The Problem With Valentine’s Day, According To Our Matchmaker

I am a matchmaker and, it has to be said, a total grinch about Valentine’s Day. I’ve come to realize that this Hallmark holiday is bad for absolutely everyone: the unattached, casual daters, early relationships, couples, throuples and everyone in between.

The original sin of Valentine’s Day is that it is, at it’s heart, a giant commercial ploy. Worth on V-day is measured by dollars spent (see: pink explosion in chocolate aisle at the drugstore). If you buy the slightly smaller heart shaped box o’ chocolates, will her friends convince her you don’t actually love her? If you buy him a watch this v-day, will you have to buy him jeweled cufflinks next year, and a Ferrari the year after that?? These considerations are ridiculous, and yet the recipient of your gesture will most likely judge its worth by $$$ too, influenced by whatever pop-culture societal-norm Kardashian-sister soup we’ve been fed our whole lives.

Valentine’s Day can be particularly brutal for someone who is single, whether by choice or circumstance. Lovers of romcoms may know that the day after Valentine’s Day is informally known as “Singles Awareness Day” which abbreviates to “S.A.D”. That pretty much sums up how society views singles on and around v-day — a subgroup to be pitied, scorned or both.

That type of noxious thinking oozes all the way through February. Magazine covers scream “Top 27 Unexpected Places to Meet Your Next Bae!” Your most obnoxious coupled friend will inevitably post an insult-as-compliment like, “single friends, don’t despair — your soulmate is OUT THERE!!!” Tis the season to lob the word ‘single’ at the unattached like a grenade all month long. What a heartwarming tribute to the month of love!

Have you noticed that identifiers like “fat”, “queer” and even “nasty” have been reclaimed and worn with pride, but the world ‘single’ is still used like a four letter word? Singleness is a temporary, unwanted state of being, the thinking goes — so what’s there to reclaim? This ignores the fact that singledom can be a conscious choice, with celebs like Tracee Ellis Ross and Fran Drescher describing it as a decision made from a place of empowerment rather than necessity. That outlook is equal parts badass and totally legitimate. It’s a reminder that when a friend tells you they are single by choice, don’t greet them with condescending puppy eyes, and definitely don’t set them up your cousin’s boss’s neighbor. Be a partner and champion of dating choices, full stop.

Hot take: Valentine’s Day is also really, really bad for couples at any stage. Budding romance? Here’s your first big test about how serious you are, but careful not to come off as clingy and desperate or cheap and unavailable! Engaged or newlyweds? Prove yourself worthy of my endless love with an over-the-top grand gesture that I will judge you against for the next decade! Married for 50 years? Don’t you dare recycle old ideas or give a gift that is purely sentimental — am I worth that little to you?? You see how this can make your head spin. In a couple, Valentine’s Day is less of a holiday and more of an abandoned field of land mines. Enter at your own risk.

People in relationships that fall outside of conventional relationship binaries and iterations have to navigate even more complexity. For those who identify as asexual (having little interest in or desire for sexual activity) or aromantic (lack the feeling of romantic attraction), the typical trappings of Valentine’s Day might be irrelevant or downright offensive. Why should you have to endure endless condom commercials and diamond ads during the Super Bowl; the cringey expectation to buy flowers or write a heartfelt card; lovey-dovey couples making out on your crosstown bus? The message is clear: if I experience attraction or romance differently, I am still subject to the unwritten, arbitrary rules of Valentine’s Day. Gross.

Like with other made up holidays (…really IHOP, National Pancake Day? seriously?), the only way to win the game is not to play at all. Regardless of who you are or who you date, consider this an invitation to opt out of all things Valentine’s. That includes spending money, giving gifts, planning surprises, booking trips, fancy dinners, or obligatory sex (we’ll save my bottled-up fury about that for another day).

And listen… if you are a lifelong worshipper of Valentine’s Day with family traditions and fond memories somehow attached to it, I get it. I won’t ruin the February version of santa for you. As long as you’re the one deciding whether or how you celebrate, all choices are healthy choices… except maybe that giant heart-shaped box of 100 chocolates that goes on sale on February 15th. You should probably put that back on the shelf.


Danielle Selber is Tribe 12’s in-house matchmaker, connecting young professionals who are dating in Philadelphia’s Jewish community with each other and the community at large. To view Valentine’s-adjacent events or book a virtual coffee date visit