The 10 Worst Engagement Proposal Ideas


At our age, you quickly realize that more and more people you know are getting married. As even the girl with the unfortunate reputation in college, who has gained 30 pounds since then, ties the knot with the unemployed guy who makes money selling weed to high schoolers, you realize that these engaged and married folk are no longer out of the ordinary.

By browsing all of the people “in a relationship” on Facebook, you additionally catch a torrent of ugly jewelry and awful engagement videos. Since I’m dating a girl who talked about marriage numerous times before we even got together, I also get to hear about them on top of it. Like any good boyfriend, I originally decided to mess with her by creating absurd engagement scenarios, but I discovered that truth is unfortunately stranger than fiction. As she told me actual proposal stories of people she knew, hopefully not very well, I was left both dumbfounded and horrified.

The following methods are fantastic ways to embarrass yourself with the person you at least originally intend to spend forever with and sadly enough, most of them have actually happened. Since I’m a guy, there’s a chance I’m missing something about how “omg adorable” these situations would be, so feel free to let me know in the comments.

1. Flash Mobs


While the shock and awe approach works well for military engagements, people who think that a choreographed, dance-infused, public bombardment would be appropriate for an incredibly personal occasion are probably the same people who apply to be on reality TV shows. All a flash mob shows is that you are capable of putting a lot of time and effort into something that is completely unnecessary.

2. Sporting Events


Similarly, don’t put the girl on the spot when she’s surrounded by tens of thousands of strangers. If she really doesn’t want to marry you, she’s either going to embarrass your dumb ass in front of everyone or accept for the crowd and then dump you a month later. It’s a ballsy move, I’ll give you that, but it’s a tacky one. Go seek attention elsewhere.

3. Valentine’s Day


“But, Roger, it’s such a romantic day!” No, it’s a cop out. If you need an entire industry to manufacture romance for you instead of doing it yourself, you’re a lost cause. You’re also a dick for trying to show up every other guy at the restaurant. “Oh, you got your girlfriend flowers, chocolate, and dinner? I got mine a diamond ring, sucker!” Asshole.

4. Right After Sex


Might as well play up actual romance then, right? If you’re one of those guys who plans on pulling the ring from under the pillow after you pull out, you need to re-examine your thought process. You aren’t in some 98 degrees video here and your girl doesn’t want to take pictures of her ring on the same hand she just wiped her stomach off with. Be a little more considerate here.

5. With The Family


She’s going to be a part of your family and you’re going to be a part of her family soon enough. Might as well do it while with one of the above, right? Wrong. Proposing at a family dinner, on a family vacation, or during a family holiday is nothing but awkward. If she says no, you’re either stuck with them or she’s either stuck with yours. You both are going to have to deal with in-laws constantly in your business soon enough. Don’t let them ruin something else.

6. In Your Pajamas


Tons of girls like Twilight. Somehow, the thought of a man standing silently over you and watching you sleep is romantic to some people. Since you aren’t a vampire, maybe you want to throw rocks at her window or play the guitar outside of it to wake her up because you’ve seen it in a movie. Nope, still a bad idea. Your girl, being a girl, will want tons of pictures of this occasion, and she doesn’t want them to be of her in a robe, with pore strips on, a retainer in her mouth, and her eyes half open. Like her parents, you’re going to have to deal with that image soon enough too.

7. Via Scavenger Hunt


Maybe you think just getting down on one knee and asking her is boring or not adventurous enough, so you think sending her throughout a city or to the bottom of a lake makes the process that much more fun. A proposal shouldn’t be a chore, however, so you should just cut the act. There are so many things that could go wrong throughout this process, such as a homeless guy stealing one of the notes or the ring getting lost in sand and mud in the water. Keep that expensive thing with you and don’t let go of it until the end.

8. In A Food Or Beverage

engagement ring cake 2_enl

Speaking of losing it and situations that can go horribly wrong, putting the ring in food or at the bottom of a glass can be far too risky as well. She could choke on it, or worse, swallow it whole, effectively tearing her GI tract to shreds and then you’re back to square one with a dead girlfriend. Best case scenario, that’s a lot of money to have pass through your girlfriend’s bowels and I doubt she’s going to put it right on her finger after you fish it out of the toilet. At dinner is a fantastic idea. In dinner is just asking for trouble.

9. By Being Cheap


Taco Bell apparently has hot sauce packets that say “Will you marry me?” Nothing says true love like fast food condiments, amirite? While they certainly are free, you’re also cheap as hell. This is as bad as giving her an empty ring box and telling her that you’ll fill it one day but even cornier. Marriage is a financial commitment as much as it is a personal one, and if you can’t afford to at least buy a ring, much less a nice one, you probably should be focused on other things at the moment. There is a difference between financial responsibility and sheer laziness.

10. Banners


The absolute worst is when you don’t even have the balls to actually ask her with words from your mouth. If an airplane banner, scoreboard, text message, or Facebook post asks her to marry you, you are an unbelievable wimp. “Will you marry me?” is a four word sentence, and if you can’t muster up the courage to spit it out, instead content to simply smile and point, chances are you’re not ready for marriage in the first place.

The catch of course to all of these is that if you know that’s what she’s looking for, you should do it anyhow. The point, after all, is to make her happy. I would judge you for dating someone who isn’t quite right in the head in the first place, but I’m not about to throw rocks from my glass house. Still, proposals and engagements are deeply personal events and should be treated with the intimacy they deserve. Perhaps if more people considered what they were doing instead of thinking of an extravagant way to do it, engagements and marriage would have a higher success rate.

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I used to write for TFM and PGP when they were funny.

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