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My first wife was almost 30 years older than me, we lasted for 6 years.

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age is not relative if you like the person

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That's up to you. Hugh Hefner comes to mind, but maybe not a great example.

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Of course you can date him.

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i say he is the clear winner in that sitch

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yes there is nothing wrong with that it's just a little weird.

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It depends on the 25 year old and the 40 year old. Jerry Seinfeld and Paul Simon seem like two success stories.

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Sure. My first wife was about 15 years older than I. My current one is 13 years younger.

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