Celebrities Who Have Dated Porn Stars

Gene Simmons, the lead singer of Kiss and star of the reality TV series Gene Simmons Family Jewels, has been in a relationship with former adult star and 1982 Playmate of the Year Shannon Tweed for 33 years. They met at the Playboy Mansion in 1983. They were together for 28 years before finally getting married in 2011. They have two children, Nick and Sophie Alexandra. They claim the secret to a long relationship is mixing things up in the bedroom. “Keep having sex in different ways. Try to think of something new,” Shannon Tweed suggests. Gene Simmons is famous for his luck with the ladies, but Shannon denies the rumors that they have an open relationship. "Anything that you've ever seen... happened before 1983.”

There are many celebrities who have dated adult stars, but not many that have dated five of them. Movie and TV star Charlie Sheen has been with porn stars Capri Anderson, Bree Olson, Ginger Lynn, Melanie Rios, and his current fiancée Brett Rossi. His relationship with Ginger Lynn was among the longest, and lasted five years, from 1990 to 1995. They met on the set of Young Guns II, in which Charlie’s brother Emilio Estevez starred. Charlie gives her credit for inspiring him to pursue sobriety when he was struggling with addiction to drugs and alcohol and giving the strength and support he needed to be successful. They remain friends to this day. However, Ginger Lynn warned Charlie Sheen’s fourth fiancée, twenty-four-year-old Brett Rossi, “This won’t be his last marriage.” Which is a very reasonable warning to give a man’s fourth fiancée.

Jesse James and the stripper and porn star Janine Lindemulder were married from 2000 to 2004. They allowed the Discovery Channel to document their wedding and the first few months of their married life. Janine was caught on film physically attacking Jesse just hours after the wedding! They have a daughter together named Sunny over whom a bitter custody battle was fought in 2010, in which Janine’s drug use and even an incident of prostitution were used as arguments. Janine was arrested in 2011 for harassing Jesse James about their daughter. Janine once referred to Jesse James as a “chronic cheater.” Not all celebrities who have dated porn stars have enjoyed a happy ending, or even a happy beginning.

MMA star Tito Ortiz was in a relationship with porn star Jenna Jameson from 2006 to 2013. They met on MySpace. They have a pair of seven-year-old twin sons named Jesse and Journey, of whom Tito gained custody after the couple’s divorce in 2013. This is another rocky relationship which has made headlines. There were accusations made by Jenna of domestic violence in 2010. However, he was quickly released after being arrested and claims that she filed the report because she was angry that he confronted her about her OxyContin addiction. When they got divorced Jenna took the break-up very hard. A former assistant of Jenna’s claimed that she had been abusing Xanax, Suboxone, Ambien, and alcohol to cope with the break-up. Tito had to file a restraining order against Jenna because she was cyber-bullying his new girlfriend Amber Miller.

Out of the celebrities who have dated adult stars, Drew Carey, host of The Price Is Right, has had one of the most successful relationships. After Drew broke up with his fiancée Nicole Jaracz in 2012, he and Megan Martinez met on the adult webcam site Myfreecams.com. After sending her some gifts he met her in person in Las Vegas at the Adult Video News Awards. He soon flew her and her nine-year-old son out to his Hollywood mansion, then bought the two of them a home and started paying for everything in their lives. Drew intends to stay with her, but will not marry her until her webcam career is over, as he does not want other people seeing his wife naked. He is often referred to as her sugar daddy, which makes sense seeing as he is worth $165 million!

Evan Seinfeld, musician and founding member of the influential band Biohazard, was in a relationship with porn superstar Tera Patrick from 2001 to 2009. They were married in 2004 and divorced in 2009. Evan also stars in adult films, and performed in seven scenes with Tera. The break-up resulted from Evan’s refusal to stop acting in adult films. Tera Patrick wrote, “I said to Evan, 'I'm your wife, and that is the strongest bond two people should have, and that should come first. I've moved on from porn. And I want you to stop. You promised me you'd only do porn for a few years. Your few years are up.'” However, he did not listen and they got divorced in September of 2009. A few months after the divorce Evan literally said in an interview with the New York Post, “She's not a sexual person. We barely had sex in our own marriage.” Pretty hard to believe, if you ask me. This story is proof that acting in adult films and monogamy don’t mix well! Nonetheless, Evan and Tera remain business partners to this day.

Jennifer Capriati was once the number one female tennis player on the planet and is a member of the International Tennis Hall of Fame. She dated adult film star Dale DaBone (real name Dale Rutter) from 2003 to 2009. This is another relationship that ended badly. In 2010 Jennifer was rushed to the hospital after overdosing on prescription medication in a possible suicide attempt. Dale DaBone claimed that this happened because she was stressed out about his return to the adult film industry, which took place just a few months after the relationship ended. In 2013, Jennifer was charged with stalking and battery for an altercation she got in with Dale on Valentine’s Day at a fitness club in Florida. However, the charges were dropped.

Former UFC light-heavyweight champion Chuck Liddell was in a relationship with Jayden James in 2009. Rumors started when the two were spotted partying together in a strip club and Chuck broke up with his fiancée Erin Wilson soon after, although Chuck claims that the sighting was not the cause of the breakup. After the relationship ended, Chuck claimed that Jayden had used him for his fame in order to advance her career. At the beginning of that year, Jayden, MLB pitcher Brad Penny, and Chuck were partying in Mexico and Jayden posted photos of it all over the internet and made a YouTube video with a monologue describing her time with the high-profile athletes in Mexico. Chuck called her and told her to take the photos down, but she didn’t, which was an indication of her true priorities. Sometimes celebrities who have dated porn stars have actually been manipulated from the start!

Monster Garage star and motorcycle master Jesse James felt the wrath of the pop culture public when he cheated on his then-wife, film star Sandra Bullock. Cast as the bad guy, James leaned in to the persona and revealed a string of affairs. But before Bullock, there was Janine. Adult film star, Janine Lindemulder, said “I do” to James in October 2002, but it came to an end just over a year later when Lindemulder was pregnant with their child, Sunny.

Women, stand up and represent! It’s not just men who date the porn stars. Former tennis star and member of the International Tennis Hall of Fame Jennifer Capriati began a fling with adult film star Dale DaBone (real name Dale Rutter) in 2003 that eventually turned into an on-again, off-again relationship. In a 2010 interview, DaBone said, "I was in love. The porn thing came out and I had to hide it so I quit porn. It caught up with us. We couldn't go anywhere together because they would just rip us apart. I went above and beyond because of the porn thing and she cheated a bunch … What can you do? It really killed me." But then in a later tweet, DaBone claimed Capriat’s depression and overdose was related to him getting back in the porn game.

Golf superstar Tiger Woods not only had an affair with a porn star, it cost him his marriage and nearly his entire career! In 2010, adult film actress Joslyn James made an intimate text conversation between her and Woods public. In it, Woods refers to a threesome that they shared. His then wife, Elin Nordegren, was furious and dissolved the marriage, taking down Woods’ cookie cutter, good boy image with it. Woods was rapidly dropped by multiple sponsors as the hits kept coming, and it was revealed he had affairs with more adult film actresses, Devon James and Holly Sampson.

The musician has dated his fair share of adult film stars and at times it seems that may be the main characteristic he looks for in women. There was Jesse Jane (real name Cindy Taylor), whom he allegedly dated for around a year in 2004, and, in 2006, there was Briana Banks (real name Briana Bany). And, if you believe his songs, there have been countless others.

Founding member of the heavy metal band Biohazard, Evan Seinfeld didn’t just date an adult film actress, he eventually married her. Seinfeld met adult film star Tera Patrick in 2001, and the couple was married in 2004. The marriage lasted seven years but even after it ended they remained on good terms and continued work together at the company they formed together, Teravision. Said Seinfeld at the time, “I look forward to continuing to represent the Tera Patrick brand and support all of her endeavors. She is forever in my heart.”

Acting superstar Michael Keaton has done it all in his iconic Hollywood career. He has played Batman, defined Beetlejuice and hooked up with a porn star. Keaton met adult film actress Serina Robinson on the set of Clean and Sober where she was playing a naked corpse. Keaton claims it was only later in the relationship that he discovered Robinson had once worked in adult films under the alias Rachel Ryan. In addition to Keaton, Serina Robinson/Rachel Ryan has also been linked to Jack Nicholson and was even married to the star of Empty Nest, Richard Mulligan.

The titular star of The Drew Carey Show and host of The Price Is Right may have a family friendly image to the general public, but his private persona is decidedly more adult. Unlike many of the stars on this list, Carey was well aware of Sklyer’s, (real name Megan Martinez) status as an adult film actress. In fact, that’s how they met. Carey engaged Martinez in some private video sessions on the website MyFreeCams.com before eventually she and her son moved into Carey’s home.