Ashton Kutcher and January Jones

Who: Teen Choice Award-winning actor Ashton Kutcher, 41, and SAG Award-winning actress January Jones, 42.

How They Met: Jones began dating Kutcher in the late ‘90s when she was best known as a model. How, exactly, they met remains undisclosed, but considering the size of the industry pool, we’d assume they ran in similar circles. In 2000, People reported that the actor duo was living together in L.A., but it’s unclear for how long.

Why We Loved Them: I mean, the fashion alone ...

When They Peaked: Their red carpet prom pose should be printed in U.S. History textbooks.

The Breakup: In the words of a post-split Jones, romance “is too hard in this town.” After several years together, the actors parted ways, and there’s a lot of speculation concerning the cause.

In 2009, the Mad Men star told GQ about “the guy I was dating when I first got to L.A.,” explaining that he “was not supportive” of her acting. “He was like, I don’t think you’re going to be good at this. So — f—k 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.”

The article identified said “guy” as Kutcher.

However, 7 years later the plot thickened ... During an appearance on Watch What Happens Live, a caller asked, “Have you ever talked to Ashton Kutcher since he said you couldn't act, and what do you think about his acting skills?” Jones, clearly surprised by the question, responded with, “Ooh, ouch.” She then clarified her comments to GQ, explaining, “I said someone I had dated previously wasn't encouraging of my acting — not that I couldn't. I don't know if that person had ever actually seen me act. But the person who wrote the interview did the math and thought it might be him; I never really said who it was."

When pressed by host Andy Cohen to reveal if said boyfriend was, in fact, Kutcher, she just smiled.

Jones added, “I haven't talked to [Kutcher]. I'm super happy for him and his family, to be political and all that."

In 2019, the release of Kutcher’s ex-wife Demi Moore’s memoir Inside Out revealed another potential source of pressure on the relationship. Moore wrote that Kutcher “was convinced” Jones and Moore’s ex-husband Bruce Willis had had an affair while shooting Bandits in 2000. Moore later ran into Jones and asked her whether Kutcher’s claim was valid. Moore wrote that Jones replied, “Are you serious? I told him a hundred times, I didn’t want to f—k that old man!”

Where They Are Now: After marrying and then divorcing Moore, Kutcher reconnected with his That ‘70s Show co-star Mila Kunis. The couple, who wed in 2015, share daughter Wyatt, 5, and son Dimitri, 3.

VIDEO: Ashton Kutcher and Mila Kunis's Cutest Couple Moments

Kutcher has starred in Netflix’s The Ranch since 2016. The second-half of the show’s fourth season airs on Friday, Jan. 24.

Jones welcomed a son named Xander in 2011. She was most recently linked to a friend of Armie Hammer’s named Nick Delli Santi.

Despite a ~ certain ~ boyfriend’s lack of encouragement, Jones has enjoyed a fruitful acting career. She currently stars in Netflix Original series Spinning Out.

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