Olivia Wilde Romance Wasn’t Harry Styles’ First Relationship with Massive Age-Gap, Singer Also Dated a Late British TV Presenter When He was Only 17
Many fans were surprised to hear about Harry Styles breaking up with actress Taylor Russell. According to People, the two were first seen together in June 2023. A month later, she was seen attending his Vienna concert. In August 2023, Styles supported Russell at the opening night of her play, The Effect, in London.
Photos showed them getting cozy at a post-show party. And, in September 2023, Styles and Russell were spotted holding hands while on a coffee run in London. But it’s reported that the two had parted their ways, now.
While, the reason for their split is private, it has started discussions about age differences in relationships again. This comes up especially because of Styles’ past relationship with Caroline Flack, a British TV presenter who was 14 years older than him.
Harry Styles’ Short-Lived Romance with Much Older Lady
In 2011, young Harry Styles was in the news for dating Caroline Flack, who was 31-years-old back in the day. Their relationship started well but quickly fell apart once it went public. In her autobiography, Flack wrote they were happy at first but things changed when paparazzi took photos of the 1D member leaving her house. The age difference drew a lot of attention, and the TV presenter faced a lot of harassment.
As she penned in Storm in a C Cup: My Autobiography:
We were both single, we got on well and we had a laugh. It was only when it became public knowledge that things turned sour. At the beginning it was all very playful. He joked about being attracted to older women. It began to go wrong when Harry was pictured coming out of my house one morning. And once that was out, it was open season. After that anyone could say anything. In the street people started shouting at me ‘p*dophile’ and ‘p*rvert.’
The couple ended their relationship in 2012, agreeing to part ways. Flack died of suicide in 2020. Styles never spoke about her death, but as reported by the Independent, he wore a black ribbon at the 2020 BRIT Awards — leading many to think it was a tribute to her.
Harry Styles’ Relationships with Older Women
Harry Styles has dated several celebrities who are 4-5 years older than him, including Emily Atack, Taylor Swift, and Camille Rowe. However, his relationship with Caroline Flack wasn’t the only one with a notable age gap. He has also dated older women like Olivia Wilde, who is 10 years older, and Kimberly Stewart, who is 14 years older.
After dating T-Swizzle, the Adore You singer was seen with Kimberly Stewart. Styles was 19 at the time, and the TV personality was 33. They had dinner with Rod Stewart (her father) and his wife Penny Lancaster (her mother). The next night, both were seen together again at SoHo House. A source told People that they seemed to enjoy each other’s company, and that age “doesn’t really matter” in the Stewart family.
Known for keeping his love life private, the now 30-year-old also found himself in romance rumors with Wilde (who had recently split from her fiancé, Jason Sudeikis) in late 2020.
In January 2021, they were seen holding hands at a wedding. The pair were spotted together throughout the year on vacations and outings. A source told People Magazine that things were getting serious, with the English artist getting to know the In Time star’s children. But, in November 2022, it was reported that they decided to take a break due to busy schedules and different priorities.
