When I was in fifth grade I had a huge crush on Emily Richmond. We were ten years old at the time but I was pretty certain we were going to get married, have like 400 babies, and live happily ever after. Trust me, it all made complete sense at the time. I figured Valentine’s Day was the perfect stage for me to profess my undying love and admiration. So while I was dropping Valentines that said “I Choo-Choo-Choose You” into the paper boxes taped to the desk of the rest of my class, Emily got a single rose attached to a hand written poem. The move was bold – potential for embarrassing failure was high to quite high, but I stood at her desk completely expecting her to be deeply smitten. And she was—only with my best friend Corey Lewis who had beaten me to the punch with a box of Russell Stovers and a card that said “I Choo-Choo-Choose You.” Valentine’s Day can be a fickle mistress.

That prepubescent romantic has grown a bit more cynical over the years, and these days Valentine’s Day is less about love and romance and more about “things.” Flowers, chocolates, dinners, bears that say “I love you,” when you squeeze them, the delicious conversation hearts that go on sale for $.99 a bag on February 15th. An entire aisle of Duane Reade turns pink and red for a month, acting as a constant reminder to come up with something more clever for your girl than a bear that says “I love you,” when you squeeze it.

The fact is that for the average American male the lead up to Valentine’s Day is filled with overwhelming dread. Not like zombie apocalypse dread, or even man eating robot dread—as men we face those fears daily—but rather the kind of dread that comes when you have to feign interest in a day because it means a lot to someone we care about and want to see happy.

It’s not that we don’t care. It’s just as far as the day itself goes, February 14th means no more to us than Arbor Day or the 8th of July—except that if I get a girl flowers on July 8th the lack of expectations elevates the entire experience to something truly sweet and noteworthy. Doing it on Valentine’s Day is expected—possibly even underwhelming. It’s a day of high risk and low reward and the expectations can be daunting.

Sometimes the fear isn’t just not doing enough; it can also be doing too much. What do you do for the girl that you occasionally hook up with when you’re drunk? Is that flower worthy, or can you get by with a nice card?

The irony is that Valentine’s Day is actually like the day of atonement for bad boyfriends. Each flower and glass of champagne is paying for that night out with the boys, or a missed anniversary, or any general act of bad boyfriendness perpetrated over the last year. If you’re spending the other 364 days letting the person you’re with know how amazing they are then February 14th becomes just another day on the calendar.

But the institution endures and come the 13th the pink and red clad aisle at Duane Reade will be packed with all kinds of dudes frantically searching for a bear that says, “I love you,” when you squeeze it and $3 bags of delicious conversation hearts. The reason?

Because whether it’s Arbor Day, Valentine’s Day, or any other day we want the girl we’re with to be happy—and making that happen is worth the dread.