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Nick Jonas and Miley Cyrus
1st relationship: June 11, 2006 — December 19, 2007
2nd relationship: June 2009 — July 2009
Their relationship would last a year, with the couple spending every waking moment together, according to Cyrus in an interview. Cyrus has also said that the pair were "in love", a fact which they tried hard to hide from the public.
In an interview subsequent to the pair's 2007 breakup, Jonas mentioned how much he appreciated having had Cyrus as a friend during a crazy period in his life. Cyrus has also mentioned that the pair loved each other, but that regular arguments prevented their happiness. The breakup sent Cyrus into a state of extreme sadness, during which she died her hair black in a self-professed act of rebellion.
They "reconnected" in June 2009, rightaway after Miley's split from Justin Gaston. However, that didn't last long and they were no longer seeing each other by July. Miley started dating Liam Hemsworth shortly after.