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Brookline High School alumni

Conan O'Brien
Mike Wallace
Robert Kraft
Johnny Contardo
Grace Kelly
Michael Bluestein
Davey Holmes
John Hodgman
Theo Epstein
David Susskind
Joan Darling
Alan Rachins
Richard N. Goodwin
Michael Dukakis
Kitty Dukakis
Yasmin Siraj
Lenny Baker
Safra A. Catz
Raffi Freedman-Gurspan
Robert Kingston
Fred Newman
Hugh B Cave
Jeff Adrien
George Kenney

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Paulien Cornelisse and Chris BajemaBreakup - 30th Sep 2026by missepticeye

Lil' Wayne and Madi CannonEngagement - 29th Sep 2026by missepticeye

Paul 'Pauly D' DelVecchio and Nikki Hall (personality)Engagement - 27th Sep 2026by Redhot79

Nathan Osmond and Annalee LundellEngagement - 27th Sep 2026by missepticeye

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