Anna Nicole Smith was a playboy model who captivated many with her stunning appearance. However, the actor and TV personality was genuinely drawn to a very small number of men, two of whom she eventually married alongside Smith.

According to Who’s Dated Who, Smith had an intriguing dating past that included speculations that he had dated former President Donald Trump. Many people have been enthralled with the gorgeous model’s love life, wondering who would be fortunate enough to be in a relationship with her. But Smith was picky about who she let into her life, and when it came to something as important as marriage, she had certain standards that they had to meet. During an interview with Stina Dabrowski, the “Be Cool” celebrity revealed the qualities she was looking for in a possible spouse. “I love a funny man,” she remarked, “someone very nice, someone very understanding, someone who fell in love with my kid.” They must be quite sensual. The model believed she had finally found the life partner she had been searching for.

Though the Playboy model had multiple romantic relationships prior to her untimely demise in 2007, three stand out in particular: Billy Wayne Smith, J. Howard Marshall II, and Larry Birkhead. Only two of the three guys, nevertheless, truly exchanged vows with Smith.

Anna Nicole Smith was married twice

Anna Nicole Smith thought she found her forever love not once, but twice. According to HollywoodLife, the Playboy model first got married in 1985 to Billy Smith long before she had gained any fame. At the time, they were only 16 and 17 years old respectively. During their marriage, the couple welcomed a baby boy named Daniel Wayne Smith, who died years later due to an accidental drug overdose. Anna Nicole and Billy’s marriage didn’t last long, as they broke up in 1987 and got divorced in 1993.

Before the couple had finalized their divorce, Anna Nicole had already moved on to someone else. While working at a strip club in Texas in 1991, she met billionaire J. Howard Marshall. The two began an affair, but what was even more shocking was that Anna Nicole was 63 years younger than Marshall. The couple got married just a year after she was divorced from her first husband, per CNN.

While many believed the actor had used Marshall for his money, Anna Nicole continuously denied this idea and claimed she was madly in love with Marshall. According to CNN, Anna Nicole told Larry King, “I loved him for so much for what he did for me and my son. I’ve never had love like that before. No one has ever loved me, and done things for me, and respected me and didn’t care about what people said about me.”