There’s a fascination surrounding romances in Hollywood; perhaps that’s because so many of them end in disaster in such a short time, or maybe it’s because celebrities seem more normal when we see them fall in and out of love. Whatever the reason, when it comes to love, no one has a more interesting story to tell than Lindsay Lohan.

Lohan’s love life is far more fascinating than your average celebrity's, and that’s because she has been linked to so many unexpected men (and women) over the years. Some of the reports about her relationships are so bizarre you need to see evidence to believe the odd coupling — and lucky for us, this evidence exists. She's been linked to Aaron Carter (whose actions resulted in a girl feud), and James Franco, whose name was scribbled on a kiss list, and many surprising people in between. Yes, it seems the actress has gone from being the entertainment industry’s IT girl, to having a relationship list which features more A-list celebs than her movies ever did.

This may seem harsh, but after you read about these 15 men who are believed to have romanced Miss Lohan, you'll understand what we mean.

Wilmer Valderrama Was Careful To Keep Their Relationship A Secret

Lindsay Lohan and Wilmer Valderrama met on That '70s Show, when she appeared in the episode, Mother's Little Helper. And they must have hit it off because they are reported to have started dating in May of 2004. Although, that time frame is disputed because it is believed that the couple chose to keep quiet about their romance and only make it public in July when Lohan turned 18.

Although when it was public, Valderrama, who is six years Lohan’s senior, wasn't afraid to share his thoughts on the relationship. He told People magazine, “We try to keep it more under wraps because it is a lot more meaningful that way. At this point, we don’t need all the free press.”

It may have been special, but it wasn't meant to last, and by November the couple revealed, via their reps, they had called it quits but would remain friends.

Gerard Butler Was Not Afraid Of A Little PDA

Not long after Lindsay Lohan’s split from Samantha Ronson, she and Gerard Butler reportedly found themselves on holiday together in 2009. They both attended the launch of the Sol Kerzner Mazagan Beach Resort in Morocco; and what better place for love than a beach resort?

The Mirror (via Marie Claire) reported on how the pair were seen dancing together and sharing a smooch in the VIP area. But it seems Lohan’s relationships are about as successful as those found on The Bachelor and The Bachelorette, because Who’s Dated Who claims it was just one day that this coupling lasted.

Fast forward a few years to 2012 though, and Lohan and Butler were spotted together at West Hollywood’s Chateau Marmont. According to People magazine, the pair were seen laughing together and telling jokes, which would suggest that they didn't end on bad terms.

Was It All Work And No Play With 50 Cent?

Of all the men who Lindsay Lohan has been linked to over the years, and there have been a lot (some true, and some, definitely false), the most bizarre coupling was between her and rapper 50 Cent. According to Who’s Dated Who, Lohan and 50 Cent were first linked in December of 2010 but split one month later.

Not much is known about their time together, although, if you want any information about Lohan’s life you can always rely on her father, Michael Lohan, for a comment. According to NME, he told Life and Style that his daughter and 50 Cent were thinking about collaborating. He said, “They’re talking about working together. Nothing’s firm yet, but they’re in talks. They’ve actually known each other for a while, just from being in the business together and crossing paths at events.”

Harry Judd Was Excited To Spend Time With Her

Harry Judd is best-known for being a band member of hugely popular British boy band, McFly, but something else you should know about him is his apparent romantic link to Lindsay Lohan.

The pair reportedly met when the band had a cameo in the movie, Just My Luck (some publications also link Lohan to her co-star, Chris Pine, during this film), and Lohan must have thought Judd was cute because he claims she invited him to hang out. Judd shared his story with The Mirror years later, telling the publication how he had thought it was awesome.

He recalled, “At the time I thought, ‘This is awesome.’ But I was really nervous. Lindsay invited me back to her hotel. I left at eight o’clock next morning.” But according to the publication, Lohan denied that anything happened.

Aaron Carter's Actions Sparked A Feud

This is probably the ugliest relationship link that Lindsay Lohan has had over the years, and that’s because Aaron Carter is believed to have dumped his girlfriend, Hilary Duff (who he had been dating for a year and a half), to be with Lohan. According to Buzzfeed, Carter later said, “I was dating [Hilary] for like a year and a half, and then I just got a little bored so I went and I started getting to know Lindsay."

The timeline of this relationship dates back to late 2002 (they were only teenagers at the time), and according to The Sun, the new couple dated for a few months before Carter decided to go back to Duff.

But why is this an ugly relationship? Well, for starters, Carter proved he was pretty fickle when he decided to break up with his girlfriend for Lohan, only to go back to her a few months later, and the worst part is his actions caused a feud between the two women.

Brody Jenner Would Have Been Great For Lindsay

When you think of Brody Jenner you probably think of the Kardashian clan, after all, he was their half-brother for a long time, but Jenner’s romantic relationships are just as interesting as his family ones, and in 2008, he was linked to Lindsay Lohan.

According to People, the pair was spotted at two nightclubs, and a source told the publication how they were “all over each other” at Beatrice Inn. The source also revealed that although it was early days these two were “more than friends” and that they actually really liked each other.

The public also liked them as a couple because Jenner would have been good for Lohan, but this relationship was never publicly confirmed. And to make it even more complicated, Jenner was also linked to Cora Skinner around the same time.

James Franco Was One Of The Men On Her Kiss List

James Franco and Lindsay Lohan are believed to have had a brief fling in 2005, at least, according to a handwritten list the actress wrote, detailing all the men she had been with over the years. The list was published by InTouch and included a lot of really surprising names, and among them was James Franco.

But whatever happened between these two obviously didn’t end on good terms, at least not if Franco’s awkward comments about Lohan are anything to go by. When her list was published, he gave an interview to Los Angeles Magazine (via Us Weekly) denying any romantic link between the two of them. He said, "And Lindsay herself has told lies about me with her people she's slept with list! So I feel like what I said is much less than what she's said."

Chris Pine May Have Been More Than Her Co-Star

Lindsay Lohan and Chris Pine starred on the 2006 film, Just My Luck, and there may have been more than just onscreen romance happening between these two. Reports claim they were together, at least at some point, during filming.

At the time, Pine’s career was just starting out, while Lohan was at her peak, which was something that fascinated Pine. He told The Hollywood Reporter, “It was a real cyclone of insanity, like being around The Beatles. It was fascinating to watch, and in hindsight, it’s really a distinct moment in someone’s life when you see what’s really wonderful about what we get to do and what’s really dangerous about it.”

He may have been willing to comment on what it was like working with Lohan, but as far as dating her was concerned, well, he was a lot quieter on that topic.

Did She Really Want Us To Believe Jason Segel Was A Coworker?

There is some confusion about what exactly happened between Lindsay Lohan and Jason Segel, but there is no denying one thing, she was photographed leaving his home in December of 2009. According to The Superficial, the actress was spotted leaving Segel's home and getting into his assistant’s car. This moment made headlines and proved that if you want to hide something from the paparazzi, chances are it’s not going to happen.

Does this mean they were a couple? Absolutely not, but the evidence does seem to suggest that they briefly had some romantic connection, or at the very least spent time together. Although, Lohan would want you to think otherwise because she reportedly took to Twitter at the time claiming she was just having a meeting at a “coworkers” house. Okay, Lindsay, if you say so!

Calum Best And Lindsay Ended On Bad Terms

The British reality TV star, Calum Best, has been linked to many women, and one of them happens to be Lindsay Lohan.

Best and Lohan briefly dated in 2007, after meeting in London at the nightclub, Kabaret. Their romance was apparently fiery, and when they called it quits, it was no different because they are said to have parted very badly.

In 2015, Best reflected on his relationship, telling Perez Hilton he and Lohan no longer talk. He added, “It was a mad time in my life and I was pretty scr**ed up. That and the press combined didn’t help the situation, so it didn't quite work out.” He also revealed he didn’t know why they ended on such bad terms, but he thought she was a “lovely” girl.

Justin Timberlake May Have Caught Lindsay’s Eye

Remember that romance hit list I mentioned in an entry above? Well, James Franco wasn’t the only famous man to find himself on it; Justin Timberlake was another big star who Lohan claimed to have had a fling with.

If the rumors are true, then this incident took place in January of 2008, and Star magazine (Via PopCrunch) reported that the pair met at the Beverly Hills Hotel, and Timberlake invited her back to his suite. However, a source claimed that despite being invited to his hotel room, Lohan “insisted he meets her at her house in West Hollywood so they wouldn’t be seen….”

These two were definitely not relationship material though because the source claims Lohan planned to meet up with Timberlake again, but nothing more happened.

Adam Senn Even Got To Meet Her Family

Adam Senn’s name might not be as recognizable as some of the other men on this list, but you will undoubtedly recognize his face because he’s one seriously good-looking guy. Senn, whose modeling credits include a controversial campaign for Gucci, reportedly met Lohan in New York City in December of 2009 during New York Fashion Week.

At the time of their coupling, a source told New York Daily News, “they really hit it off,” and revealed Senn thought Lohan was “a fun girl.”

Things got pretty serious between these two because Lohan even brought Senn to meet her family. The pair attended her sister Ali's 16th birthday together, and apparently, her mother Dina Lohan approved. A source said, "Dina really likes him. She thinks he is 'good for her.'"

She Had A Very Short-Lived Romance With Ryan Adams

In February of 2006, Lindsay Lohan and singer-songwriter, Ryan Adams, were linked— you may know him better for his relationship with Mandy Moore, who he was married to from 2009 to 2016. According to reports at the time, Lohan had a bit of a thing for musicians and was only too happy to have caught Adam's eye.

Not much is known about this relationship, but according to Digital Spy, an anonymous source revealed, "She's spending all her free time with him and stayed at his Greenwich Village apartment in New York almost every night." Yet despite the source’s comments sounding very promising, unfortunately, it wasn’t meant to be.

According to Who’s Dated Who, the coupling was brief, very brief, and they apparently started and ended their relationship in the same month.

Heath Ledger Was The Love Of Her Life, Apparently

It's odd to think of Lindsay Lohan dating Wilmer Valderrama or imagine her hanging out in the same circles as Justin Timberlake, but out of all the men who she is reported to have been romantically linked to over the years, there is only one story that's truly heartbreaking. And that story involves her secret romance with Heath Ledger.

According to Us Weekly, at the time of Ledger’s passing in January of 2008, he and Lohan had been romantically involved. Well, at least according to her mother, Dina. The publication reported on how Radar Online had obtained a recording of Dina telling her ex-husband, Michael Lohan, about the relationship, saying their daughter “was dating Heath..." She added, "I don't know if you know that, but I know cause I would drop her off and they were friends, very, very close."

Then in 2011, a diary which was believed to have been written by Lindsay was obtained by Star magazine, and it described her relationship with Ledger. She wrote, “He was the love of my life.”

Philipp Plein Was A Total Gentleman

The German fashion designer, Philipp Plein, was very briefly linked to Lindsay Lohan in 2011 after she was photographed for his spring campaign. The pair were spotted walking hand-in-hand in Milan looking very cozy, which immediately sparked rumours of a romance, and according to Daily Mail, they were also photographed looking as though they had just shared a kiss.

But according to E! News, there may not have been more to this relationship than friendship. A source close to Lohan told the publication, "Those types of things are not taken as seriously as they are here in the states. Lindsay has many friends. He's a gentleman. He brought her over there and was showing her around town. They went shopping and were just having a good time." But are you convinced?