9 Celebrity Couples You Definitely Forgot About, Including (No Joke) Betty Draper & Kelso — PHOTOS

I couldn't imagine why anyone in Hollywood would be such a glutton for punishment that they would agree to date another celebrity. With the exception of few famed unions, including some odd celeb pairings you'd never expect, the lifespan of the average hot celebrity couple is something like 23 seconds before one relationship gets pushed out the door in favor of another fling with a different co-star. At the same time, can you blame anyone for dating Orlando Bloom or Angelina Jolie if given the chance? Heartache be damned, they're just two of thousands of insanely attractive celebs who are worth the tears and hours of therapy.

With so many famous relationships to keep track of, it's easy to forget there was life before Ryan Gosling and Eva Mendes — and that both they and countless other celeb couples had some pretty wild and significant relationships in their earlier days. But for every Gisele Bündchen and Leonardo DiCaprio (or Leo and Blake Lively... or Leo and fill-in-the-blank...), there's also a Madonna and Tupac Shakur — a celeb union so confounding you can't be blamed for forgetting it ever existed.

Take a trip down memory lane and see how much these celebrities' dating tastes have evolved (or stayed exactly the same). Here are 11 celebrity couples you totally forgot about or never, in your wildest dreams, would have believed ever dated.

1. Ryan Gosling & Sandra Bullock

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Sandra Bullock and Ryan Gosling met on the set of Murder by Numbers and dated from 2002 until 2003, despite their age difference — she is 16 years older than he is. According to Radar Online, Bullock tries to avoid Gosling when possible because he reportedly broke her heart, which is easy to believe because he breaks the hearts of every woman on Earth on a daily basis.

2. Madonna & Tupac Shakur

In 1994, two years before rapper Tupac Shakur was fatally shot, the pop singer had a fling with him, which she talked about on The Howard Stern Show — over 20 years later! "I was mad at [David Letterman] when I said the f-word a lot," Madonna said in 2015, referring to a '94 appearance on The Late Show. "I was in a weird mood that day. I was dating Tupac Shakur at the time and the thing is he got me all riled up on life in general. So when I went on the show I was feeling very gangsta."

3. Gisele Bündchen & Leonardo DiCaprio

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If ever his fans believed eternal bachelor Leonardo DiCaprio was going to tie the knot and settle down, his long-term relationship with supermodel Gisele Bündchen was the thing that swayed them. From the get-go, DiCaprio has had a specific type, that type being model — he has reportedly dated Naomi Campbell, Bar Rafaeli, and even Adam Levine's ex, Anne V. But his five-year relationship with Anne V was an on-again, off-again heartbreaker that, thankfully, led to the model meeting and marrying Tom Brady and to Leo dating even more models. I call that a happy ending.

4. Rihanna & Shia LaBeouf

Sometimes things aren't meant to be (thank goodness). They might seem like they'd have a little in common (I guess?) but Shia LaBeouf reportedly told Playboy he went on one date with Rihanna, but that “It never got beyond one date. The spark wasn’t there. We weren’t passionate about each other in that way, so we remain friends.”

5. January Jones & Ashton Kutcher

Not only did Mad Men's Betty Draper date That '70s Show's Michael Kelso, she has quite an unflattering story to tell about the time they spent together from 1998 until 2001. Jones told GQ that a guy she dated when she first moved to LA (GQ says it's Kutcher!) was not at all supportive of her career and said she wasn't going to make it. "He was like, 'I don't think you're going to be good at this’. So — f*ck you! He only has nice things to say now — if anything, I should thank him. Because the minute you tell me I can’t do something, that’s when I’m most motivated.” No love lost here, I'm guessing.

6. Mila Kunis & Macaulay Culkin

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Mila Kunis and Macaulay Culkin began dating in 2002 and spent eight years together in a serious, live-in relationship. Proving that you sometimes don't know how you feel about marriage until you meet the person you should marry, Kunis told Blackbook in 2009 that she wasn't interested in settling down with Culkin: "Not to say that I don’t believe in it, but it’s just not something that’s important to me. But I will have children. I’m too selfish to have them now, but when I do, I don’t feel like I need to be married. I need to have a person in my life who will care for me and my children — nothing else." Sounds a lot like Ashton, wouldn't you say?

7. Angelina Jolie & Billy Bob Thornton

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The Angelina Jolie the world knows now — the humanitarian and mother of six who is happily married to Brad Pitt — is not the same Angelina Jolie who made out with Billy Bob Thornton while he told MTV they had sex in a car on their way to a red carpet event back in 2000. The couple was married for three short years, but Jolie filed for divorce shortly after adopting her son Maddox.

8. Mischa Barton & Jamie Dornan

Mischa Barton and Jamie Dornan didn't date for very long — the couple was together for just a short time in 2007. But that was a long enough time for the future Christian Grey to take Barton to an Arcade Fire concert, which is the most adorably 2007 thing you'll hear all day.

9. Lindsay Lohan & Aaron Carter... & Hilary Duff & Aaron Carter

Aww, young love. Yeah, not quite. What should have been a sweet, innocent relationship between Hilary Duff and Aaron Carter turned into a drama-filled relationship between Lindsay Lohan and Carter after he ditched Lizzie McGuire to hook up with Cady Heron way back in the early '00s. It would have been lovely if all three of them left this mess back in the aughts where it belonged. But, in an effort to make everyone uncomfortable, Carter referred to Duff as the "love of my life" as recently as 2014. He even expressed on Twitter how sad he felt about losing his teen love. Duff's response? In an interview with Buzzfeed, after saying she doesn't know Carter anymore, she agreed that his confessions of love were pretty weird.

Agreed. It's as weird as the thought of some of these couples ever existing.

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