Why The Hills Star Whitney Port Turned Down Leonardo DiCaprio
Whitney Port rose to fame after appearing on MTV's "The Hills" back in 2006. Port's fresh-faced beauty and drama-free personality caused fans to love her so much that she nabbed a spin-off show called "The City" (via People). The reality show was set in New York City and followed Port's life as she chased her dreams in the fashion industry. During her time on "The City," Port's tumultuous relationship with Jay Lyon was highlighted on the show, per Glamour. On the series finale, which aired in 2009, the Tamarama band member dumped Port to go on tour.
In 2010, Port moved on with "The Buried Life" star Ben Nemtin (via People). The two reality TV stars looked quite smitten at OK! Magazine's 5th Anniversary Party the same year, per HuffPost. However, after a little more than a year together, Port and Nemtin broke up in 2011 (via Us Weekly). While it seems that these days, Port has put her histories with her ex-boyfriends behind her, there was one potential romance with a celebrity that remains her biggest regret.
Whitney Port was afraid to be Leonardo DiCaprio's one-night stand
Leonardo DiCaprio is one of Hollywood's most eligible bachelors, and has been linked to many beautiful women. The actor seems to have a penchant for models, and his long list of former girlfriends includes Bridget Hall, Naomi Campbell, Helena Christensen, and Gisele Bündchen, per Marie Claire.
Whitney Port could have been DiCaprio's distant memory, but she gave up the chance years ago. On a 2019 episode of her podcast "With Whit," the reality star shared that she met DiCaprio at a party in New York City in 2009 and the two subsequently started messaged each other for several months. DiCaprio asked Port out on a date and while they did end up going out, she wasn't able to see it through. "He invited me back over to his house and I said 'no," she revealed. "I was nervous. I had never had a one-night stand. I didn't want to be with him alone ... I was way too nervous to do it and then I lost my chance and it's really one of my bigger regrets in life."
Although Port may regret not going home with the "Don't Look Up" star, she eventually found her happy ending with husband Tim Rosenman.
Whitney Port has no regrets about marrying Tim Rosenman
Whitney Port met her now-husband Tim Rosenman while filming "The City" (via the Daily Mail). Although they became close friends during filming, they didn't start dating until 2012 and got married in 2015. "It's such a great feeling! We finally get to stop saying fiancé and be husband and wife! We really always knew we would end up together and now we can start a new amazing chapter in our lives," Port told Us Weekly at the time.
In July 2017, Port and Rosenman welcomed their first baby together. "Sonny Sanford Rosenman was born on 7/27/17! Everyone is so happy and healthy and we are home now," she wrote on Instagram. Port told fans that she was "beyond obsessed and in love" with her son, and promised to try not to make her Instagram feed all about her new baby. In November 2021, Port shared the heartbreaking news that she miscarried after announcing that she was pregnant (via) E! News. "I'm so sad to say this, and some of you may have watched our latest YouTube episode, but lost the baby. We found out yesterday. I don't even really know what to say here," she told fans via an Instagram Story (via E! News).
As of this writing, Port is still trying for a second child, sharing that she was thinking about going the IVF route, per E! News. With Rosenman by her side, Port can't have too many regrets about her missed chance with Leonardo DiCaprio.