While it's not clear when Leo and Orlando first met, the two have been snapped together at industry parties and environmental events, including Leo's annual foundation gala in St-Tropez, since 2005. In 2014, the two were tangled up in a weird web of celebrity relationship drama during a trip to Ibiza involving Justin Bieber, Lindsay Lohan, and Orlando's ex-wife, Miranda Kerr. Justin reportedly said something offensive to Orlando (possibly concerning him hooking up with Miranda while they were still married), which sparked the pair's scuffle; Orlando was caught on tape slapping the singer in the head while Leo and Lindsay were seen clapping and laughing as it happened. Most recently, Leo helped Orlando shake off his breakup with Katy Perry by partying together at Coachella.
