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As much as we don't want to, we can't help but feel a little bad for Tiffany Trump. Arguably the one First Child with the most to prove, Tiff seems to try hard to appease everyone - from sharing her low-key liberal leanings on social media to doing just about anything to get her dad to like her. But still, she can never quite win. Case in point: her 27th birthday week in Miami.
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