Lindsay Lohan's career was so promising at the start. In 1998, she starred in Disney’s The Parent Trap, playing a set of twins, and was instantly praised as an incredibly talented kid. She went on to star in several other beloved Disney productions - she became a household name over the years. However, as is the case with a lot of former child stars, Lindsay’s name eventually became synonymous with 'trainwreck', 'diva', and 'sad'.

She's one of those celebs who's gotten DUIs - in the past, she partied herself senseless. Hanging with other crazy celebrities, Lindsay was on a downward spiral. After spending some time in rehab, Lindsay seems to have straightened out, for the most part. However, there are several Lindsay moments no one can forget; her romance with That '70s Show ladies' man, Wilmer Valderrama is one of them.

Lindsay and Wilmer had a very short-lived relationship; however, there are some interesting tidbits worth noting. Let’s take a look!

15 First!

Despite being part of the Hollywood scene for several years, Lindsay Lohan never had a high-profile boyfriend before Wilmer Valderrama. He was her first! Considering Lindsay’s stunning looks at the time, it’s hard to believe she never had any other suitors before Wilmer. However, being a celebrity can be time-consuming, so maybe she was just too busy.

14 Short Ride

Although Lindsay and Wilmer looked like a sweet enough couple, their relationship obviously wasn’t made to last. These two barely made it to the one-year mark. Lindsay and Wilmer were both young, famous, and rich. They seemed more concerned with the hottest parties than establishing a solid, healthy relationship that would last decades.

13 Age Gap

Yes, Wilmer was Lindsay’s first high-profile boyfriend—and also seven years her senior! They allegedly started dating when she was 17 years old and he was 24. However, for optics, they announced their relationship once she finally turned 18. Let’s hope that’s just a rumor and Wilmer wasn’t being creepy.

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12 Slowing Down

Lindsay’s and Wilmer’s relationship seemed light enough; they frequented tons of Hollywood events and red carpets. However, these two went through some serious times, as well. Lindsay was hospitalized for exhaustion during their time together and Wilmer actually spent a lot of time visiting her in the hospital.

11 That '70s Show

During their romance, Wilmer helped Lindsay get a part on his hit TV show, That '70s Show. Although Lindsay was definitely a high-profile addition to the show, who fans wanted to see, she didn’t last too long. Due to exhaustion, Lindsay had to exit her role and was replaced by another actress.

10 "Over"

Many may have forgotten that Lindsay Lohan had a singing career! Yes, ladies and gentlemen, Lindsay has two albums under her belt and almost no one remembers any of her music. One of her more emotional songs, “Over,” is rumored to be about her painful, yet mysterious, breakup with Wilmer.

9 All Because Of Ashlee?

One theory explaining Wilmer’s and Lindsay’s breakup is that Wilmer broke up with Lindsay to date Ashlee Simpson. This wouldn’t be too surprising, as Ashlee Simpson was in high demand during the early 2000s...and Wilmer Valderrama was a player. However, there’s no way to be completely sure of this.

8 Full Disclosure

Looks like Wilmer kisses and tells! In an interview with Howard Stern, long after his relationship with Lindsay had ended, Wilmer went into graphic detail about their relationship—even describing her…shaving situation. Unfortunately, Lindsay wasn’t the only victim of Wilmer’s outpouring of information. Several other Hollywood starlets were also mentioned.

7 Secretive Duo

As previously mentioned, rumor has it that Lindsay and Wilmer started dating before Lindsay turned 18 years old. Perhaps this is why the two announced their relationship on Lindsay’s 18th birthday? Oh well, age gaps run rampant in Hollywood, but this age gap was a little shady, to say the least.

6 Mysteries

Despite being a very high-profile couple, Lindsay and Wilmer were also extremely private. To this day, no one truly knows why the two broke up. Of course, there’s a host of possible reasons: their age difference, Lindsay’s personal issues, or Wilmer’s wandering eye. However, the public is still left guessing.

5 Playboy Wilmer

Wilmer Valderrama may have played a weirdo on That 70s Show, but that doesn’t mean he was a loser in real life! During the height of his show’s popularity, Wilmer was a ladies’ man who dated all the popular “It girls”: Mandy Moore, Lindsay Lohan, Ashlee Simpson, and the like!

4 He Moved On

Obviously, Wilmer’s and Lindsay’s relationship wasn’t the love story of the era. They didn’t even have a nickname like “Brangelina” or “Bennifer.” Therefore, Wilmer didn’t have much trouble moving on, with a mind to finding his actual soulmate. Wilmer proposed to Amanda Pacheco on 1 January 2020, and the couple seems incredibly happy.

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3 She Liked Girls, Too

Yes, Lindsay loves guys and dated Wilmer Valderrama. However, that doesn’t mean she only likes guys. Few people remember that Lindsay likes who she likes. A few years after breaking up with Wilmer, Lindsay dated the English DJ, Samantha Ronson. Unfortunately, the two had a very rocky and tumultuous relationship.

2 Lindsay's Forthcoming Low

Thankfully, Wilmer got out of the way before Lindsay experienced what had to be her worst year yet (publicly, at least). It was 2007 when Lindsay began making a host of horrible decisions. Driving under the influence, court trials, drug use, and rehab swirled around her like a bad dream.

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1 She Moved On...Kinda

It seemed like Lindsay met her match in 2016, as she was engaged to the 22-year-old Russian heir, Egor Tarabasov (Lindsay was 30 at the time). However, the two had an explosive fight one night and broke up. It doesn’t really matter, anyway. Lindsay is fabulous in her own right.

NEXT: If You’re Rewatching That '70s Show, Watch Out For These Easter Eggs