Top 5 Celebs who Are Famous for Their Casual Dating Lifestyle


Numerous famous people have opened up about their varied and sometimes embarrassing dating and sexual experiences. They win some, and they lose some, but it is evident that they do have some room for casual dating in their lives.

And when it comes to casual dating, it is just not possible to ignore the role online dating platforms play in making the trend popular. And the interesting thing is that many celebrities are also on these sites.

A great example is Lily Allen and David Harbour. They met through a dating app and went on a date in London. Allen revealed that she was instantly smitten with him at first glance.

So, yes, dating sites are for real, and what starts as casual dating can sometimes turn into something more serious. But, if you want to keep it short, sweet, and simple, you can try the tenderbang website, exclusively designed for casual flings.

However, if you talk about celebrities and casual dating, you just cannot forget about the following names.

1. Charlie Sheen


Even if you disagree with Charlie Sheen, you cannot dispute that he has a reputation as a playboy. He has truly led a prominent and sometimes contentious life since he rose to prominence in the 1980s.

He became one of Hollywood’s most sought-after actors thanks to roles in films like Young Guns, Wall Street, and Major League. The actor got into a lot of difficulties due to his love for partying. Sheen’s career plummeted during the ’90s as he struck rock bottom due to his substance usage issues. A constant, though, was the number of women Charlie Sheen dated at once.

Speaking of his casual dating life, you cannot ignore the fact that most of his relationships were with adult film actresses. For instance, Scottine Ross, better known by her pornographic stage name Brett Rossi, dated Sheen for about a year. Similarly, Capri Anderson, another pornstar, was famous for her flings with Charlie Sheen.

Following the breakdown of his relationship with Kelly Preston, he began dating Ginger Lynn Allen. Allen, one of the biggest stars in adult entertainment in the 1980s, stayed by Sheen’s side as he went through drug treatment.

2. Lindsey Lohan


When you are on the hunt for romance, you ought to look up to Lindsey Lohan. Or maybe not?

Since Lindsay Lohan was a teenager, her love life has been the subject of innumerable news stories. The Disney star from The Parent Trap was linked to first pop singer Aaron Carter and then Wilmer Valderrama during her early 2000s career.

Later, Lohan was harshly criticized for being in a relationship with Samantha Ronson. She has a rough love life, but it is also true that she has managed to keep her dating life under wraps for quite some time, especially since her 2016 breakup with Egor Tarabasov.

Lately, Dina Lohan, Lindsay’s mom, has confirmed that her daughter is in a new relationship. In November 2021, after nearly two years of courtship, Lindsay revealed that she was in a relationship with financier Bader Shammas.

3. Miley Cyrus


Talk about casual dating, and Miley Cyrus will shock you in more ways than you can imagine.

Over the course of her life, Miley Cyrus has dated a number of notable personalities. In fact, the singer of “Midnight Sky,” whose relationships with Nick Jonas and Tyler Posey lasted only a few months each, has been a constant source of tabloid fodder for the duration of her career.

Interestingly, Liam Hemsworth was the object of her on-and-off romance for 10 years. After getting engaged in May 2012, the couple finally married in 2018. But it all came to an end in 2019.

Interestingly, Cyrus, who is pansexual, does not mind opening up about the highs and lows of her romantic life after a relationship with Cody Simpson and a whirlwind romance with Kaitlynn Carter.

4. Jude Law


Both Jude Law and Phillipa Coan keep a low profile in public, but they both met in 2015.

It was reported in 2015 that the Fantastic Beasts actor and the psychologist first became romantically involved after meeting through common friends. After dating for four years, the pair decided to surprise their admirers by getting married in a small, private ceremony in London. Their first kid was born in 2020.

Prior to that, though, Law had a string of affairs with other famous people. There were rumors of love feelings between him and French writer Rachel Bourlier in 2015.

It was widely reported in 2008 that Jude Law dated British model Lily Cole multiple times. In 2008, he had a brief romance with Samantha Burke. A single child was born to a happy couple. Similarly, he and Catherine Harding dated and had a kid in 2014.

5. Leonardo DiCaprio


Leonardo DiCaprio is well-known for his notorious dating habits. From Rihanna to Gisele Bundchen and Blake Lively, he has been seen with almost every A-list actress in Hollywood. He has also been spotted with multiple models, singers, and actresses over the years.

Dating History

Undoubtedly one of the most popular and successful actors in Hollywood, Leonardo DiCaprio rose to fame in the 1990s starring in box office hits such as Titanic, Romeo + Juliet and The Beach. More recently, DiCaprio has been seen on screen playing the leading role in Shutter Island and Inception. But besides his career success, he may also be remembered for his celebrity dating life.

DiCaprio is famous for frequently changing girlfriends. Since becoming a hot commodity in Hollywood, Leo has been connected to dozens of starlets over the years. Among them are Gisele Bundchen, Eva Herzigová, Blake Lively and Kelly Rohrbach. His longest relationship was with Bar Refaeli which lasted from 2005 to 2011 – although they had an off-and-on again on-and-off again relationship until 2015. Most recently reported is DiCaprio’s relationship with model Nina Agdal that is said to have sparked back up in 2020 after cooling off a few years prior.

Overall, Leonardo’s dating patterns remain intriguing — while he seems quite promiscuous when it comes to whom he dates, many speculate that this could actually be due to his commitment issues rather than a desire for novelty or excitement. Whatever the reasons behind his never ending stream of relationships may be, it appears that Leo continues his casual dating lifestyle — often keeping relationships short and sweet before moving onto someone new.


There is nothing wrong with dating casually so long as both parties are on the same page. You can definitely learn from celebrities in that regard, but thankfully, you do not have to spend so much time in the limelight to impress girls. All you have to do is sign up for a good dating site, and casual dating will become a breeze.