4. John Mayer
John Mayer is known to Hollywood for his soulful music, but also for being smoulderingly sexy and a total heartbreaker. Names in his little black book include Jennifer Love Hewitt, Jessica Simpson, Minka Kelly and Jennifer Aniston. In 2009 when John was 31 he had a quick one-month relationship with a 19-year-old Taylor Swift. The fling ended in Taylor writing that famous break-up song “Dear John”. In the lyrics, Taylor calls out John for messing with her at such a young age and playing “dark twisted games.” I wonder how many of John’s exes were praising “amen” to that one!
Following Taylor, John stayed off the dating radar and then in 2012 dated Katy Perry on and off for about a year. The two songbirds almost seemed like they were ready to tie the knot until breaking it off for good in 2014. I guess getting too serious just wasn’t in the cards for the two serial daters.
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