When Valentine’s Day Marks a Big First
Valentine's Day is fast approaching, and I'm doing something I haven't done since I was 15: preparing to spend it alone. Between a high school boyfriend, a rebound relationship, and 8.5 years with the man who became my husband, I haven't been single on February 14th in fourteen years. Now at 29, after six months of separation from my ex-husband, I'm staring down the second half of what I've been calling The Year of Firsts. And this particular first feels heavier than most.
Here's the thing: I'm a therapist. I literally help people navigate breakups, separation anxiety, and the emotional landmines of post-relationship life for a living. I know the research. I understand attachment theory. I can enthusiastically tell you all about the Four Tasks of Mourning and why I prefer them over the Five Stages of Grief. And yet, sitting here with my own calendar counting down to February 14th, all that professional knowledge feels remarkably… inadequate.
A Little Too Ironic
There's a weird irony to spending your days guiding others through difficult life transitions while simultaneously living through your own. In session, I confidently tell clients that the anticipation of a triggering event is often worse than the event itself. I explain how our brains catastrophize, how we project meaning onto arbitrary dates, how Valentine's Day is ultimately just a Tuesday with better marketing. I say these things with conviction because I believe them. They are facts, and I am a woman of science after all.
But knowing something intellectually and feeling it emotionally? Those are two entirely different experiences.
I’ve spent the past few months realizing how oblivious I was to the emphasis marketing places on being part of a couple. Halloween has the challenge to find the best couple’s costume. Christmas is what I like to call “Proposal Season”. Do you know who you’ll be kissing at midnight on New Year’s Eve? And just when you think you’re getting a break from it all…the Valentine's Day industrial complex kicks into high gear! There are all the restaurant promotions, the flower shop displays, the rom-com marathons, the heart shaped jewelry. And each time when I notice that familiar tightness in my chest or lump in my throat, I find myself doing exactly what I tell my clients not to do: I minimize it. "It's just a day," I tell myself. "You'll be fine."
Except that dismissing your own emotional experience is terrible advice, and I know better.
Why Firsts Hit Different
What I'm learning, or rather, what I’m relearning is that firsts matter. Not because they're objectively more difficult than second or third or 30th experience of the same thing, but because they represent a threshold we have to cross. This will be my first Valentine's Day in 14 years where I won't receive a card with someone else's handwriting. The first time I won't have dinner reservations to coordinate or a gift to wrap. The first time the default answer to "What are you doing for Valentine's Day?" is simply "Nothing."
And that threshold I’m crossing isn’t just about Valentine's Day. It's about the acknowledgement that my life has fundamentally changed shape. That the girl I was at 15, eagerly celebrating her first Valentine's Day with a boyfriend, couldn't have imagined that at 29, she'd be here, navigating the dissolution of a marriage and rediscovering what it means to be just herself.
Now, if you’re driven by achievement like I am, you probably struggle with firsts. We like to have a plan. We optimize, we strategize, we execute. But grief and transition don't follow a project timeline and there’s no productivity hack for healing. Unfortunately, you just can't optimize your way through heartbreak.



















