Why Are Big Dates Never Any Fun?
After My Botched Anniversary Date, I Asked An Expert

Let me set the scene: Chicago. My anniversary night. We both get off our respective restaurant shifts utterly exhausted. I put on a skirt that does not fit right and slather on makeup that has fully melted off my face by the time I rush into the restaurant (thank you, Midwestern summers). We sit down on the patio at a lovely spot both of us can absolutely not afford and I already catch myself wondering why big date nights are never any fun. I am hell-bent on making this one different. We order a bottle of crisp white wine that I am physically unable enjoy because of the severe dehydration that comes from a day of waiting tables and shoveling hash browns into my mouth next to a 140-degree back kitchen. We realize halfway through dinner we were late to our second stop, a concert we had bought tickets to months ago, so we scarf down the rest of our food and sprint. No meaningful conversation has taken place thus far in the night. When we arrive at the venue, I realize I do not have my ID and am barred from entering. We both give up our tickets, get in an Uber back home and I can feel tears welling up in my eyes.

You might have your own version of this night, an evening with blueprints so perfect that in theory it would have (1) raised the bar for all your future anniversaries and (2) set the tone for the blissful year ahead. In reality, it was lackluster in its best moments and profoundly stressful in its worst moments, right? The Big Date Night™ is a complicated endeavor and I know I am not alone. To figure out why it so often turns into an absolute mess, I enlisted the help of therapist and dating coach Kimberly Seltzer.

“Holidays (anniversaries, birthdays, Valentines Days, etc.) have become so sensationalized,” Seltzer tells me over the phone. “If you think about our grandparents’ era, they didn’t have social media, so holidays were more geared towards each other and the couplehood. What I’m seeing happen now is there is more focused on what is being done for the holiday rather than the real connection of the couple.”

Cutesy social media posts tend to spike around these occasions, with an endless Instagram feed of flowers on Valentine’s Day and kisses on New Year’s Eve. It can feel like you need to do something glitzy or there really is no point in celebrating at all. While anniversaries, birthdays and holidays can be a lovely time to shower your person with love and plan an extravagant evening, there is an undeniable pressure when you put unreasonable expectations that this one night will turn it all around, reignite the flame, and s et the tone for the next year of your life and your relationship…keep reading →