“American Horror Story” actress Sarah Paulson stated in a 2016 interview that “My choices in romantic partners have not been conventional.” Having a very colorful dating history, Sarah was in a relationship with actress Cherry Jones, who was eighteen years her senior, for five years before meeting her current partner, Holland Taylor who is a full thirty-two years older than her.
Sarah met Holland while still in a relationship with Cherry but stated that Holland was “the most exquisitely beautiful woman” she had ever seen. Speculation about their split first began when Jones made no mention of Paulson during an acceptance speech at the 2020 Emmys. A few months later, the couple announced they were no longer together.
Teddy Geiger & Emily Hampshire
Songwriter Teddy Geiger started dating "Schitt’s Creek" actress Emily Hampshire in 2018, a year after coming out as a trans woman. They had been dating for just a few months when Emily bought a heart-shaped diamond and proposed. It was sudden but both of them seemed excited.
Everyone’s Instagram was constantly updated with the pair’s romance as they consistently posted very public sweet nothings. Sadly, this turned into a very unsweet nothing as the couple called it quits less than a year after getting engaged. Both Teddy and Emily refused to share any details around the breakup and have seemingly moved on with their lives.
Anderson Cooper & Benjamin Maisani
This has to be the most curious breakup story in the history of breakups. Famed journalist Anderson Cooper dated French hospitality magnate Benjamin Maisani for a total of nine years before throwing in their relationship towel. The couple was careful about keeping their relationship private since too much publicity could get out of hand.
One of the reasons they broke up, claims Anderson, was that Benjamin was uncertain about having children. After the breakup, Anderson adopted his son Wyatt and asked his ex to co-parent. One would think that this would end in the pair rekindling their relationship but no – they remain separated but fathers to Wyatt. They had broken up as boyfriends but were committed to being a family together.
Lindsay Lohan & Samantha Ronson
Most of the newly anointed citizens of Splitsville have been pretty civil, but we have an example of the opposite in the form of the very tumultuous relationship and breakup between actress Lindsay Lohan and British musician Samantha Ronson. It started with them flirting and rumors about them dating which they categorically denied. Apparently the two were also fighting and not getting along, which they denied again.
After months of the same pattern on rinse and repeat, a gossip column finally broke the news that the couple had broken up. Lindsay ultimately admitted that “two toxic people cannot be together” when discussing the dissolution of her relationship with Samantha. What didn’t help was the incessant interference in her and Samantha’s private life. Today, Lindsay simply states that she and Samantha were “friends more than anything.” Yikes!
Ruby Rose & Phoebe Dahl
As tragic as each of these breakups has been, what is encouraging is that they have all ended on good notes. This rings true for the 2015 split between Ruby Rose and Phoebe Dahl. Engaged to be married, it seemed that the future was certain for the power couple. They got engaged in 2014 after Ruby pulled off the most unique proposal.
She broke into Phoebe’s house at 5 am with flowers and got down on one knee. Phoebe thought it was a prank. It was a proposal story for the ages. The downfall occurred when Ruby’s meteoric rise in the acting world placed a heavy burden on the couple’s quality time. Impossibly endearing, both Ruby and Phoebe expressed their admiration for each other on social media as they parted ways.