Sure there’s upside. If you propose to the girl on Valentine’s Day, you kill two birds with one stone, you stretch your flower budget, and you will never forget the date of your engagement. It’s also true that approximately 35% of women will consider this addooooorrrable. 4% of men will approve, and 0% of your buddies will think it’s in good taste. As for the only constituency that truly matters, your girlfriend? Tougher call. It’s not that she will hate the proposal. Maybe she’s a Hallmark Girl and she’ll think it’s sweeter than cotton candy dipped in honey, topped with chocolate sprinkles.
Yet there are risks. Such as… For many people, cotton candy dipped in honey, topped with chocolate sprinkles will taste like ass. Unless you have unshakable proof that your girlfriend really, reeeaaaly craves a Valentine’s Day Proposal, don’t do it for these 5 reasons:
You’re Forcing Her to Share
If you propose to her on October 10th, I guarantee that she won’t get lost in all of the other Columbus Day Proposals. The weekend will belong to her and her alone. If you propose on V-Day? She’s forced to share. This isn’t just her day, it’s everyone’s romantic day, thus diluting the sanctity (and singularity) of the moment. Yes, you are killing two birds with one stone… and that might not be lost on her. Take your time killing the birds, kill the two birds on two different days, make the death linger and make it your own.
You Will Make Every Other Guy Feel Like a Dick
Imagine that you’re at a glitzy restaurant. Valentine’s Day. She’s in a dress, you’re looking as un-slob-like as you possibly can, and you’ve even put on deodorant. It’s romantic as shit. Now imagine that you slip the maître d’ some twenties, wave over the violinist, get on one knee, and present her the diamond ring. Every other dude in that room will hate you. On this most fragile of days–a holiday that tests and strains relationships–you just injected sinister ideas into their own girlfriends’ heads.
Proposing on Valentine’s Day is well past cheesy. It’s milky. It’s even more watered down and it goes bad faster. Do you really want this to be your first move as her soon-to-be husband? Is this the way you want to define your marriage, your family, the rest of your life?
She Might Vomit on the Ring
The above reason–milkiness–is just a theoretical reason. Abstract. It’s wrong for philosophical reasons, but it might not have any practical consequence. (Like not voting, say.) The chances are high, however, that there will be consequences. She might find it corny, she might be embarrassed. Not every girl will feel this way. But some will. Why take the chance? What’s the upside?
You’re Getting an Emotional Tattoo
You can never undo this. Never. And she will tell the proposal story again and again and again. So, if you cheese it up and propose on Valentine’s Day, you won’t just be lame on February 14th, you’ll be lame every time she retells this story, for now, for your engagement, for your wedding, and for every day until you die your cheesy death.