Dated for the first time: June 2006 - December 2007
Dated for the second time: May 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 got back together in May 2009, a few months after Nick's split from Selena Gomez and quickly after Miley's split from Justin Gaston. However, they broke up again by July 2009, and Miley quickly began dating Liam Hemsworth.