Barbra Streisand
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Barbra Streisand 
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Barbra Streisand dated part-Armenian tennis star Andre Agassi, 28 years her senior in the early 1990s.
In his 2009 autobiography he wrote, "We agree that we're good for each other, and so what if she's twenty-eight years older? We're sympatico, and the public outcry only adds spice to our connection. It makes our friendship feel forbidden, taboo – another piece of my overall rebellion. Dating Barbra Streisand is like wearing Hot Lava."