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Valentine’s Day Proposal Ideas

Posted by Kyle Design on February 2, 2012

If all goes right, when the newly engaged woman gets asked that inevitable “Did you see it coming?” question, she’ll answer “No” and she won’t be lying. If you’re married (or recently engaged), think back to the day IT happened and be honest…did you know? When my husband proposed on a romantic horse-carriage ride through downtown San Antonio, I definitely saw it coming, as did my best friend when her fiance popped the question overlooking the San Francisco Bay. But my step-mom was caught by surprise when my dad pulled out a ring during a scenic motorcycle ride in Maui, my cousin wasn’t expecting it when she got engaged on a theater stage in front of an audience of a thousand during her cruise vacation, and my sister-in-law didn’t see it coming when she left with my brother for a Valentine’s dinner and movie date.

…That’s one way for a guy to kill 2 birds with 1 stone – propose on Valentine’s Day. He’s got the V-day gift covered and he doesn’t have to create another romantic experience down the road – score! (My brother took it a step further and got married on Valentine’s Day – a guaranteed way to never forget his anniversary.)

Once a guy decides V-day is THE day, he’s gotta figure out how to pull it off – especially if she might be expecting it. So what are some sneaky ways to propose on Valentine’s Day? It’s a little tricky since the romantic holiday falls on a weekday this year, but there’s still plenty of great ways to pull it off…

She couldn’t say “no” to this!

♥ Get her a puppy or kitten, get a heart-shaped pet tag and engrave “Marry Me” on it, then place the tag and the ring on the collar, and wait for her to find it.

♥ Take her to a romantic dinner where she might expect the proposal, but surprise her later by going to a movie where you’ve paid to have a message appear on the big screen before the movie starts. While she’s reading it, pull out the ring.

♥ Get her a box of chocolates but open it before you give it to her and replace one of the chocolates with the ring. Bonus points if the chocolates are her favorite pick (not the variety box) from a yummy high-end shop like See’s Candies. (Trust me, for my 30th birthday my boyfriend got me a box of 30 Dark Chocolate Butter truffles from See’s and I’m pretty sure that’s when I knew he was The One. Check out their easy-to-order custom boxes.)

♥ If you want to propose over dinner, talk to the restaurant beforehand and see if they can do something special like write “Marry Me” in chocolate sauce on her dessert plate or place the ring box among other desserts on the dessert tray. Consider buying an engraved ring box from Kyle Design to mark the occasion. You can engrave “Will you marry me?” plus her name and the date.

Proposal Fortune Cookie from

Recreate your first date or somehow incorporate your first date into the night – for example, if you ate Chinese food on your first date propose with a personalized fortune cookie message or if you went ice skating, propose on the rink or buy her a pair of ice skates and tie the ring on the laces or engrave “Will you marry me?” onto the blades (yes, that can be done!).

♥ Just when she thought it wasn’t going to happen – use glow-in-the-dark star stickers to spell out your proposal on the ceiling above your bed. At bedtime, climb in, turn out the lights, and wait for her to gasp in excitement.

Get a personalized gift from Kyle Design (like a custom purse pill box, heart purse hook, or heart business card case) and engrave “Will you marry me?” on it. At first she’ll just think you got her a thoughtful gift, but when she reads the proposal she’ll get the real gift, at which point you can pull out the ring. (We like the business card case because she can use to it hold wedding vendor business cards while she plans the wedding!)

Silver Heart Business Card Holder for Women

Engraved Heart Business Card Case for Wedding Planning

Custom heart engagement ring box

Valentine's Heart Handbag Holder

Engraved Heart Purse Holder V-day Gift for Women

If you know someone who’s going to propose this Valentine’s Day, pass along some of these creative proposal ideas. And tell him to make it even more special with an engraved heart ring box from Kyle Design.


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