Valentine’s Day Is an Abandoned Field of Landmines & Other Hot Takes From Our Matchmaker

I am a matchmaker and, somewhat ironically, a total grinch about Valentine’s Day. I think this Hallmark holiday is bad for absolutely everyone: the unattached, casual daters, early relationships, couples, throuples and everyone in between.

It’s pretty obvious how Valentine’s Day can be 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.

In this season, the world ‘single’ is flung at the unattached like a grenade all month long. While identifiers like “fat” and “queer” have been reclaimed and worn with pride, the world ‘single’ is still used like a four letter word. Why? It seems to me that singleness is viewed as a temporary, unwanted state of being. This ignores the fact that singledom can be a conscious choice, an identity all its own. Celebrities like Tracee Ellis Ross and Fran Drescher have described 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 all dating choices, full stop.

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 landmines. Enter at your own risk.

People in relationships that fall outside of conventional binaries 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, or the cringy expectation to buy flowers or write a heartfelt card? 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. This February 14th, there is also a tangible alternative in the form of a shameless plug: Valentine’s Day Volunteering, an annual event at Tribe 12 where we create a space for anyone, single coupled or anything in between, to get together and do some good. This year we’re partnering with Free Minds and Repair The World for a virtual opportunity to read and respond directly to the words of incarcerated poets.

And listen… if you are a lifelong worshipper of Valentine’s Day with family traditions or fond memories 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.


Danielle Selber is one of the in-house matchmakers at Tribe 12, connecting young professionals who are dating in Philadelphia’s Jewish community with each other and the community at large. To view our calendar of Valentine’s-adjacent events, visit


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