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Word: heartbreaking (lookup in dictionary) (lookup stats)
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Usage:

...miss the Heartbreak of Fenway, otherwise known as the Boston Red Sox. Make reservations early, because tickets are scarce in September, although you sometimes may be able to get bleacher seats on the day of the game...

Author: By Michael Stankiewicz, | Title: Harvard, the Haven for Armchair Athletes | 7/7/1989 | See Source »

...wasn't for lack of trying. The heartbreak and frustration was evident on many faces. There just weren't any answers...

Author: By Jennifer M. Frey, | Title: Images of Celebration Hide Frustration | 6/8/1989 | See Source »

...KINISON: HAVE YOU SEEN ME LATELY? (Warner Bros.). Abusive, scurrilous and hilarious: post-punk comedy meets primal-scream therapy. Offensive? You betcha. But there are wonderful bits about sexism and heartbreak, as well as the best riffs on organized religion since Lenny Bruce...

Author: /time Magazine | Title: Critics' Choice: May 1, 1989 | 5/1/1989 | See Source »

...KINISON: HAVE YOU SEEN ME LATELY? (Warner Bros.). Abusive, scurrilous and hilarious: postpunk comedy meets primal-scream therapy. Offensive? You betcha. But there are wonderful bits about sexism and heartbreak, as well as the best riffs on organized religion since Lenny Bruce...

Author: /time Magazine | Title: Critics' Choice: Apr. 24, 1989 | 4/24/1989 | See Source »

...infamous Heartbreak Hill? For Goar, it was no heartbreak. No problem...

Author: By Julio R. Varela, | Title: The Memories of Some Harvard Runners | 4/18/1989 | See Source »

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