Whitney Port refused to have a one night stand with Leonardo DiCaprio

Whitney Port

I was too old to enjoy The Hills, and I never watched The City. Whitney Port starred on both MTV reality shows, and she’s currently in The Hills: New Beginnings. I was looking through her Wiki and I sort of respect the way she’s consistently worked on various projects and reality shows and yet never seemed crazy or over-the-top. Mostly, my vibe is that she’s kind of bland but harmless. Well, Bland Whitney also has a podcast, just like your beloved CB and Kaiser (ME!). Her podcast is With Whit, and on the latest pod, she spills one of her best gossip stories. Honestly, if this had happened to me, I would have told this story EVERYWHERE. I would have run to Entertainment Tonight as soon as it happened. You see, Whitney has a Leonardo DiCaprio story. And it’s a fun one:

She’s happily married and has one son with her husband. But Whitney Port reminisced on one of her ‘bigger regrets’ in life during an episode of her With Whit podcast released on Tuesday. The 34-year-old reality star admitted she had a wild night with Leonardo DiCaprio nearly a decade ago and turned down his advances after six months of texting. Port sat down with her ‘best friend of life’ Andrea Cuttler for the 14th episode of her self-titled podcast and spilled ‘spill a secret I have been dying to share for so long.’ She asked Andrea to recount the events leading up to meeting Leo at a club after she chatted it up with Rihanna.

‘I have been dying to tell people this story for ages,’ she said. ‘I feel like whenever I tell it to friends, no one believes me.’ The girls were ecstatic recalling when Whitney walked up to Rihanna at the club to tell her that her ex-brother-in-law wrote her hit SOS, only to find out that the Barbados-born beauty was a huge fan of The City. ‘And then Leo comes up to you to also … insinuated that, like, he had missed the week priors episode,’ Andrea recalled. ‘And you’re like, is he telling me that he watches The City? This is very confusing, but also incredible.’

Andrea said ‘there was a phone number exchange’ before the ladies walked to another club with Leo and his pals. ‘I remember dancing alone on the dance floor because you were in the corner talking to him and I didn’t want to intrude, but also like couldn’t leave,’ Andrea said.

‘I feel like I was getting drunk at that point,’ Whitney said. ‘I don’t remember … it’s such a shame.’

Their night out wasn’t the end of the road for Whitney and Leo as she revealed the pair had a ‘BBM relationship for like six months’ before meeting up again in LA. At the time, Blackberry smart phones were a popular accessory and people regularly used Blackberry Messaging (BBM) as a way to text friends.

‘He invited me out to Teddy’s and he invited me back over to his house and I said no,’ Port revealed. Andrea loved the story and laughed as she asked if Whitney was the only girl to ever turn down DiCaprio. ‘I was too nervous,’ Whitney said. ‘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. If you didn’t think I was cool, now you probably do.’

[From The Daily Mail]

“I didn’t want to be with him alone. I was way too nervous to do it…” I also would not want to be alone with Leo, but then again, he doesn’t want to be alone with me either! Besides, I bet Leo even brings his wingmen home to sit on the couch and play video games while Leo takes a lady to the back bedroom so she can do all the work while he looks bored. But… all of the other details are kind of amazing. Rihanna watched The City! Rihanna and Whitney chatted! Leo hadn’t seen the most recent episode! Leo did the approach himself! That’s how you know it was a while ago – Leo was doing “the approach” himself. Also, he actually texted a woman for months without actually sleeping with her? *chuckle*

Leonardo DiCaprio

Photos courtesy of WENN.

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28 Responses to “Whitney Port refused to have a one night stand with Leonardo DiCaprio”

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  1. Everley says:

    One of her biggest regrets? Learn to love yourself girl.

  2. Jb says:

    I never saw the sexual appeal of Leo… I loved titanic and obviously loved the romance as a freshman in high school but he never made my iceberg melt!

    • smcollins says:

      “never made my iceberg melt”

      I’m dying! 😂 And I know exactly what you mean. I’m the same age as him and he’s never done anything for me. I think he’s a great actor and I love watching him, but that’s it. No feelings of lust or anything.

    • 2lazy4username says:

      I’m in the same club. But then again, I also never found Brad Pitt to be hot.

    • Ronaldinhio says:

      He looked like a fetus for far too long and now looks like a wide faced Jack Nicolson
      He also never floated my debris

    • Turtledove says:

      Agreed. I am a fan of his movies, and swooned at the romance of Titanic, but never found him hot.

      Wait..no….I did..ONCE. He has a sexy scene in the Departed with Vera Farmiga and he was actually hot there. It was not a long drawn out scene, but something about their chemistry worked. Then I saw him with Margot in Wolf of Wall Street, and I thought “I bet that is excatly what he is like and real life…no thanks!” lol

    • SuperStef says:

      Yes! I always appreciated his acting talent but he never kept my debris door afloat for two…

    • K says:

      Yeah, he was cute and a little intense in his 20′s, but not really hot. Just never thought of him that way.

  3. Kitten says:

    LOL that’s an awesome story. I can TOTALLY see Leo trying to hook up a one-nighter with her. She’s definitely his type, physically.
    But I could see Leo thinking that he wouldn’t want to be papped with a reality TV star because that’s beneath him LOL.

  4. Susie says:

    I hope she was joking about it being a regret. it seems like her gut was telling her that being alone with him was not a good idea and there is no need for her to compromise her values ( even for Leo) just to have a one night stand a possibly fun .. or scary … story about it.

    • Kate says:

      lol sometimes I “regret” not hooking up with a couple hot guys in college that wanted to but then I realize the same thing that there was a reason in my gut that I didn’t at that time and so it was the right decision. Plus I feel like fantasies about what didn’t happen tend to be way hotter than any memories of things that actually did happen (TMI?)

  5. lucy2 says:

    I can believe he hit on her once, but not that he tried for 6 months.

  6. Valiantly Varnished says:

    I kind of get what she means. It would have made for a great story. But she still got a great story without sleeping with him. And let’s be honest: stating in 2019 that you’ve slept with Leo would only illicit an “ewww” response. So…she dodged a bullet. And STILL got a great story out of it. Lol

  7. Lala11_7 says:

    I would have left nothing but sheets and his headphone set….

  8. MCV says:

    he seems like the type of guy that puts 0 effort and let’s the girl do everything for him (in sex and on every other matter so it was a good decision on her part…)

  9. Kimmy says:

    That story is amazing!! Binging the Hills was #1 on my list while on maternity leave. I’m the same age as those girls and man, it brought back memories! I was always #teamLauren. Whitney was super vanilla, but drop dead gorgeous. I tried one ep of the reboot and it was so freaking bad, I couldn’t finish it.

  10. line says:

    I have a cousin who was modeling, to be able to pay for her medecine studies, she also told us a similar story about Dicaprio. It was in 2007, her agency had organize an evening in which there was Dicaprio and her friends. During the evening she and her friends were invited to his table. My cousin is totally his type, she is tall, blonde, green eyes, consequently at the end of the evening, Dicaprio offer to join him in his hotel, she refused because his guts told him that being alone with him was not a good idea and she did not need to compromise her values even for Leo just to spend a night no doubt fun or scary ….

    But unlike Whitney Port, she has no regrets, because now she has become a cardiologist, she is married and has two beautiful boys.

    • Fluffy Princess says:

      Wow! That story is just as great as Whitney’s! PLUS, she’s a cardiologist? How impressive! She definitely got a better happy ending not being with him, and yummy piece of gossip!!

  11. My3cents says:

    To be fair he has evolved. He’s dating a brunette now.

    • PlainJane says:


      Or casting a wider net!

    • lucy2 says:

      I guess her being half his age balances out the non-blondness.

    • JKng says:

      Cami is the best he can do right now; all the blondes wanted too much and demanded couple pics for their IG account. He did not want to do that and is stuck with an average LA girl. Go search – Polish model Ela Leo DiCaprio. She was next up, but things fell through.

      I doubt Cami is even giving him oral or handjobs. At the McCartney concert he was four people away form her the whole night and paid her not attention.

  12. Wellsie says:

    This story is very enjoyable. Juicy gossip and no one was violated! Huzzah!

  13. PlainJane says:

    He is so gross, I really don’t get it. Seems like something to be proud of, that she turned down the walking STD.

    You know it’s true that he does “…brings his wingmen home to sit on the couch and play video games while Leo takes a lady to the back bedroom so she can do all the work while he looks bored…”

    She dodged a bullet.

  14. Izzy says:

    Dodged that missile, hon.

  15. Krissy says:

    Oh my how my teenage heart loved him back in Titanic!