Handler has been romantically linked to the US rapper and who better to gush to about your love life than the queen of fairytales - Swift.
It came up when the star talked about her new album, Speak Now, which sold an impressive 1,047,000 copies in its first week.
She said: 'They say anybody since 50 Cent in 2005, yeah.
'I'm a big fan of 50 Cent, I think you're a big fan of 50 Cent.'
Chelsea joked: 'I'm not familiar with his music.'
The Mine singer seemed to be a big fan herself.
She said: 'When we're on tour, we have all three girls - the backup singer, the fiddle player, and me in one room, and we all warm up to 50 Cent music, it would be surprising how many lyrics I know.'
Handler added: 'I'm surprised that you warmed up to 50 Cent because I have warmed up to 50 Cent.'