love & romance

10 conversations to have on the Brooklyn Bridge

Last weekend my boyfriend and I decided to walk the Brooklyn Bridge into Manhattan. We had already spent a few hours together that afternoon, drooling over the sofas we couldn’t afford in West Elm and drinking coffees side by side on a bench, scrolling through our Instagram feeds. As we started to walk across the bridge though, I became acutely aware that we were being somewhat forced into a conversation that required a level of concentration I usually reserve for writing these articles or (previous) first dates. We couldn’t glance at our phones or even really pause to admire the view, such was the intense flow of foot traffic. It was the first time all day that we really had each other’s undivided attention. Never one to miss an opportunity, I suggested that we do the “36 Questions.” For those of you who might be unaware, the 36 questions is a scientific study that turned into a viral Modern Love article for The New York Times. The claim is that by asking a potential love interest the 36 questions listed in the article, you will fall in love, due to the vulnerability the premise fosters.

It took us about half an hour to make it across the bridge and finish the questions, by which point we had cried together, laughed together and attempted a kiss that received jeers from a bunch of teenagers. (Is anyone else terrified of teenagers or is it just me?) “We should do that again some time” my boyfriend commented. It occurred to me that walking the Brooklyn Bridge offers a unique opportunity. This timeless New York pastime allows us twenty to thirty minutes of pure, unadulterated, old fashioned conversation to enjoy with a friend, lover, collaborator, family member or even stranger.

If you are anything like me, you will have noticed that your attention span has waned in recent years due to the invasion of social media. Having an intense discussion in public with no guidelines can seem daunting. So to help you out, I have created a list of conversations that you can have as you walk the Brooklyn Bridge.

Photo via Colton Duke/Unsplash


1. The 36 questions (obviously)

The questions are broken up into three sets, with each new section becoming progressively more personal. Sample questions include: “If you could change anything about the way you were raised, what would it be?” and “What is the greatest accomplishment of your life?” Try it out and please invite me to the wedding.

2. Make a plan

This can be done with a friend or alone. If you are about to embark on a project, chances are that your mind is reeling with all the ideas and possibilities. Take this time to formulate a plan or figure out the first step. By the time you reach Manhattan you’ll be dying to get back to your laptop in Brooklyn! (Perhaps it might be best to walk from Manhattan to Brooklyn for this scenario!)

3. Would you rather?

Not everything has to be serious (says the sarcastic Brit), why not partake in an epic game of “would you rather?” with a friend or a lover. You’ll laugh and probably learn something about each other too. Here are some starter questions: Would you rather be able to fly or be completely invisible? Would you rather have a head the size of a tennis ball or a head the size of a watermelon? Would you rather give or receive a lap dance?



Photo via Vita Vilcina/Unsplash


4. Make a gratitude list

I find this incredibly hard to do, but people swear by them. It’s all about shifting your perception. Even if you are a complete novice at this, take a look around you. You live in one of the most vibrant cities in the world, you are young enough and (hopefully) healthy, anything is possible. You can walk across a bridge! There is plenty to be grateful for. See how many things you can add to the list. You may be surprised by how #blessed you really are.

5. Mentor walk

If you are lucky enough to have a mentor in your life, you know how amazing they can be in guiding your career or your personal development. Why not take a walk with them across the bridge and ask them for advice on whatever issues you have been struggling with. Maybe just listen to them tell their own story of how they made it to where they are. Every day’s a school day – get learning!

6. Desert Island Discs

Desert Island Discs is a British radio show that has been on air since 1942 and is now a weekly podcast with an archive going back to the 50’s. The basic premise is that each guest is asked to bring along eight discs (songs) that they would take with them to a desert island. They explain their choices by contextualizing them within events from their lives. The first record they owned, or the song that played at their wedding, for example. Make your desert island playlist and share it with your lover or friend and explain what each song means to you. Perhaps when you reach Manhattan you can turn around and return, listening to their playlist and hearing their memories. For extra credit, you also need to pick a luxury and a book to take, just like they do on the radio show.

7. Riddles

My boyfriend and I were stuck on a packed train that wasn’t moving last week, so I called up some riddles on my phone. He rolled his eyes at first, but twenty minutes in, he was hooked and was begging me to ask him another. An example riddle might be: You have a fox, a chicken and a sack of grain. You must cross a river with only one of them at a time. If you leave the fox with the chicken he will eat it; if you leave the chicken with the grain he will eat it. How can you get all three across safely? (Answers in the comments please.) Simply google some riddles and take turns asking each other.

8. Pregnancy decision

Whoa Ruthie, that got dark. Yep, it’s not all fun and games on the bridge. If you aren’t trying for a baby and you find yourself pregnant, you will be forced to make an extremely difficult decision that can impact your entire future. Whether you take your partner or go alone, a long walk can really help you gather your thoughts. You may not reach a decision before you reach Manhattan, but taking the time to really give it some thought can certainly help in the process.

9. Air some grievances

If it’s not one thing it’s your mother amirite? We all have issues, family members who annoy us, irritating coworkers, slow walkers, but lashing out rarely solves anything. Why not take this bridge walk to really air out those feelings. Have the imaginary conversations where you confront your enemies and leave triumphant, dream up fun ways to really put some know-it-all in their place, imagine confronting your roommate about their disgusting bathroom habits. Then take a breath and step onto the island of Manhattan knowing that you’ll never send the letters you just wrote in your head because you are a bigger and more evolved person than they are. Namaste.

10. Tinder date

Want an intense first date? Meet at the bridge and walk across together. Bonus points if you line up another date for the trip back.

There you have it. Lot’s of fun to be had AND it’s free! Note: Having a deep and meaningful with your partner as you walk over the bridge is fine, but please try refrain from breaking up with someone on there, you know, because you’re on an effing bridge!

This post has been updated, originally published in 2017.


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