Jessica Simpson Teases How She Wants Her Date Nights To End Amid 'Rough Road' Of Singleness

Jessica Simpson is thriving amid her separation from her husband of ten years, Eric Johnson. 

The singer announced the end of her marriage to the former NFL player in January, revealing they had been living separately while prioritizing the needs of their three children. However, she is ready to get back in the dating pool and hopefully be intimate with a new man.

Jessica Simpson's comments about her post-separation life follow her spectacular return to the MTV Video Music Awards after nearly two decades.

Simpson got candid about what the future holds as a single woman while celebrating the 20th anniversary of her fashion venture, The Jessica Simpson Collection. When asked what items she would pull from the brand's "2.0" line, the singer said:

"Well, hopefully things will be pulled off. Just kidding! A leopard-print dress, definitely heels, the Aaminas (her strappy platform sandals). I just called to get them in red."

Simpson's playful comment about getting intimate with someone else came months after she announced her separation from Johnson. She told PEOPLE that her collection captured every stage of her life, including her breakup, with pieces for date nights added to the "2.0" line.

Simpson's interest in dating again made waves last month, with The Blast reporting that her ideal method of finding a new man was through her friends. "It's a rough road out there in the dating world. I mean, I'm not getting on the apps yet," she explained.

The media personality noted she would love her friends to set her up with a potential partner rather than meeting people through dating apps. She reportedly met her estranged husband through a mutual friend, and presumably wanted to keep the tradition.

As for her relationship with Johnson, the former couple turned heads in April when they appeared as a united front during a family outing in Carlsbad. Although they reunited for the sake of their three children, sources claimed Simpson and Johnson seemed distant.

Earlier this month, Simpson got fans talking when she mocked a former boyfriend for his cheap gift. The Blast covered the story, sharing that she called out former NFL player Tony Romo during a performance in Pittsburgh.

Simpson was performing at the 2025 Women Who Rock Benefit Concert when she opened up about her awkward reunion with her ex-boyfriend. She claimed Romo contacted her mother out of the blue because he wanted to sell the boat she had gifted him.

The entertainer reportedly gave him a $100,000 speedboat for his 28th birthday in 2009, but her name was still on the papers. Simpson noted she signed over the boat for Romo to sell; however, he repaid her with plastic cups. "I'm like, 'Wow, I'm glad we didn't work out,'" Simpson told the crowd.

Before dating Romo from 2007 to 2009, Simpson was in a relationship with fellow singer John Mayer. The former couple began dating in 2006 and appeared to have a passionate relationship, with Mayer once calling Simpson his "sexual napalm."

Their passionate atmosphere was broken in Simpson's 2020 memoir when she revealed their relationship wasn't as loving as it appeared. She noted they had an on-and-off-again relationship before finally going their separate ways.

Simpson was tied to Maroon 5 frontman Adam Levine before her relationship with Mayer. She sparked infidelity rumors for cheating on her then-husband, Nick Lachey, with the singer, but the speculations were never confirmed.

When she wasn't making waves for her relationships, Simpson made a statement with her beauty. The Blast reported that she stunned fans with her fantastic transformation at MTV's annual Video Music Awards.

She attended the event in a sexy black dress, rocking a sheer fabric with a crisscross design that flaunted Simpson's curves. The outfit showcased hints of skin while offering enough coverage for the singer to slay effortlessly without worries.

The highlight of the night for fans was Simpson's face, which looked more sculpted and toned than her previous features. Her stunning looks had many wondering if she had undergone cosmetic procedures to achieve her wrinkle-free visage.