth I eventually had to face: I never met someone I felt certain I could start a life with.
No matter how promising someone seemed at the start, I would eventually realize I couldn’t picture myself sharing a future with them. And I couldn’t force myself toward a life I didn’t feel fully, unmistakably sure about.
For a long time, I mistook that refusal as a personal failure.
The shift came slowly, through repetition — not one realization or a single turning point, but a series of small moments. Unanswered texts that brought more relief than disappointment. Second dates, I didn’t push myself to schedule. Conversations that faded without drama. Endings that hurt, but also felt clarifying.
I began to notice patterns —not just in the people I dated, but in how I responded: what felt like effort versus what felt like ease. Over time, I stopped treating resistance as something to overcome and started listening to it.
I started volunteering. I took up Pilates. I returned to writing. I traveled internationally, alone and with girlfriends. I joined book clubs, learned new recipes and even took the risk of starting my own business. As my life expanded in these ways, I stopped looking to romantic love as the thing that would complete me.
Romantic disappointments began to lose their sharpness. Bad dates and breakups stopped feeling like evidence that something was wrong with me and started to feel more like part of a learning curve. Each ending clarified something — about what I wanted, what I didn’t and what I was no longer willing to override in myself.
There was a subtle shift in realizing that not every connection was meant to work, and that walking away didn’t have to mean I had failed. When I thought about the men from my past I’d once pictured a life with, I felt relief — not as a judgment of them, but because I’d listened to myself when it mattered. Self-protection softened into self-respect, and what once felt like rejection slowly began to register as self-trust.
One year when I was single, I hosted a Galentine’s Day dinner that was, without question, the most fun Valentine’s Day I’d ever had. I invited a handful of girlfriends over, women who had sat with me after breakups, celebrated career wins, and witnessed the unglamorous middle parts of me finding my footing. I put out charcuterie boards. We opened wine, passed chocolates across the table and had long conversations about work, heartbreak, money, ambition, and the small ways we were all learning to follow our own instincts. The night was easy and loud and full — no posturing, no performance, no decoding what anything meant.
Photos Courtesy Of Jillian Sanders
In my 40s, Valentine’s Day no longer feels like a test I have to pass. It feels like a mirror ― and I know how to look into it honestly now. I see a woman who didn’t rush toward a life she wasn’t certain she wanted. Someone who learned that resistance isn’t always fear or avoidance; sometimes it’s clarity.
I still date, but it’s easier now. Lighter. Less freighted with outcome. I’ve learned that there are many ways to build a happy, meaningful life, and none of them hinge on romantic love.
These days, Valentine’s Day brings me genuine joy — not because I’ve opted out of love, but because I’m surrounded by it. In friendships that feel steady and reciprocal. In family bonds that have deepened with time. In work that fulfills me. In a life that feels full, even without the shape I once assumed it needed.
This Valentine’s Day, I’ll grab dinner with a friend, not a candlelit prix fixe, but something casual. I’ll come home, light a candle and read a book. I’ll text more people than usual just to tell them I love them.
There will be flowers on the table. They’ll be from me.
The holiday has taken on an entirely different meaning now, not a measure of what’s missing, but a reflection of what’s already here.
Jillian Sanders is a writer based in Denver. You can find her at www.jilliansanderswrites.com or @jilliansanderswrites on Instagram.
Do you have a compelling personal story you’d like to see published on HuffPost? Find out what we’re looking for here and send us a pitch at pitch@huffpost.com.
