Valentine's Day Survival Guide for Singles

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February 14, 1929. Chicago.  Chilly winds whip through the Windy City.  Chicagoans find refuge in clandestine speakeasies, knocking back bootlegged, 100-proof “coffees” in soft yellow lamplight.  Flappers and Flaming Youth, Jazz Babies, if you will, boogie the night away, smoking their cigarettes and basking in the feeling of rebellion against their parents’ traditions and values. 

And yet on this cold winter night, against the backdrop of a socially robust 1920s Chicago, something dark and sinister hangs above like an ominous cloud. Far more baleful than the infamous St. Valentine’s Day Massacre ordered by Al Capone.  Perhaps more tragic than the Stock Market Crash that would go down only a few months later.  This wicked travesty? The fact that on that night, thousands of people in Chicago and beyond were spending Valentine’s Day all alone. No one to whisper sweet nothings in their ears. No one to Fox Trot them to the bedroom. And, certainly, no one risking jail-time to spoil them with a nice bottle of inky Malbec. No wonder Capone was feeling rather malicious on this particular day.  He too, must have been dateless on Valentine’s Day!

This, my friends, is the dark and gloomy tale of Singles Awareness Day, and it lives on even today.

Fast forward almost a century and S.A.D. still haunts singletons each February, drowning us in doilies, candy hearts, and greeting cards.  We’re incessantly reminded that “every kiss begins with Kay,” some chump went to Jared, and the Overstock.com lady is still living the good life (a gorgeous husband, cute kid, diamond earrings, breakfast in bed, her favorite flowers and a spot on TV. Some broads get all the luck.) To make matters worse, it’s virtually impossible to get a dinner reservation anywhere decent.  Your only real option is a bland Lean Cuisine, sappy movies and a handle of cheap vodka, all by your lonesome.  Right? Wrong!

Though I absolutely loath Valentine’s Day with the fire of a thousand suns, I’ve vowed never again to wallow in self pity.  I’ve been there, done that, and it wasn’t pretty.

February 14, 2005: Another heart-wrenching, soul-shaking break-up with my on-again, off-again college sweetie the night before.  As my roommates readied themselves for the impending red roses, saccharine-sweet greeting cards and fancy dinners with their boyfriends, there I sat on our big blue couch, alone, teary, and ready to die. With a box of tissues, a large Papa John’s pizza and the full intention of devouring the entire thing by myself, my Valentine’s Day was looking pretty bleak already. Until the doorbell rang.  It was Roommate #1’s beau, with a bouquet of roses in one hand and two bags of groceries in the other.  Change of plans! He had decided to cook her a romantic candlelit dinner at our apartment instead. To avoid committing murder and the inevitable needle in the arm, I packed up my things and stormed out of the house to spend Valentine’s Day…. at my parents’ house. How lame. Never. Again.

Since that dreary night, I’ve made a promise that Valentine’s Day would never be spent wallowing or whining again, whether I’m on my own or seeing someone special.  From game night with the girls to dinner out with friends to rock star dance parties, Valentine’s Day has been pretty, well, fun, actually.  A couple of years ago on S.A.D., I even spotted NBC12’s Jim Duncan at CVS on my lunch break. Who NEEDS a Valentine when you’ve seen that hunk in real-life?!

Valentine’s Day, the kingpin of “Hallmark holidays,” has long been considered a love-it-or-hate-it kind of situation.  This year, chuck out all those pesky negative thoughts and embrace the holiday as a chance to let loose, have fun, and maybe find love when (and where) you least expect it!

1.    Road Trip!: The gods must be smiling down upon us this year, Singles, because Valentine’s Day falls over a long-weekend.  Thanks to Mr. Washington’s b-day (better known as Presidents’ Day,) most of us have Feb. 15 off.  Since you’ve got an extra day to celebrate your fabulousness, why not be a weekend warrior? Grab a few friends, pack your bags and plan a road trip somewhere spontaneous and fun.  If you do it right, you won’t even remember that it’s Valentine’s Day at all.  Bon voyage!

2.    Dinner Party: With all of the cooking-centric shows abounding on television these days, we collectively have developed a little bit of foodie snobbery.  Put this to good use and go all Tom Colicchio on Valentine’s Day.  Invite friends to bring over their favorite dishes and bottle of wine, throw on some Etta James and enjoy a homemade feast with loved ones.

3.    Horror Fest: Nothing says “I love you” like a bit of blood, guts and decapitated heads, right?  Throw an anti-love movie marathon.  Rent your favorite horror films, pick up some Vampire wine and popcorn and be prepared to be scared.  The nightmares will distract you…muahahaha.

4.    Spa Day: Richmond has an abundance of amazing spas (Salon Vivace is a personal favorite.)  Take advantage of this fact and book a spa day, complete with massages, facials, manicures and pedicures.  Bring along a friend for added camaraderie.  Valentine’s Day is great day to pamper yourself.  Couples shouldn’t be the only ones getting spoiled on this day.  You deserve it, too!

5.    G.N.O.: Plan a Girls’ Night Out.  Pick up Sticky Rice To Go-Go, rock out to Miley, then paint the town red with your best girls.  Valentine’s Day is a great excuse to go out with your girlfriends (not like we need an excuse), and it’s actually the best night of the year to go out!  You might get lucky in love, even if you’re not expecting it.  So put on your sexiest Little Black Dress, slip into your highest red heels and slap on some matching red lipstick, Sassy.  Dance, flirt, laugh, and have fun!

Though in the past, spending Valentine’s Day “alone” might have been as pleasant as, say, taking an acid bath, this is your year to say “sayonara” to Singles Awareness Day. This Valentine’s Day, embrace being on your own and independent, and make the most of Singles Appreciation Day.  Being in a couple is not always what it’s cracked up to be, especially on Valentine’s Day.  Hey, at least you don’t have to smile through gritted teeth when you get the crotch-less panties gift. Just sayin’.

Caroline is a 25-year-old single girl living in the Fan. She works in PR for a non-profit by day and moonlights as Richmond.com's dating columnist. To learn more about Caroline visit http://carolinesplate.com, on Twitter @carolinesplate, or you can most likely find her out on the town on a Friday night.