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20 Best Places in Greater Boston to Break Up with Somebody

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You know, sometimes relationships are overrated. You have to compromise and you can't quite control your own destiny in the same way as you could have when you were the single captain of your solo ship. Overall, you know if a person is meant for you (and, if that is the case, get out of here and check out this map of love instead). Otherwise, if you're looking at the Valentine's Day aisle of chocolate and heart-shaped everything with a sneer, then this is probably your kind of map. As you're plotting the perfect way to punctuate the end of a relationship, consider these potential places in Boston to do the deed.


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1. Copley Place

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100 Huntington Avenue
Boston, MA 02116

The central waterfall is the perfect place to drown your tears.

2. Sonsie

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327 Newbury Street
Boston, MA 02115
(617) 351-2500
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The steady din and good-looking crowd provide the perfect backdrop for The Talk and The Aftermath. If you're up for it, scope out the most eligible bachelor or bachelorette in the room.

3. Boston Public Library

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700 Boylston Street
Boston, MA 02116
(617) 536-5400
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If you don't like scenes, and your soon-to-be-ex-significant-other is a rule follower, head to a place that forbids yelling.

4. Amtrak South Station

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Break up. Catch the next train out. Done.

5. Jillian's Boston

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145 Ipswich Street
Boston, MA 02215
(617) 437-0300
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Instead of a pool of tears, just focus on a good game of pool. And check out the scene of many partiers up for a good time.

6. Dunkin' Donuts

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Boston University, 530 Commonwealth Avenue
Boston, MA 02215
(617) 236-7673
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If you don't know exactly where the deed needs to be done, don't worry--there's one on most every corner. Head here for an uncomplicated break-up. Just the way you like it. Get a donut ready for that jolt of sugar to book it out of there.

7. Arnold Arboretum

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125 Arborway
Jamaica Plain, MA 02130
(617) 524-1718

What better way to heal thine heart than to wander with nature?

8. South Station Bus Terminal

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700 Atlantic Avenue
Boston, MA 02111

Break up, but not before you check the bus schedule for an approximate idea of when the conversation can end.

9. Boston Logan International Airport (BOS)

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Boston Logan International Airport, 1 Harborside Drive
Boston, MA 02128
(800) 235-6426
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This is a no-brainer. If one of you has a plane to catch, this is one of the best places to let the world whisk you away and out of each other's lives forever.

10. Trinity Church

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206 Clarendon St.
Boston, MA 02116

When you're about to have a deeply emotional moment, sometimes it's best to be in a place that nurtures soul searching. Regardless of your religious status, you can keep your head down in a private pew and enjoy the quiet.

11. Copley Square

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Boylston Street
Boston, MA 02130

This location is a perfect point of departure to head separate ways--to Newbury Street or the mall for retail therapy, to a salon or spa for a pick-me-up, to the library for quiet contemplation or down any random street to think.

12. The Hong Kong

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65 Chatham Street
Boston, MA 02109
(617) 227-2226
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After you split that final scorpion bowl, you can go dance with a crowd. Or, more importantly, make sure there's karaoke happening so that you can sing "I Will Survive."

13. Four Seasons Hotel Boston

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200 Boylston Street
Boston, MA 02116
(617) 338-4400

For a heart-to-heart, the lounge is a quiet place to do it with dignity.

14. The Liberty Hotel

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215 Charles Street
Boston, MA 02114
(617) 224-4000
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Why wouldn't you break up at a place that has such a poetically appropriate name? Free your heart!

15. Bond Restaurant & Lounge

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250 Franklin Street
Boston, MA 02110
(617) 451-1900
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There couldn't be a more sophisticated and beautiful place to break up.

16. Finale Desserterie & Bakery

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1 Columbus Avenue
Boston, MA 02116
(617) 423-3184
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Avoid a bitter ending and go to Finale where the final act can be potentially sweeter over a dessert.

17. Old State House

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206 Washington Street
Boston, MA 02109
(617) 720-1713

Make the end a historic one. This place helped with our country's freedom, and it can be the stage for yours, too.

18. Massachusetts State House

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1 Ashburton Place
Boston, MA 02108

Because you need to make it official that it's over, you're going to need the government to back you up.

19. Boston Common

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Tremont Street
Boston, MA 02108
(617) 635-4505
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This place is so expansive, you're bound to find a private spot where you can have a private conversation.

20. The Whiskey Priest

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150 Northern Avenue
Boston, MA 02210
(617) 426-8111
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For the tough break-ups, there is a litany of whiskey options to stiffen that upper lip.

1. Copley Place

100 Huntington Avenue, Boston, MA 02116

The central waterfall is the perfect place to drown your tears.

100 Huntington Avenue
Boston, MA 02116

2. Sonsie

327 Newbury Street, Boston, MA 02115

The steady din and good-looking crowd provide the perfect backdrop for The Talk and The Aftermath. If you're up for it, scope out the most eligible bachelor or bachelorette in the room.

327 Newbury Street
Boston, MA 02115

3. Boston Public Library

700 Boylston Street, Boston, MA 02116

If you don't like scenes, and your soon-to-be-ex-significant-other is a rule follower, head to a place that forbids yelling.

700 Boylston Street
Boston, MA 02116

4. Amtrak South Station

Boston, MA

Break up. Catch the next train out. Done.

5. Jillian's Boston

145 Ipswich Street, Boston, MA 02215

Instead of a pool of tears, just focus on a good game of pool. And check out the scene of many partiers up for a good time.

145 Ipswich Street
Boston, MA 02215

6. Dunkin' Donuts

Boston University, 530 Commonwealth Avenue, Boston, MA 02215

If you don't know exactly where the deed needs to be done, don't worry--there's one on most every corner. Head here for an uncomplicated break-up. Just the way you like it. Get a donut ready for that jolt of sugar to book it out of there.

Boston University, 530 Commonwealth Avenue
Boston, MA 02215

7. Arnold Arboretum

125 Arborway, Jamaica Plain, MA 02130

What better way to heal thine heart than to wander with nature?

125 Arborway
Jamaica Plain, MA 02130

8. South Station Bus Terminal

700 Atlantic Avenue, Boston, MA 02111

Break up, but not before you check the bus schedule for an approximate idea of when the conversation can end.

700 Atlantic Avenue
Boston, MA 02111

9. Boston Logan International Airport (BOS)

Boston Logan International Airport, 1 Harborside Drive, Boston, MA 02128

This is a no-brainer. If one of you has a plane to catch, this is one of the best places to let the world whisk you away and out of each other's lives forever.

Boston Logan International Airport, 1 Harborside Drive
Boston, MA 02128

10. Trinity Church

206 Clarendon St., Boston, MA 02116

When you're about to have a deeply emotional moment, sometimes it's best to be in a place that nurtures soul searching. Regardless of your religious status, you can keep your head down in a private pew and enjoy the quiet.

206 Clarendon St.
Boston, MA 02116

11. Copley Square

Boylston Street, Boston, MA 02130

This location is a perfect point of departure to head separate ways--to Newbury Street or the mall for retail therapy, to a salon or spa for a pick-me-up, to the library for quiet contemplation or down any random street to think.

Boylston Street
Boston, MA 02130

12. The Hong Kong

65 Chatham Street, Boston, MA 02109

After you split that final scorpion bowl, you can go dance with a crowd. Or, more importantly, make sure there's karaoke happening so that you can sing "I Will Survive."

65 Chatham Street
Boston, MA 02109

13. Four Seasons Hotel Boston

200 Boylston Street, Boston, MA 02116

For a heart-to-heart, the lounge is a quiet place to do it with dignity.

200 Boylston Street
Boston, MA 02116

14. The Liberty Hotel

215 Charles Street, Boston, MA 02114

Why wouldn't you break up at a place that has such a poetically appropriate name? Free your heart!

215 Charles Street
Boston, MA 02114

15. Bond Restaurant & Lounge

250 Franklin Street, Boston, MA 02110

There couldn't be a more sophisticated and beautiful place to break up.

250 Franklin Street
Boston, MA 02110

16. Finale Desserterie & Bakery

1 Columbus Avenue, Boston, MA 02116

Avoid a bitter ending and go to Finale where the final act can be potentially sweeter over a dessert.

1 Columbus Avenue
Boston, MA 02116

17. Old State House

206 Washington Street, Boston, MA 02109

Make the end a historic one. This place helped with our country's freedom, and it can be the stage for yours, too.

206 Washington Street
Boston, MA 02109

18. Massachusetts State House

1 Ashburton Place, Boston, MA 02108

Because you need to make it official that it's over, you're going to need the government to back you up.

1 Ashburton Place
Boston, MA 02108

19. Boston Common

Tremont Street, Boston, MA 02108

This place is so expansive, you're bound to find a private spot where you can have a private conversation.

Tremont Street
Boston, MA 02108

20. The Whiskey Priest

150 Northern Avenue, Boston, MA 02210

For the tough break-ups, there is a litany of whiskey options to stiffen that upper lip.

150 Northern Avenue
Boston, MA 02210