A Brief History Of Leonardo DiCaprio's "25 & Under" Girlfriend Streak

And finally, we've arrived at the It Couple of the early aughts. Although the Titanic star was linked to plenty more supermodels throughout the 1990s (Naomi Campbell, Eva Herzigova, Amber Valletta, and Helena Christensen to name a few) his buzzy relationship with Gisele Bündchen, which started when he was 24 and she was 18, can be considered the last of his, well, "age-appropriate" affairs. It was all uphill for him, and downhill for his girlfriends (age-wise, at least), from here.

Rumor has it that Leo spotted Gisele on the catwalk in 1999 and decided to seek her out. Lucky for him, the Brazilian beauty was also smitten and the pair sizzled until they fizzled out in 2005. The nature-lovers biked, walked their dogs, visited the Amazon rainforest, and attended basketball games together long before Leo had courtside seats. And, to this day, she's still the only girlfriend to have accompanied him to the Oscars.

Surprise, surprise, she was around 25 when they officially split, however she's the one who apparently walked away to do some inner work on herself. As she wrote in her 2018 memoir, "Was I alone in wanting to do some serious soul-searching while he stayed the same? In the end, unfortunately, the answer was yes." Talk about foreshadowing.