My Single V-Day Experiences: The Good, the Sad, & the Unexpected

Single on V-Day? Been there, done that–every way possible.

There were the years I cried because I was STILL single, wondering if I’d ever get off the situationship rollercoaster and finally find my person. The ones where I walked past the hosts of couples holding hands, canoodling, exchanging flowers and love notes, feeling like I was the only one left out of the annual Hallmark holiday lovefest.

Then, there were the Galentine’s years—where I turned heartbreak into good times with my single BFFs. Whether it was cocktails, a fancy dinner, or a spa day, the focus was on celebrating us. No pity parties, just a reminder that love comes in many forms—including friendships that last through every bad date, hollow hookup, and ghosted text.

Of course, there were also the quiet Valentine’s Days. The ones where I embraced the single life, curled up with a cozy blanket, an Oscar-nominated flick, and ordered in my favorite comfort foods (e.g., in San Francisco… the veggie quesadilla from Papalote, or the wonton soup from Alice’s, or the Panna or Funghi pie from Pizzeria Delfina; and in DC…. shack burger, fries, and a black & white shake from good ole’ Shake Shack). Because if couples get boxes of chocolate truffles, why shouldn’t I treat myself?

But the most unexpected Valentine’s Day? The year I moved to DC, I actually agreed to a first date on February 14th. Though it was a Tuesday and the guy didn’t even realize it was V-day until I mentioned it. Part of me thought this would either be a disaster or a great story. And honestly? It was… fine. Not a love match, but not the worst way to spend the evening either. We had decent Thai food, and while walking to the metro, we spotted a motorcade in front of Jose Andres’ Minibar, where the Obamas seemed to be dining for V-day! As a newbie to the District, I felt compelled to wait with the crowd that had gathered on the corner for a chance to see the first couple emerge. My date was not so interested, so we parted ways. Standing there in the rain with a bunch of strangers reminded me that Valentine’s Day isn’t just for couples—it can be a fresh start, a fun night, or just another day, depending on how you frame it.

So, if you’re single this Valentine’s Day, I’ve been where you are. And my advice? Feel your feelings, make your own memories, and remember—your love story is still unfolding.

XO,

Lisa