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Word: heartbreakingly (lookup in dictionary) (lookup stats)
Dates: during 1980-1989
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Usage:

...years ago, the Crimson Express was on its way to an 8-2 season and an undisputed Ivy League title. But its stop in Ithaca was nothing but a heartbreak. Leading 17-15 in the last two minutes of the game, the Crimson was forced to punt the ball away. A few plays later, wide receiver Shaun Hawkins played hot potato with the ball in the end zone before clutching the desperation pass for the dramatic, go-ahead touchdown...

Author: By Michael Stankiewicz, | Title: Gridders to Invade Ithaca | 10/14/1989 | See Source »

...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 »

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