Harry Styles, the British pop sensation known for his chart-topping hits and high-profile romances, has reportedly set his sights on another iconic figure: Shania Twain. Despite Twain's content and longstanding marriage, sources reveal Styles' admiration and efforts to work closely with the legendary singer, sparking rumors of a potential romantic bond.

Styles, 29, has a well-documented history of relationships with older women. His past romances include a brief affair with television presenter Caroline Flack when he was just 17 and she was 31, and a more recent two-year relationship with actress Olivia Wilde, who is ten years his senior. Following his breakup with actress Taylor Russell in May, after a 14-month relationship, Styles has reportedly turned his attention to Twain, 57.

According to Heat World, the "As It Was" singer has been "flirting" with Twain, an A-list singer he has idolized since his youth. Over the weekend, Twain delivered a stunning performance at Glastonbury, reaffirming her legendary status in the music industry. Although Styles did not attend the event, he made sure to watch her performance, further fueling his admiration for the country pop star.

Sources close to Styles reveal that he has openly acknowledged Twain's influence on his career and is now keen to express his gratitude and admiration. The two artists have shared the stage in the past, and Styles is reportedly making every effort to collaborate with Twain in the future. Despite the age difference and her marital status, Styles' admiration for Twain has led to speculation about a possible romantic connection.

Twain, who is married to French executive Frédéric Thiébaud, 53, for 13 years, reportedly feels flattered by Styles' attention. An insider noted, "Twain is genuinely honored by Styles' admiration and is eager to work together again. However, she emphasizes that she may be among the rare few women who prefer to keep her relationship with the former One Direction member strictly professional."

Styles' fascination with Twain is not solely based on her musical talents. The insider added, "Harry is deeply in awe of Shania. He respects her marriage but can't help but flirt with her. Twain finds Styles to be a lovely and talented young man who deserves all the success he's had."

Their connection goes beyond mutual admiration. Sources indicate that Styles and Twain have engaged in deep conversations about music, personal style, and life. They reportedly exchange career guidance and share a profound understanding of their respective crafts.

Styles has been vocal about his admiration for Twain, describing her as beautiful and kind-hearted, and expressing a desire to meet someone similar. However, despite his evident admiration, the chances of a romantic bond developing between them appear slim. Twain views the "Watermelon Sugar" singer more as a close friend than a potential romantic partner, especially given that Styles is closer in age to her son, Eja, 22, from her previous marriage to music producer Robert John Lange.

"Twain doesn't see Styles as anything more than a sweet kid," the insider continued. "But Styles isn't shy about throwing out the compliments. She does look half her age, and Harry has always had a thing for older women, so it's not really a big shock he's still crushing on her. She's a babe!"

While the prospect of a romantic relationship between Styles and Twain remains speculative, their professional and personal rapport is undeniable. As both artists continue to navigate their successful careers, the dynamic between them will undoubtedly be one to watch.