A Gentleman's Guide to Not Screwing Up Valentine's Day

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If you're reading this with shaking hands and a sweaty forehead, you must be one those guys worried about pissing off your girlfriends on Valentine's Day. We're not here to say that your anxiety is unjustified. Probably, it's completely warranted. A well-intentioned-but-still-wrong move can leave you with a grouchy, unmanageable woman, which could leave you booty-free on the day of love.

What's a clueless man on Valentine's Day to do? Listen very closely: Drop that box of Russell Stover candy and make your way through Complex's no-fail guide to winning cupid's favor: A Gentleman's Guide to Not Screwing Up Valentine's Day.

Play the numbers game

Play the numbers game

Slow down, Romeo. Before you unveil your master plan, think twice. Your Valentine's Day efforts will be examined closely, especially if you're in the early stages of the relationship. If you're not exclusive, and you leave no gesture unmade, you might be perceived as wanting to get more serious. This might frighten her, or give her false hope. Similarly, if you're already exclusive and you do too little, you look lazy, complacent. The statement is something like, "I know I have no chance of getting laid tonight."

Below, find an easy guide to deciphering just how much is expected of you based on how long you've been dating:



  • 2-5 months: the nicest dinner you can reasonably afford. A simple bouquet of flowers (not roses, they're pointlessly pricey and clichéd) and, if you see things going somewhere, a card.


  • 6-12 months: At this point, you're committed, so most women will have expectations. Some thoughtful, non-generic gesture would be appropriate. A card is definitely required (and please write something in it).


  • A year and beyond: Even if this is your fifth Valentine's Day together, you're still expected to put in significant effort, especially if you've been slacking lately. Take the time to show her why you're still dating. In your card, write something specific about why you still love her just as much as the first time you said it.


Don't wait.

Don't wait

Honestly, the second you finish reading this, you should be on OpenTable making dinner reservations (for whatever's left—you're already behind on this one), scrambling to the nearest chocolatier, and generally getting your ass in gear. If you think you're going to whip up something last minute and make it appear thoughtful, you're wrong. She will know.

Don't buy anything from the drugstore. Don't. It's not so much the lack of quality that gets you in trouble (though, yeah—that too), it's more the extreme lack of planning. Hypothetically, you could have just remembered it was Valentine's Day twenty minutes ago and dropped into the Duane Reade on the corner, wildly grabbing things from the shelves. There is nothing romantic about that.

The effort expended and the foresight behind it is everything.

Work with what you've got

Work with what you've got

Let this sink in: Valentine's Day is about demonstrating the depth of your feelings, not the depth of your wallet. If your romantic gesture is going to put you out for the next month, hold off. A woman worth keeping will respect you for not over-extending your bank account for a single calendar day.

Work within your means. Instead of doling out money you don't have, get creative. If you can't afford a fancy dinner, have her over for cheese and Prosecco (Italian sparkling wine that costs a fraction what Champagne does). Turn your living room into a love den with as many cheesy Valentine's Day-themed decorations you can find.

An ordinary night can be made memorable with minimal cash and out-of-the-box ideas. Can't afford Godiva? Make some homemade chocolate-covered strawberries. A hotel room for the night isn't in your budget? A bag of tea lights and Hershey's Kisses cost a few dollars, and can transform her bedroom into a swoon-worthy oasis. Fancy cards too pricey? Try scribbling a love letter on the back of a photo of the two of you, or on a love-oriented Tumblr image (search: Love) you printed off at Kinko's for a few cents. Can't swing jewelry? String together small pieces of folded paper with compliments on them that she can "wear" for weeks. You have options if you give yourself time to plan and execute.

Drop some knowledge on her

Drop some knowledge on her

Don't lecture her about where Cupid's arrow originated. We mean show this woman how well you know her. Artisanal chocolates are a great start, but getting macaroons because you know she loves coconut takes your sweet surprise into the clouds. If you bring a bottle of wine, great, but if it's a sauvignon blanc because that's what she always orders at dinner, you're winning.

Real romance comes from listening. Some women hate flowers and consider them a waste of money. If you've been listening, you should know that by now. If you bring her chocolates and she's lactose intolerant, you fucked up. She can tell when you've been listening.

Also, many women are guilty of hint-dropping. Not because she needs everything she mentions, but because she wants to help you. Please, listen to your girl! If she's casually mentioned 300 times that she loves cupcakes from Magnolia, bring her a damn cupcake!

Its not just the thought that counts. It's your thoughts.

Not just the thought, but your thought

Don't even think about getting her one of those cheesy cards that go on for paragraphs with cloying sentiment. Get a card that's blank inside (Papyrus has great ones) and break out the pen. Don't make sweeping statements, just write sincere sentences. See, that wasn't that hard, was it?

Get hands on

Get hands-on

We don't expect you to go into full-blown Martha Stewart mode and knit a scarf, but if you baked some heart-shaped cookies, your girl would be pretty damn impressed. Get dirty.

If you made your valentine from construction paper and smelly markers, or spelled out your message of love with Scrabble pieces, you've done well. Just don't take this approach with flowers. Yanking tulips from your neighbor's planter isn't hands-on, it's just wrong. There's a fine line here, gentlemen.

If you're in love. Like, really in love, put everything on the table

If you're in love, lay your cards out

This is not for unrequited love. This is for full-blown, we're-in-this-together, you-are-the-one type ish. Go full force with everything you've got. Be daring, a little ridiculous—don't be afraid to look foolish.

Let your heart lead you around town. Get inspired. Go all in and commit to the idea, whatever it is. Do everything in the world to make this woman—your woman—know how much you love her. No matter how little you spend, or how cheesy it gets, she'll hear you loud and clear.

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