Rob Lowe and Winona Ryder
Here they are again, Rob Lowe and Winona Ryder, two of the most prominent figures on our list, now intertwined in a romantic relationship. Their union occurred while they were both working on the set of “Square Dance” in 1987. During this time, Ryder was just 16 years old, whereas Lowe, a bit older, stood at 23.
This quintessential ’80s couple publicly appeared at the Golden Globes the following year, solidifying their status as a high-profile pair. Their relationship endured for an impressive two-year span, leaving us with a lingering nostalgia, making us secretly wish for their reunion.
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