Surviving Our Most Awkward Holiday – Valentine’s Day

Damn, dating is awkward, especially in Door County – we’ve covered that (Volume 17 Issue 35 “Three Dates in the Door”). But when the sun comes up on the most sacred day of love, situations have potential to become really, really awkward.

I’m a young woman with only a handful of Valentine’s Days behind me, yet somehow I’ve managed to create or be a part of many an awkward Valentine’s Day. It all started with not admiring my admirer…

My first crush: a tall baby-faced 15-year-old named Dustin. He listened to Garth Brooks. He watched Friends. He cheated off my algebra homework. He once spiked a basketball in my face when we played one-on-one. I adored him.

Then came Valentine’s Day and that coveted note (only on February 14) to visit the school office. The straight-faced receptionist wearing a fuzzy red sweater handed me a small bouquet of pink and red roses and carnations. The card read, “Happy Valentine’s Day – From your secret admirer.”

I knew he sent the flowers. I knew in the depths of my heart this was true love. We would hold hands in the school hallways, eat our hot lunches at the same table, and complete algebra homework after school in my bedroom, alone. Well, with the door ajar – Mom prohibited time alone with boys until we were 16.

Beaming, I called Mom from the payphone to tell her I had my first boyfriend.

“Mom, he sent me flowers!”

“Who did?”


“Honey, what does the note say?”

“From your secret admirer.”

“Sally, I sent those flowers.”


“I’m so sorry. I though it’d be cute.”

I cried in a bathroom stall. Dustin never professed his love, which is for the best – according to his Facebook page he now likes Metallica and Glee. That’s just not going to work.

Then there was that memorable Valentine’s Day shift I waitressed at Porta Bella in Madison, an Italian restaurant with dim lighting and gaudy décor. One couple ordered tiramisu before dinner (how wild), another appeared to break up (mascara was running down the poor girl’s cheeks while the boy shifted uncomfortably in the red velvety booth), and another included the recent ex-girlfriend of my fellow waiter. Awkward. My co-worker punched a brick wall and kept repeating, “You don’t disrespect me like that. How dare she disrespect me like that.” He grew more upset when I forbid him to spit in their entrees.

Then there were those after-work Fat Tires and Spotted Cows with a boss, who, God bless him, felt he should keep my thoughts from rerunning a recent breakup on the day of love. After one or two pints in the dingy bar, tears flooded my eyes and a dramatic monologue sprang forth, something like, “My heart hurts…I feel so disposable…He’s going to regret it…I’m like the nicest, funnest person ever…I just don’t know if I can stay here…I think I should move away.”

“Well, let me know what you decide – the sooner the better. I’d have to hire someone to fill your spot.”

“I’m not quitting.”

“What are you saying then?”

“I’m just thinking out loud.”

Awkward. Word of advice: think out loud with someone who doesn’t sign your paychecks.

In conclusion, to avoid Valentine’s Day awkwardness, keep it simple – expectations, plans, and interactions with fellow human beings. The holiday, which originated to honor a martyr, has now become the least single-friendly day of the year. So for those of you who suffered a recent breakup, or simply suffer from low self-esteem, I say take up that pint of cookie dough ice cream and don those stained sweatpants. It’s best for everyone involved.

If you happen to call someone ‘mine,’ expectations can be so high that the wrong gift [a stuffed teddy bear instead of a diamond engagement ring] or wrong sentence [“Wow, our waiter is so hot”] can launch a lady into a tizzy of tears and a man to the brink of an emotional breakdown. Soon you’re having “the talk” over chocolate raspberry cheesecake and flutes of champagne. Awkward. I suggest exchanging homemade Valentine’s and high fives; there’s not a lot of room for failure.

“I love love,” my friend Lindsay once professed. As do I; I also love that love creates some pretty awkward moments.

Happy Valentine’s Day!