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I’m either dating the coolest girl in the world, or I’m in for a world of pain come this Wednesday.
When Jennie told me that she didn’t want to go out on Valentine’s Day, I immediately sensed a trap. No matter her protests of the holiday being overrated (it is), with forced romanticism (too true), and overcrowded restaurants serving limited menus at exorbitant prices (preach, baby!), I was suspicious. No girl feels this nonchalantly about the most Instagrammable holiday of the year, and I know my girl is no different.
But she continued to follow this script, assuring me that she was content to have a Galentine’s Day in solidarity with her single friends on the 14th, instead of a romantic/pressure-filled night with me. It sounds great, and we’ve already coordinated something special for February 13th where we can spend the night together with drinks, a reasonably priced dinner, and laughter at the poor souls engaging in the rat race the following night. Yet I’m still wary that this could be a trap.
You see, I know Jennie has a history of being cooler than the other side of the pillow, but I can’t fight this feeling that she might be expecting something bigger. It’s our first Valentine’s Day as a couple; that comes with a lot of pressure. This is also our first major holiday as an official couple unless we’re counting Martin Luther King Day. How I handle this holiday can have vast ramifications on the future of our relationship. If I flub this, I could be in the doghouse for months. If I kill it, I’ll be swimming in good boyfriend vibes forever. The question is can I trust her assurances that she doesn’t want to take things too seriously?
Let’s say I am being bamboozled, that this is some giant test concocted by her and her friends to see how well I do in the “significant other mind-reading” skill. If I do the standard guy move and take her words at face value, I’m going to look like I don’t care. But if I go the other way, and blow my load when she really does want the simple night, now I’m the asshole because I’m making it seem like she is the one who doesn’t care. It’s like a 4-dimensional Mexican standoff and it’s frying my brain.
On top of the mind-games (or non-mind-games…gah!) there is the baseline question of how much is expected for a first Valentine’s Day in general? I mean, this is our first romantic holiday; it’s going to set the baseline for all future V-Days, birthdays, Christmases, anniversaries, and the like. If I play it conservatively, she’ll think I don’t give holidays their proper due. But if I go all-out, I’ve set myself an impossible standard that I can’t possibly hit again.
Is chocolate too much? Flowers? Stupid cute little trinkets that go with chocolate or flowers? Jewelry? Is the restaurant I picked nice enough? Too nice? Should I pull the surprise gift move, or is that too big a move?
This is the D-Day, the Super Bowl, the final showdown of dating. I’ve been steeling myself for this for the last two months, mulling my options over and over, wondering how this is going to go down. Now, the plan is in place, unfurled in my mind’s eye like Kevin McCallister’s plan of attack to foil the Wet Bandits. Vetted by my friends, planned to nearly the minute, it’s ready to go, but far from a sure success. I have a ballpark of what is expected of what is expected, what might be too much or too little. But of course, as I am one to do, I’m going to overanalyze the shit out of the day.
To all you other poor souls, embarking on your first Valentine’s Day as a couple with no clue what the expectations are or how you’re going to deal with whatever awkwardness that might arise good luck. I wish I had some words of wisdom, some kind advice, or assurances that it will all work out. All I can say to you is to do your best to show that special someone your true feelings and your true self. 2018 is the year of shooting your shot. That doesn’t just apply to asking out the pretty girl at work or the cute guy at the gym. It means being willing to let yourself be yourself, and go for someone that matters. What better day than February 14 to take that shot. .