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.

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Time to Take My Own Advice (Trying To, Anyway)

So, here's what I'm practicing as Valentine's Day approaches (with varying degrees of success, of course):

I'm allowing the anticipation. Instead of pushing away the anxiety about the approaching date, I'm acknowledging it. Pushing it away will only make you think about it more. If I told you that I wanted you to think about anything except for a purple duck for the next two minutes, what would you end up thinking about? Probably a purple duck… So, let’s give it the space that it will take up regardless of whether or not we give it permission. Yes, this sucks. Yes, this is hard. Yes, it's uncomfortable. No, that doesn't mean something is wrong with me or my healing process. The dread I'm feeling is data that is telling me this milestone matters, and that's okay.

I'm rejecting the comparison game. Social media will be insufferable (insert eyeroll) on February 14th. There will be engagement announcements and couple photos and expressions of grand romantic gestures. And I'm making peace with the fact that my day will look nothing like those highlight reels. It will also be different than Valentine’s Days in my past. Different doesn't mean less-than.

I'm building my own experience. Rather than treating Valentine's Day like something to survive, I'm asking myself what would make the day feel meaningful on my own terms. This year, I’ll be celebrating other versions of love in my life by going bridesmaid dress shopping for my best friend’s wedding. And as ironic as it seems, I’m actually looking forward to celebrating my platonic soulmate and enjoying a little bit of girlhood together. For you, maybe that's dinner with friends who are also single. Maybe it's finally starting that book you've been meaning to read. Maybe it's absolutely nothing special, and that's fine too.

I'm practicing self-compassion. If I had a client sitting across from me, preparing for their first Valentine's Day after a major relationship loss, I'd tell them to be gentle with themselves. I'd remind them that healing isn't linear, that setbacks aren't failures, that feeling sad doesn't erase progress. I'm trying to offer myself that same kindness. There's a line from Taylor Acorn's song "Birds Still Sing" that's been playing on repeat in my head lately: "Our moon moves in phases, so give yourself a little grace." Maybe you have a song lyric, a piece of writing, or advice someone once gave you that could help remind you to practice some self-compassion.

My Mother Calls These "Growing Pains"

Here's what's wild about personal growth…it's rarely comfortable in the moment. We celebrate growth in retrospect, when we can look back and say, "Look how far I've come." But while you're in it and you're crossing those thresholds for the first time? It mostly just feels hard.

This Valentine's Day, I'm going to wake up single for the first time in 14 years. I'm going to feel whatever comes up: sadness, relief, grief, freedom, anger, peace. Probably all of it, in waves, throughout the day. And I'm going to trust that getting through this first is exactly the work I'm meant to be doing right now.

Because here's the truth beneath all the professional knowledge and therapeutic frameworks: Sometimes being highly ambitious means being ambitious about your own healing. It means setting a goal not for productivity or achievement, but for simply being present with your own experience.

If you're also bracing for a difficult first this Valentine's Day, or any first for that matter, I see you. We're all just doing our best to show up for our own lives, one difficult first at a time. You're not alone in the anticipation, the anxiety, or the work of crossing that threshold. If you’d like a little extra support from someone who truly gets what you’re feeling our Shift Collab therapists are always in your corner 😊

Olivia

Vander Vloet

she/her

Olivia is here to support you with ADHD, the stress of work or school, tough family dynamics, big emotions, and struggles with substance use.