Breaking up around the holidays is never easy. I think that’s because, to most people who celebrate any holiday, these days usually evoke feelings and themes of “togetherness” and “celebration.” But there’s just one holiday that you either love or you hate: Valentine’s Day.

San Valentino, or Saint Valentine, was commemorated as a saint on February 14th, and today’s holiday comes from the saint being associated with a tradition of courtly love. Today you can be sure that you’ll see your Facebook feed full of happily coupled-up friends and family; strangers on dates at restaurants around the city; people frantically buying last minute gifts where you run your daily errands; all such sweet but constant reminders of one thing: YOU’RE SINGLE. Especially if you happen to be, as I am, newly single.

When the break-up is so fresh, that outside of your inner circle of friends, no one else knows it happened — leads to a lot of explaining.

“What are your plans tonight?”

“Soooo, what did ‘so-and-so’ plan for you?”

You stare at them and try not to be too awkward when you say, “Uh, yeah, actually, we broke up.”


While it’s none of your business, I know you want to know.

It’s okay, I’ll tell you.

(And if you're going through the same thing, trust you're not alone!).


Let’s back up to almost exactly 10 months ago when I first met said suitor. I was happily swiping left on just about everyone on Tinder (as you do), when I came upon an impish looking 30-something that caught my eye.

I knew he had to be new at this Tinder thing, because almost immediately he asked me out on a date, instead of the usual “chat for weeks and nothing happens,” which is the Tinder status quo.

We had a great time. Great, I tell you. That first date still goes down in my history as one of the most bizarre/fun ever. He was funny, charming, easy to be with, and we had a lot in common. He was exactly what I needed, and what I was ready for after being separated from my ex-husband for almost a year, and going through a brutally difficult divorce.

The best part of the time we spent together was that it was absent of all of those pressures that normally seem to accompany a romantic relationship — we were casual, superficial, even. Neither of us wanted to settle down or be serious, and with my savage AF working schedule, along with parenting two little boys — I’d been hesitant to put myself out there knowing I wouldn’t be able to/ready for the expectations of being someone’s girlfriend. It was perfect.

Until it wasn’t.


What only my closest friends know, is that I’d considered breaking things off pretty much right away, and several times throughout the relationship. It was a persistent thought that I swatted away like a fly, over and over again as time went on. His insecurities reminded me that I wasn’t alone in my own.

But every time our arrangement (for lack of a better word) seemed like too much or not enough, there came a reprieve in the form of a hearty laugh (to be honest, I’ve never laughed so much with someone), an unexpected adventure, or that addicting impish smile -- that time and again, drew me back in. I'd find myself shutting down any thoughts of ending it.

When the holidays came around, I found myself becoming increasingly disappointed by things I insisted time and time again that I was okay with. I said I didn’t want a commitment. We didn’t have a deep relationship, we had a convenient one, and it was convenient to overlook these things.

With that ambiguity though, comes the inevitable “state of the union” conversation, the one we all have at some point in every relationship. The conversation that starts with, “Are we okay?” I was met with an affirmative response, reminding me that I had to check my insecurities at the door, because he and I were on the same page.

Here’s the thing about insecurities, though. You know how a lot of times the little voice in our head tries to convince us we’re not good enough, thin enough, funny enough, WHATEVER enough, and we know we should push that voice away? Sometimes, just once in awhile, that little voice in our head knows something that our heart doesn’t want to admit: That things are just not right.

While we may have been on the same page, we weren’t reading the same book. It's easy to tell yourself that "this doesn't mean anything." What's harder, is talking yourself out of genuine feelings of affection that tend to grow over time. Here's an embarrassing bit (for me) --my blinders were on so tight, he had tried breaking up with me over a week ago, and I had totally missed it. 

Our status, or lack thereof, was solidified a few days later, just in time for the Mother of all Hallmark holidays.


I'm most sad about losing a friendship, than I am a romantic relationship. I’m confident that we treated each other with enough respect and dignity, that someday when we inevitably run into each other (it is WNY after all....), we’ll be able to smile, look each other in the eyes, say hello, and it won't have to be awkward or weird. Not all of the relationships I’ve experienced in my life have ended this way, but what I learned about myself in this particular process was that IT’S OKAY to say what you mean and do what you say. IT’S OKAY that you want to be loved a certain way, and it’s just as okay for someone to tell you that they’re not able to give you what you want. The more honest we are with our time and the people in our lives who share it, the easier it is to get over losing something that wasn’t really meant to be in the first place.

And so I wish you all a very happy and honest Valentine’s Day, sharing it with whomever you may love.