For many, Valentine's Day, the national holiday of love, seems like the perfect time to propose. The day's already reserved, the anticipation is already building... Then again, there is an implicit pressure in trying to combine to momentous romantic occasions into one. The key is to let the natural romantic ambiance of Valentine's day work in your favor, while adding some unique touches to create a personal proposal.

The first thing to do, since you've already selected a traditional date to propose, is to avoid any traditional sweet-but-cheesy proposals. So, no chocolate script on the restaurant dessert plate, no skywriters, and no fortune cookies! Groomstand's unbeatable Valentine's Day Proposal Guide will get you from bended knee to "will you marry me?" with superb creativity and aplomb. Simply take one of our suggestions, wait for the ecstatic "Yes!" and then come back later to pick out groomsmen gifts!


Secretly type up a Valentine's Day Trivia Quiz. Start with general questions (i.e. "Is Valentine's Day a pagan or religious holiday") but make sure they are all yes or no questions. Have the last question be, "Will you marry me?"

HOW TO PULL IT OFF: Tell your lady you're exhausted from work and you just want to have a low-key night in. If she's a worth it woman, she'll be dissapointed, but agree. Get her to sit down next to you on the couch, then casually pull out a Valentine's Day trivia quiz you've typed up in advance. Pull it out of the newspaper and pretend it was an ad. Say, "Hey honey, I know you're bummed about spending Valentine's day in. I'm just going to jump in the shower, but why don't you take this Valentine's Day quiz to get in the spirit of things?" While she's taking a quiz, rush into the other room, where you will have stored the ring, flowers, and wine (bonus points for presenting it in our romantic personalized wine box - hey, it works for more than just groomsmen gifts). When you hear the tell-tale scream, rush back in the room, get on one knee, and propose.


Okay, I know we said no skywriters, but that's because we have a better idea. Have a star named after your intended, only with her first name and your last name (or your last names hyphenated, if you prefer.)

HOW TO PULL IT OFF: Take her to a scenic vista with plenty of star-gazing spots. Give her the document to open, then say "I want to spend the rest of my life star-gazing with you. Will you marry me?" Spend the rest of the night picking out "your" star. (For liquid courage along the way, just pack our travelin' flask)


We know it's not macho, but women do stuff like this all the time. Drop in on your local craft circle and get some knitting tips. Embroider "Will You Marry Me?" on a table cloth. Bonus points for multiple languages.

HOW TO PULL IT OFF: Invite her to an intimate dinner for two at home. When she gets up to go to the bathroom, switch your old everyday table cloth for your handcrafted masterpiece. Wait and see how long it takes her to notice. When she does, pull off dinner plate cover to reveal ring box. Say, "Honey, now you know that when I said I'd do anything for you, I really meant anything. Will you marry me?" If this feels too out of character, begin by using our men's manicure set to slowly get in touch with your metrosexual side. You'll be swapping crochet tips in no time, and you might even like the feeling enough to pass those out as groomsmen gifts!


If you two are sailing sweethearts, a romantic moonlight sail is your perfect Valentine's Day proposal.

HOW TO PULL IT OFF: Wait until the moonlight is just right, then tell her you have a Valentine's Day present for her. Give her this beautiful silver compass and tell her "With you, I can never lose my way. Will you marry me?" Have the compass engraved with a special message for a perfect proposal memento. Bonus points if she wears it on the wedding day.

NOTE: If you don't sail, another idea is to take her on a drive and pretend to get really lost. At the last moment, pull into a romantic spot, give her the compass and say, "I'm never lost as long as I'm with you. Will you marry me?"


Make the location of your Valentine's Day Proposal a huge surprise! Take her to a tropical butterfly museum for an exotic proposal she'll love re-telling.

HOW TO PULL IT OFF: Get on one knee and say "Honey, you've given me butterflies since the moment I met you. This is my chance to give some butterflies back to you. Will you marry me?"


Especially if you have been high school sweethearts or together for a long time, this Valentine's Day proposal is a sweet gesture. Plan a kid-themed day of amusement, ending with a timeless proposal. Spend a day swinging on swings, picking apples at an orchard, wading in a creek, and flying kites. At the end of the day, surprise her with either a grade-school style valentine that says "Will you Marry Me?" or even more classic, a simple folded "Will you Marry me? Check Yes or No" note.