#23: Rihanna and Pharrell Williams

Around 2009, Pharrell Williams and Rihanna set the rumor mill ablaze with whispers of a budding romance, fueled by sightings of Pharrell leaving her place multiple times. Time has since ushered them along separate paths, with Rihanna recently celebrating the arrival of her second child with ASAP Rocky.

While their dalliance may have been brief, it’s abundantly clear that the potential for something special was there. Exhibit A – this enchanting holiday family photo that oozes beauty and cuteness – offers a tantalizing glimpse into what could have been.