Whether you’re dumping someone or you have a bad feeling you’re about to be dumped, picking a strategic location for that final, devastating conversation is key. Don’t add another layer of awkward on top of your misery-fest by meeting your significant other (soon to be ex-SO) at either of your apartments. No one wants to initiate the end of a break-up conversation by asking for a glass of water or to use the other person’s bathroom before taking off.
Keep it in a public place, allow yourself an escape route, and have comforting distractions nearby for that immediate fallout period. Boston has a few great places to stage a break-up:
If You’re a Crier |
No restaurants with servers, dude! There’s nothing worse than leaning over a little table to stage-whisper through your teeth at your girlfriend, only to straighten up and wipe your eyes when your server asks how you’re enjoying your crepes. Plus, a break-up in a restaurant is a landmine covered up with the idea of a potential date, so don’t let your significant other show up thinking they’re about to be wined and dined. That’s cruel.
For a quiet, tucked away table to do your worst, check out L.A. Burdick near Back Bay. It’s softly lit, but not in a romantic way. In fact, the chocolatier cafe feels a lot like your mother’s kitchen. Once your newly-minted ex leaves, this tiny chocolatier haus becomes a faux-European comfort womb. The women behind the counter are always kind, the baked goods are unbelievable, and you can drown your misery in the hot beverages they call “drinking chocolates,” which are so thick and buttery they’ll make you forget how cute she looked when she was angry.
For a quiet, tucked away table to do your worst, check out L.A. Burdick near Back Bay. It’s softly lit, but not in a romantic way. In fact, the chocolatier cafe feels a lot like your mother’s kitchen. Once your newly-minted ex leaves, this tiny chocolatier haus becomes a faux-European comfort womb. The women behind the counter are always kind, the baked goods are unbelievable, and you can drown your misery in the hot beverages they call “drinking chocolates,” which are so thick and buttery they’ll make you forget how cute she looked when she was angry.

If You Need to Find Zen |
Pro tip: running water is calming, and there’s a gorgeous waterfall in the middle of the mall at Copley Place. If you’re near the Pru and your boyfriend says something like “listen, we need to talk,” gather up your shopping bags and the dwindling remains of your pride and guide him toward this man-made aquatic masterpiece. Also, get the hell away from Copley Square, or “The Official Fanciest Wedding Photo Op in Boston”. You’re about to get your feelings stamped out like ants. You don’t need to see that stuff right now.
Once inside Copley Place, you can watch the waterfall while your boyfriend uses his best approximation of human decency to let you down easy. After he leaves, you can meditate as the running stream hits the pond at the bottom and travels back up again in some unknown, sturdy pipe. There’s probably a metaphor in there somewhere.
If you’re lucky enough to be fabulously wealthy, you can buy yourself a break-up bra at Intimacy down the south corridor. If you’re broke, you and your old, banged up trash bra can sit in the intense massage chairs without too much fuss and salesmanship from the staff. Bonus points if you’re crying.
Once inside Copley Place, you can watch the waterfall while your boyfriend uses his best approximation of human decency to let you down easy. After he leaves, you can meditate as the running stream hits the pond at the bottom and travels back up again in some unknown, sturdy pipe. There’s probably a metaphor in there somewhere.
If you’re lucky enough to be fabulously wealthy, you can buy yourself a break-up bra at Intimacy down the south corridor. If you’re broke, you and your old, banged up trash bra can sit in the intense massage chairs without too much fuss and salesmanship from the staff. Bonus points if you’re crying.

If You’re Claustrophobic |
Boston Common is actually a pretty good place to have a meltdown. There’s always an ice cream truck waiting on Boylston once you’re finished; just make sure your ex gets a cone and walks away before you make your approach. There’s also a lot to look at on the Common, in case you don’t want to stare into your boyfriend’s watery cartoon eyes while you stab him in the heart. You can always focus on the street performers, or the teen couples smoking weed on the bridge, or that balloon animal guy, or the kids on heelies. Visit the duck statues and remind yourself of what made you happy when you were a kid, before you decided you needed to make out with somebody.
If you’re allergic to grass or you don’t want to dump your boyfriend while Shakespeare on the Common actors traipse around in the background, Government Center can double as a wide-open heartbreak arena. Remember: the gross, 1970s-architecture and cement surroundings represent how hard and grey your soul needs to be. He didn’t treat you well, so close your heart up for business like the T stop!
If you’re allergic to grass or you don’t want to dump your boyfriend while Shakespeare on the Common actors traipse around in the background, Government Center can double as a wide-open heartbreak arena. Remember: the gross, 1970s-architecture and cement surroundings represent how hard and grey your soul needs to be. He didn’t treat you well, so close your heart up for business like the T stop!

If You’re Nervous |
The walk from the South End into Cambridge via Mass Ave is the perfect length for a heavy discussion, and at any point you can split ways, citing something interesting located a block to the left or right of where your new ex is standing. If you time it right, you can start laying down the hammer as you walk past Back Bay station, get into the gritty emotion-wielding whilst over the Charles, and be ready to “give them space” around MIT. If all else fails, you always yell “oh my god, what’s wrong with the CITGO sign?” and run when they turn toward the horizon.

Just don’t, Bostonians, don’t ever, for the love of god, break up with someone on the T. We’ve got enough people in tears on there as it is.