Hollywood star Kevin Costner, known for his leading roles in films and the hit TV series "Yellowstone," is navigating the waters of singlehood with caution after his recent divorce. The 68-year-old actor, who has experienced two high-profile divorces, is reportedly wary of jumping back into the dating scene, especially considering the financial implications of his past marital splits.

Costner's recent legal victory in his divorce from Christine Baumgartner, his wife of 18 years, has been a significant relief. The actor managed to uphold a prenuptial agreement, limiting the financial settlement to just a few million dollars of his estimated $400 million fortune. This outcome was notably different from his first divorce from Cindy Silva, his college sweetheart, who received a staggering $80 million settlement after their split in 1994.

Baumgartner, mother to three of Costner's children, reportedly felt like a single mother while Costner was away filming. Their divorce, unlike his first, was free of any scandalous accusations of infidelity, which had marred his first marriage's end.

In the interim period between his two marriages, Costner was linked to several high-profile figures, including Australian supermodel Elle Macpherson and Bridget Rooney, with whom he shares a son, Liam. However, after these experiences and the financial toll of his divorces, Costner appears to be treading carefully in his newfound single status.

According to sources close to the actor, Costner's past marriages to women who were not wealthy at the time have made him more cautious. "Neither Cindy nor Christine had much money when he married them, so Kevin would feel a lot more confident if a new gal had big bucks of her own!” a friend of Costner's revealed. This sentiment reflects a change in Costner's approach to relationships, where financial security and mutual independence are becoming key considerations.

As Costner embarks on this new chapter in his life, it remains to be seen how he will balance his successful career with his personal life, especially given his apprehensions about entering into another marriage. His experience is a reminder of the complexities that often accompany relationships in the public eye, particularly when significant assets are involved. For now, the acclaimed actor and director seem content to focus on his career and personal growth while keeping a cautious eye on the future of his romantic endeavors.