Worst Proposal Ever: A Psycho’s Guide To Popping The Question

Author Lauren Beckham Falcone

August 12th 11:23 AM

To give a wholesome proposal
byu/stevemw intherewasanattempt

Worst Proposal Ever.

Hands down.

So, you think you’ve seen it all? Think again. Buckle up, because I’m about to tell you about the worst, most psycho marriage proposal ever.

Ready?

Picture this: You’re in Russia (because where else would this happen?), minding your own business, maybe thinking about what to have for dinner, and then bam—a van screeches to a halt in front of you.

Out jump a bunch of ski-masked thugs, and before you know it, they’re dragging your boyfriend out of the car.

They start beating him with tire irons, and you’re standing there thinking, “This is it. This is how I become single.”

But wait! It gets worse. Just when you’re about to dial 911—or whatever the emergency number is in Russia—your boyfriend jumps out of the van, not beaten to a pulp but holding… wait for it… a bouquet of flowers and an engagement ring.

Cue dramatic music.

Yep, he just faked his own kidnapping to propose to you. Because nothing says “I want to spend the rest of my life with you” like orchestrating your own fake murder. The girlfriend? She was terrified, obviously, but somehow she still said yes. I guess the fear-induced adrenaline rush worked in his favor.

Now, let’s be clear.

This is not how you propose.

This is the opposite of how you propose. In fact, if you’re even thinking of something this crazy, just stop. Take a deep breath, and consider therapy—because you might be a psycho.

Instead, why not go for something a little more… sane? Like hiding the ring in a box of chocolates, proposing at a favorite spot, or using your dog as the ring bearer. Heck, even proposing with a cheesy line like, “Will you make me the happiest person alive?” is better than a mock abduction.

So, let’s all agree to keep the tire irons out of our proposals, okay?

Because, honestly, no one should have to say “I do” with their heart still racing from fear.

Lauren Beckham Falcone is the co-host of Bob & LBF in the Morning. Formerly an award-winning reporter and columnist for the Boston Herald, she credits her current success as a pop culture commentator to watching too much TV as a kid and scouring the internet too much as an adult. LBF is a regular contributor to NECN and is an honorary board member at the Massachusetts Down Syndrome Congress. Lauren lives in Canton with her husband Dave and her daughter Lucy. Lauren writes about trending topics, New England destinations, and seasonal DIY.

Whatever You Do, DON'T Propose At These 9 Boston Locations

Don’t propose at these Boston locations!!!!!! Sorry, I feel like I’m yelling, I didn’t mean to do that.

Love is a beautiful thing. But let’s face it, proposing marriage is a make-or-break moment. You’ve found the perfect partner, but now it’s time to find the perfect place to pop the question. While Boston and the New England area are full of romantic spots, there are a few locations you should avoid like a seagull aiming for your picnic. Buckle up and get ready for a hilariously cautionary list of the worst places to propose.

On the other hand, if you’re looking for a nice place to propose in Boston or the New England Area I suggest places like The Boston Common, Menemsha Hills (where I got engaged!), the White Mountains in NH, Acorn Street near the Boston Common, or even at home in private over a nice candle-lit dinner.

By the way, this is just for fun. Remember, proposing is all about creating a moment that will be cherished forever. While these places in Boston might provide a good laugh, it’s best to choose a location that truly reflects your love and ensures a romantic, rather than comedic, outcome.

The Worst Places In Boston To Propose (Drumroll Please…)

9. Fenway Park
(Photo by Jim McIsaac/Getty Images)

Picture this: You’ve planned a romantic evening at the iconic Fenway Park, home of the Boston Red Sox. The atmosphere is electric, and you’ve got your heartfelt speech ready. But wait, is that a home run flying straight towards your intended? Yup, bad timing strikes as the ball smacks into their face, leaving your proposal in a foul state. Lesson learned: Leave baseball to the professionals and propose elsewhere.
8. Salem Witch Trials Memorial

While history can be intriguing, it might not be the ideal backdrop for a moment of eternal love. Imagine dropping down on one knee beside a memorial honoring the victims of the Salem Witch Trials, only to be interrupted by a group of modern-day witches having a cackling contest nearby. Talk about a spell gone wrong!
7. The Big Dig Construction Zone, Or ANY Zone For That Matter

In a city famous for its never-ending construction projects, proposing in the middle of a Big Dig construction zone is a recipe for disaster. As you reach for the ring, a rogue backhoe starts digging up the ground beneath your feet, leaving you and your sweetheart running for cover. It’s hard to convey love when you’re wearing a construction helmet.
6. Nantucket's Foggy Cliffs

Nantucket’s cliffs offer breathtaking views, but proposing there is like playing hide-and-seek with destiny. The dense fog rolls in at the most inopportune moment, obscuring your heartfelt words and transforming your romantic gesture into a spooky mystery novel. You might end up proposing to a startled seagull instead!
5. The Boston Tea Party Ships & Museum

While historical reenactments can be entertaining, they rarely set the stage for a smooth proposal. As you’re about to ask for your partner’s hand, a faux British soldier bursts in, shouting about taxation without representation, and accidentally knocks you into a crate of “tea” (actually just water). It’s hard to top a soggy proposal, and the only thing brewing is embarrassment.
4. The T

Nothing says “romance” like proposing in a crowded train car, sandwiched between a guy with smelly armpits and someone munching on a tuna sandwich. It’s a surefire way to derail your proposal plans.
3. A Duck Boat

Imagine trying to profess your undying love while quacking like a duck and splashing into the Charles River. Trust us, your partner won’t be the only one quacking up with laughter.
2. The Make Way for Ducklings Statue

While the bronze ducklings are cute, they don’t exactly set the mood for a proposal. Plus, you might find yourself competing for attention with children climbing all over the statue, leaving you feeling like a third wheel to a bunch of ducklings.
1. The "Cheers" Bar

Everybody may know your name, but proposing at the Cheers Bar might make your partner think you’re just after a never-ending happy hour. Skip the sitcom-inspired proposal and aim for a more unique and memorable venue.