Getting Around Town With Jamie Shupak: Valentine's Day Dos and Don'ts

Before you doing anything rash, consult this.

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Five days ago, I imagine your woman sat through the Super Bowl with you. Five days from now, you have a chance to show her how much you appreciate that—and the countless other reasons why you love her.

Um, hello? McFly? It’s Valentine’s Day.

Whether you think it the most romantic day of the year or just another Hallmark holiday is irrelevant come February 14th, because, by then, it will be an unavoidable topic—with your Mom, with co-workers at the water cooler, or with any woman you’re lucky enough to be dating.

Yes, I said lucky enough.

Mom says do this; your co-worker says do that; your guy friends say "do her." Here’s what I say: Dude, just do something.

But before you do, avoid some of the biggest Cupid-inspired blunders by consulting these dos and don'ts.

Don’t send her a dozen red roses if you’ve only been on a few dates. You do remember the too-much-too-soon guy who scared me off with that move, right? Roses are overdone and overpriced. Red roses are just plain aggressive.

Do send her a beautiful bouquet of some other type of colorful flower. If you have the access, ask one of her girlfriends which kind she prefers. And if you don't have the access, get it.

Don’t try to impress her by making a reservation at a ritzy restaurant where the prix fixe menu is double the normal price. You’ll wind up looking unoriginal and overeager, neither of which is good.

Do compile a menu of all her favorite foods and cook her dinner at home. Can’t cook? Order in from her favorite restaurant and set up an intimate table spread with flowers and a candle. (No, don’t use roses here either.)

Don’t shock her by showing up at her office or by sending some embarrassing singing telegram.

Do surprise her. Tell her what time you’re picking her up, but don’t tell her where you’re going. A woman likes a little mystery, but not a sneak attack at work.

Do acknowledge Valentine's Day with each of the women you’re dating—send a card or a gift or a sweet text. It’s not slimy if they’re all casual relationships. A guy has to keep his options open. 

Don’t admit to the women that you're keeping your options open.

Don’t be cliché and buy her lingerie. (Get that for her anyway, just on another day.)

Do something creative and plan a date that’s outside the box. The guy I’m dating scored tickets for us to see "The Daily Show" on Valentine’s Day because he knows how much I love Jon Stewart. You can be Casanova without the cheese. (Bonus: It cost him nothing. No excuses, guys.)

Don’t buy the expensive, fancy wrapped chocolates or chalky Valentine’s Day candy hearts, unless those are her favorite.

Do find the candy in the supermarket checkout aisle that best represents your feelings for her, like Sweet Tarts or Reese’s Peanut Butter Cups. Then drop the cuteness on her: “Oh baby, you’re all hard chocolatey on the outside, but mushy gushy peanut butter on the inside.” I’m kidding! Sort of.

Don't drop too much cuteness all at once.

Do dole it out slowly, the way an M&M melts in the mouth.

Don’t rely on cards in the drug store to tell her how you feel.

Do find a creative way to express yourself. Write it on a cupcake, engrave it on a piece of jewelry, or print out a picture of the two of you and write a note on the back. (Old school!) Or make her a Spotify playlist. (New school!)

Don’t break up with her on Valentine’s Day. It’s like telling someone their baby isn’t cute—you just don’t do it.

Do wait a day, or two or three—OR SEVENTEEN—before cutting the cord.

Don’t contact your ex. Resist the urge to call, email, gchat, Facebook, tweet, or text an old flame. No good can come of this. And if the ex happens to contact you? Well, that’s why your phone has caller ID and an ignore button.

Do call some of your single guy friends and have them meet you at the bar. Maybe you’ll even happen upon a single lady there who’s looking to forget an old boyfriend of hers.

Don’t tell her you love her because it’s Valentine’s Day.

Do tell her you love her because it’s Tuesday, and you treat everyday like Valentine’s Day.

In two weeks: Wassup, bro?

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