Some of these former celebrity relationships – and the fact that they almost tied the knot – may surprise you.

Evan Rachel Wood and Marilyn Manson

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Yes, these two were once an item. They first met in 2006 (Rachel was just 18; Marilyn was 37), and got engaged in 2010. Soon after, though, they split up. Check out Evan in his raunchy music video for ‘Heart-Shaped Glasses’:

Jennifer Lopez and Ben Affleck

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Jen and Ben got engaged in 2002, and he was her costar in ‘Jenny From The Block’. The super-couple ended things in 2004, after which Jennifer began dating Marc Anthony, who she eventually married.

Ryan Reynolds and Alanis Morissette

surprising celebrity engagements Ryan Reynolds Alanis Morissette

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Perhaps the most surprising couple on this list, Ryan and Alanis dated for two years and got engaged in 2004. However, the relationship eventually began to go downhill, and they decided to call it quits in 2007.

Julia Roberts and Kiefer Sutherland

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The Oscar-winning actress and Kiefer were briefly engaged in the early ’90s. They broke up three days before their wedding. Two years later, she married singer Lyle Lovett.

Winona Ryder and Johnny Depp

The Stranger Things star and Johnny had a swift engagement but ended things in 1993. While they were together, Johnny got a tattoo that read ‘Winona forever’ – which he promptly changed to ‘Wino forever’ soon after their break-up.

We still love them in Edward Scissorhands, though…

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