David Letterman’s question that left Jennifer Aniston very uncomfortable

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David Letterman, once a late-night icon, is now facing renewed scrutiny over past interviews that haven’t aged well—especially with female guests.

One uncomfortable moment resurfaced from a 2006 interview with Jennifer Aniston, who was promoting The Break-Up. What began as a typical chat turned awkward when Letterman focused on Aniston’s legs, leaving many viewers uneasy then—and even more so now in today’s cultural context.

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