One of Stephanie McMahon's first storylines as an on-screen character in WWE was a romance with former Intercontinental Champion Test. On the June 7, 1999, episode of RAW, the latter asked The Billion Dollar Princess out on a date, to which she agreed, signaling the start of their relationship.
After several weeks together, the couple got engaged. However, Stephanie suffered from amnesia ahead of their wedding after accidentally getting hit in the head with a metal trash can thrown by The British Bulldog. The wedding was postponed as The Billion Dollar Princes could not remember her fiance.
The storyline then witnessed Stephanie regaining her memory and proposing to Test inside the ring to confirm their reunion as the wedding went back on. Nevertheless, Triple H crashed the ceremony on the November 29 episode of RAW to reveal that he had married a drugged Stephanie at a drive-thru in Las Vegas.
Despite Stephanie apologizing to Test on the following episode of SmackDown, the latter asked for time to think about what had happened. On the December 11 episode of the blue show, Test sat down with The Billion Dollar Princess to finally end his six-month relationship with her.
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"Steph, I know it's taken me a long time to come to you but it's been a real rough couple [of] days for me to clear my head. I can't imagine what you're going through. And this is really hard, but I think it's best for everybody if we just call the engagement off now," he told Stephanie.
A crying Stephanie then took off her wedding band and gave it back to Test, apologizing to him, saying she never meant for any of that to happen. The former Intercontinental Champion told his ex-fiancee he would always care about her. As the two were about to kiss, they were interrupted by X-Pac.
Stephanie McMahon had another breakup on WWE RAW three years later
Although Stephanie McMahon initially sought to end her marriage to Triple H and asked him to sign an annulment, she later turned on her father, Vince McMahon, and sided with The Game. The two became a power couple in the Stamford-based company for nearly three years before they had a messy breakup on WWE RAW.
After Triple H returned from injury in early 2002, Stephanie claimed she was pregnant as she felt he was about to leave her. The couple then decided to renew their vows in a ceremony on WWE RAW. However, The Game's mother-in-law, Linda McMahon, called him before he went out to the ring to inform him that her daughter was lying to him about her pregnancy.
Instead of a romantic vow renewal ceremony, Triple H betrayed his wife, told her their marriage was over, and took out her father with a Pedigree. Several years later, The Billion Dollar Princess picked that moment as her most memorable one on WWE RAW.