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

    Fenway Park most expensive MLB park

    (Photo by Jim McIsaac/Getty Images)

    skyview of fenway park at night
    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

    witch with green face and long nose

    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

    big dig
    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

    man and woman on a foggy cliff
    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

    tall ships in Boston
    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

    Boston T station, Park Street
    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

    multiple duck boats lined up in Boston
    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

    Warm Weather Arrives In Boston. 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

    man standing in front of 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.

Sign me up for the 105.7 WROR email newsletter!

Make sure you're in the know on the latest music and entertainment news, plus exclusive prizes, trips, and more!

By clicking "Subscribe" I agree to the website's terms of Service and Privacy Policy. I understand I can unsubscribe at any time.