L'OFFICIEL looks into Leonardo DiCaprio's controversial relationship timeline, including his latest girlfriend, Vittoria Ceretti.&nbsp;

Within the past year, the internet has been fascinated with Leonardo DiCaprio's interesting dating history, with many pointing out that he never dates women over the age of 25, despite his current age of 49. This claim became a meme across social media as he ended his relationship with <a href="https://www.lofficielusa.com/beauty/camila-morrone-beauty-looks" target="_blank" rel="noopener">Camila Morrone</a> after she turned 25, spiraling rumors that he only likes his women much younger than him.&nbsp;
However, DiCaprio has been seen dating women older than 25, like <a href="https://preview.lofficielusa.com/fashion/gigi-hadid-miu-miu-yevonde" target="_blank" rel="noopener">Gigi Hadid</a> briefly when she was 27. His latest relationship with 25-year-old Vittoria Ceretti seems to be promising, as they have seemingly been together for almost a year now.&nbsp;&nbsp;
Whatever your feelings on the actor's relationship history, it's definitely interesting to see who he's been spotted with over the years. From <a href="https://www.lofficielusa.com/fashion/blake-lively-style-evolution" target="_blank" rel="noopener">Blake Lively</a> to <a href="https://www.lofficielusa.com/beauty/toni-garrn-model-angel-nova-mugler-perfume-interview" target="_blank" rel="noopener">Toni Garrn</a>, L'OFFICIEL takes a look back at his dating history.&nbsp;

DiCaprio started dating <a href="https://www.lofficielusa.com/fashion/gisele-bundchen-birthday-iconic-runway-model-moments" target="_blank" rel="noopener">Gisele B&uuml;ndchen</a> when she was just 20 years old and he was 25. They dated for five years and he even took her as his date to the 2005 <a href="https://www.lofficielusa.com/fashion/natalie-portman-2022-oscars-after-party-dior-dress-took-150-hours-to-make" target="_blank" rel="noopener">Oscars</a>. B&uuml;ndchen was 25 when the relationship ended.

Bar Refaeli and DiCaprio's <a href="https://www.lofficielusa.com/pop-culture/on-again-off-again-celebrity-couples-justin-bieber-selena-gomez" target="_blank" rel="noopener">on-again, off-again</a> relationship started in 2005 when she was 20 and ended for good when she was 25. At the time of the breakup, a source said it was amicable and they just grew apart.&nbsp;

Whitney Port (2009)

No, Whitney Port and DiCaprio didn't date officially, but the TV personality just revealed that she and the actor had a six-month texting relationship years back. &ldquo;I ran into Leonardo DiCaprio at a nightclub and we proceeded to exchange numbers and had, like, a text relationship for six months&hellip;and that was really really fun,&rdquo; she told JustJared. &ldquo;We were at the nightclub and he had someone call me over. I immediately called my mom and stepped outside of the club. And then he was like, &lsquo;Come over, we&rsquo;re going to the one next door too&rsquo; and I went with my best friend. I ended up that night dropping my cell phone in a puddle of water, and it wouldn&rsquo;t turn on and I was freaking out because I was like, &lsquo;Leo&rsquo;s gonna text me and I&rsquo;m never gonna get it.&rsquo; And then I stuck it in rice and it worked.&rdquo;

<a href="https://www.lofficielusa.com/fashion/blake-lively-postpartum-body-clothes-struggle" target="_blank" rel="noopener">Blake Lively</a> had a short fling with DiCaprio for a year in 2011, when she was 23. The pair jet-setted around the world from <a href="https://www.lofficielusa.com/fashion/red-carpet-look-star-cannes-festival-2022" target="_blank" rel="noopener">Cannes</a> to New York to Los Angeles. The actress even visited him on set in Australia when he was filming The Great Gatsby.&nbsp;

Former <a href="https://www.lofficielusa.com/pop-culture/rise-and-fall-victorias-secret-timeline" target="_blank" rel="noopener">Victoria's Secret</a> Angel Erin Heatherton dated DiCaprio for 10 months when she was 22. Again, the split was said to be amicable.&nbsp;

Another <a href="https://www.lofficielusa.com/fashion/victorias-secret-first-black-transgender-model-emira-dspain" target="_blank" rel="noopener">Victoria's Secret</a> Angel, Toni Garrn, spent 18 months in a relationship with the actor. She turned 21 in their time together and allegedly broke things off after photos came out of DiCaprio leaving a nightclub with multiple other women. Since then, however, the pair have been spotted together and seemed to have no bad blood.

The <a href="https://www.lofficielusa.com/pop-culture/megan-thee-stallion-leyna-bloom-naomi-osaka-sports-illustrated-swimsuit-2021-cover" target="_blank" rel="noopener">Sports Illustrated</a> model and Baywatch actress spent six months with the actor before they split. They were even at the center of <a href="https://www.lofficielusa.com/pop-culture/most-expensive-celebrity-engagement-rings" target="_blank" rel="noopener">engagement</a> rumors, which were disproved at the time. The breakup was amicable and was reportedly just because of conflicting schedules.&nbsp;

DiCaprio spent two years together with <a href="https://www.lofficielusa.com/politics-culture/mara-martin-breastfed-sports-illustrated-runway" target="_blank" rel="noopener">Sports Illustrated</a> model Nina Agdal. They eventually split when Agdal was 25 and a source close to them said he just wasn't ready to settle down.&nbsp;

For his longest relationship since his split with <a href="https://www.lofficielusa.com/pop-culture/gisele-bundchen-tom-brady-wife-cutest-moments-instagram" target="_blank" rel="noopener">B&uuml;ndchen</a> in 2005, DiCaprio started dating <a href="https://www.lofficielusa.com/film-tv/models-who-became-actresses-twiggy-sienna-miller" target="_blank" rel="noopener">model-turned-actress</a> Camila Morrone when she was 20 years old and he was 42. The couple made their first public appearance when they sat together at the <a href="https://www.lofficielusa.com/fashion/oscars-2020-red-carpet-looks" target="_blank" rel="noopener">2020 Oscars</a>. Even though it was reported that the actor was considering an engagement, the pair ended things in August 2022, two months after Morrone's 25th birthday.&nbsp;

<a href="https://www.lofficielusa.com/film-tv/kate-winslet-talks-leonardo-dicaprio-life-long-friendship" target="_blank" rel="noopener">DiCaprio</a>&nbsp;was pictured with supermodel <a href="https://www.lofficielusa.com/pop-culture/gigi-hadid-recipes-pasta-instagram" target="_blank" rel="noopener">Gigi Hadid</a>, 27, at a party in New York City during <a href="https://www.lofficielusa.com/fashion-week/look-inside-nyfw-parties-events-spring-summer-2023" target="_blank" rel="noopener">NYFW</a> in September 2022. The <a href="https://www.lofficielusa.com/film-tv/leonardo-dicaprio-birthday-facts-titanic-kate-winslet" target="_blank" rel="noopener">Titanic</a> actor, famed for only dating women 25 and younger, was seen getting cozy with Hadid. &ldquo;They are taking it slow,&rdquo; <a href="https://pagesix.com/2022/09/13/new-couple-leonardo-dicaprio-and-gigi-hadid-spotted-at-nyfw-party/" target="_blank" rel="noopener">Page Six</a> confirms. Sources told <a href="https://people.com/style/leonardo-dicaprio-and-gigi-hadid-hanging-out-getting-to-know-each-other-sources/" target="_blank" rel="noopener">People</a>, &ldquo;they are getting to know each other.&rdquo; This relationship is the first time DiCaprio has publicly dated a woman older than 25.

Victoria Lamas (2022-2023)

In early 2023, the actor was spotted hanging out on a yacht in St. Barts with model Victoria Lamas. &ldquo;I know she likes him very much,&rdquo; Victoria&rsquo;s father Lorenzo Lamas told the&nbsp;<a href="https://nypost.com/2022/12/29/lorenzo-lamas-daughter-victoria-smitten-with-leonardo-dicaprio/" rel="nofollow noopener" target="_blank" data-ylk="slk:New York Post" class="link " data-rapid_p="27" data-v9y="1">New York Post</a>&nbsp;in December 2022. &ldquo;I think they met last month.&rdquo;&nbsp;

Eden Polani (2023)

DiCaprio became romantically linked to 19-year-old model Eden Polani after a series of paparazzi shots surfaced of the two together. Fans of DiCaprio were quick to call out that Polani is younger than some of the actor's oldest movies. However, <a href="https://www.tmz.com/2023/02/07/leonardo-dicaprio-not-dating-19-year-old-eden-polani/" target="_blank" rel="noopener">TMZ</a> reported that the rumors about DiCaprio and Polani aren't true. According to sources, the pair were just sitting next to each other in a group of people at a party.

Irina Shayk (2023)

DiCaprio was spotted with Russian model <a href="https://www.lofficielusa.com/fashion/irina-shayk-model-street-style-daughter" target="_blank" rel="noopener">Irina Shayk</a> several times throughout Coachella Weekend 1. The two&nbsp;enjoyed <a href="https://www.lofficielusa.com/music/frank-ocean-headlining-coachella-music-festival-2023" target="_blank" rel="noopener">Frank Ocean</a>&rsquo;s <a href="https://variety.com/2023/music/news/frank-ocean-coachella-set-what-went-wrong-1235586157/" target="_blank" rel="noopener">chaotic set</a> after partying with several friends, including model Stella Maxwell, the night before.

First spotted together in August, the controversial pair spent time together on a yacht with other models including Meghan Roche and Imaan Hammam. They were also spotted on Halloween getting frisky together, and then for <a href="https://www.lofficielusa.com/pop-culture/leonardo-dicaprio-best-90s-moments-young-heartthrob" target="_blank" rel="noopener">Leo's</a> 49th birthday party in November. Although there have been rumors of an engagement, these have been shot down, however, the pair is still together despite the 20-year age gap.&nbsp;

A Deep Dive into Leonardo DiCaprio's Dating History

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