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The couple, who have a 15-year age difference, made their relationship official on Instagram on Sept. A father of three, Disick posted a photo of their Miami trip together and Richie, too, shared a similar picture.

The two were also seen kissing while out for dinner.

Sadly, Kristen and Rob broke up soon after., where they shared their first kiss as Jackie and Kelso (and Mila’s first kiss ever! Staying friends through the years, the pair only started dating in 2012 after Ashton separated from his then-wife, Demi Moore.

" star began dating the film's director, 22 years older than her, in September 2016 after completing the movie.

The couple split in 2008, then reunited and got engaged in 2010, only to part ways again later that year.

Liz and Dick remarried in 1975, but ended it for good the next year.—although Brad was married to Jennifer Aniston at the time.Donald Trump's daughter certainly had a thing for famous men, judging by the two stars she was previously linked to in her mid-20s. The 35-year-old business mogul briefly dated Grace back in 2006.The owner of her eponymous lifestyle brand had to kiss a few frogs before finding her Prince Charming -- and the list includes "Spiderman" star Topher Grace and U. In fact, Ivanka celebrated her 25th birthday in 2006 alongside the hunky actor at Las Vegas nightclub, Pure.The couple welcomed their first child together, a baby boy on Dec. Speaking about their 46-year age gap, Silver said, “He is a lot of fun. He’s immature in a good way with the wonder of a child. The duo that had an age gap of 23 years got married in February 2015 and their divorce was finalized in August 2016.With 17 years between them, the fashion designer found love with Sarkozy, the half-brother of former French president Nicolas Sarkozy.

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