Fraternizing with the 'wrestlers' was forbidden in the McMahon family but almost as soon as the 25 year old (in 2001) Stephanie arrived on the scene in June 1999, she began dating Test. This, of course started a full blown family feud between Stephanie & her brother Shane. Even Shane's long time friends the Mean Street Posse got into the act which didn't give Test much of a break battling his sweethearts brother or a gang of thugs, and sometimes both.
Just when Stephanie and Test were to be married she was injured during the Rebellion PPV in the UK and she lost her memory. Finally in November 1999 the wedding day arrived and just as the minister asked if anyone could show why the two should not be married Triple H stepped onstage. He informed everyone that he had a video they should view first.
The video showed Hunter driving through Las Vegas in a car and pulling into a wedding chapel on the Vegas Strip. As he drove up to a window to get married, we saw his bride to be - a sedated Stephanie McMahon! Triple H said the vows for both himself and Stephanie, put a ring on her finger, and said "I do." They were married! Stephanie had been knocked out by the drink she was offered earlier at her bachelorette party!
The blissful union ended up producing the McMahon-Helmsley Era of the WWF. This pretty much constituted Stephanie and Triple H throwing their weight and big ego's around and generally making most other wrestler's lives miserable. Some of the highlights of her conniving ways during 2000 included calling her mom a bitch and then slapping her in the middle of the ring and illegitimately gaining the WWF Women's Championship (with the aid of Triple H and X-Pac) from Jacqueline while holding onto it for 2-1/2 months without ever defending it. When she finally did defend it against Lita she feigned a knee injury to distract the ref while Kurt delivered an Olympic Slam to Lita. She finally lost the belt to Lita in August 2000 and spent the end of the year plotting with Daddy and getting Linda McMahon committed to a mental hospital and Daddy in full control of the company.
To start off the year 2001 Stephanie violently objected to her Daddy making Trish Stratus his new playtoy. This turned into a full blown feud between the two women during the Royal Rumble where Stephanie attacked Trish. A match was set up for the two at the No Way Out PPV in February, which Stephanie won with the aid of Stephen Regal. As a final insult Vince turned on Trish the next night on Raw and he allowed Stephanie to completely humiliate his former girlfriend by having Stephanie push Trish's head into a horrible bucket of goop and then using the mop on her!
In May 2001 the McMahon-Helmsley Era came to an abrupt halt during a Raw broadcast. The Tag Team Champions Stone Cold Steve Austin and Triple H took on Chris Benoit and Chris Jericho where Triple H severely injured his knee at the end of the match and Jericho covered Austin for the win. For the next few weeks Stephanie's role was unclear and it was rumored that she was going to spend more time writing storylines, but once again the "Billion Dollar Princess" popped up with a new angle that would insure the wrath of Daddy. In July 2001 Stephanie decided she could not be outdone by her brother who had bought the WCW earlier in the year, so it was announced that Stephanie was now the owner of the ECW.
Now brother and sister combined the ECW and WCW into the Alliance, and over the next few months antagonized Dad while Chris Jericho began a hilarious campaign of degrading Stephanie verbally any chance he could get. This included pointing out what everyone had already noticed - Stephanie's breast augmentation. This caused Stephanie to enlist the aid of Rhyno and then Rob Van Dam to shut Y2J's mouth, but neither were really successful, much to the dissatisfaction of the Princess. Also about this time rumors began to crop up about a developing storyline that would have Steph and Triple H getting a divorce, but it never materialized.
In November 2001 rumors appeared that Stephanie and Triple H were now a couple in real life (almost an exact year after Chyna announced she was single). A few weeks later it came out on the Howard Stern show during an interview with Chyna that Stephanie and Triple H were a couple and that Stephanie was the reason they had broken up.
To start off 2002 Stephanie tried to throw her weight around and threaten everyone with the fact that "The Game" was coming back. After a 7 month layoff Triple H returned on the first Raw in January, to the delight of the Madison Square Garden crowd. The following Thursday on Smackdown dropped a complete bombshell. She stated that without her business savvy and brains Triple H never would have been the success he was in the WWF. She also stated that he never would have been Federation Champion nor would he have returned after his injury without her. She said Triple H appreciates her, and with her by his side, he will go on to win the Royal Rumble and become Federation Champion! Stephanie went on to say that Triple H knew that her brains would get him further than any other superstar. She reminded the fans that The Game was back, and she was The Game's wife.
Soon after Triple H's return the Game began to ignore and wind up Steph week by week until one Smackdown during an interveiw with Jim Ross, daddy's little girl came up with an idea which would change Triple H's life forever. The next show came and Triple H walkeded into his and Stephanie's looker room with a big smile upon her face, resting on a chair. Later that night the crowd stood in wait for Stephanie big announcement and then the time come and before the crowds very eyes The Billion Dollar Princess was asking her husband to recite their wedding vows. Momments after Triple H came down to the ring and blasted into Stephanie's ear "NO!!". Stephanie's eyes filled with tears and as The Game was about to leave the ring Stephanie informed him that she was pregnant.This being a big shock to Triple H, he stood in thought. Stephanie still in tears watched bravely as Triple H walked over to her, he took the microphone from her dropped it on the floor and the two celebrated by sharing a long passionate kiss. Throughout the couple of days Triple H was helpful to Stephanie and with that the two would recite their wedding vows the coming raw.
Triple H's dream become reality but how long for? The wedding day came and Stephanie and her husband Triple H talk in the locker room. Momments later Triple H pulls out a beautiful diamond ring and hands it over to the mother of his child, Stephanie. The Billion Dollar Princess was overwhelmed. Later on Stephanie listened to the singers and while doing this her dad Vince walks in, smartly dressed and tells Stephanie that he will be walking his daughter down the ramp. On the overhand HHH sits on the phone to Stephanie's mother Linda who informs him that the whole baby thing was a set up. There was no baby, Triple H laughed confused.Linda tells The Game to open the package which she had sent to him and so he does. As he watches this it shows that Stephanie had hired an actor to play the part of the doctor last Thursday night and by the end of the video, Linda was saying how sorry she was. The time came and Triple H stands in the ring waiting for his bride Stephanie and her father to make an appearance. As soon as their in the ring the two singers begin to sing and The Game stared down at Stephanie, hatred in his eye but whenever Stephanie looked at him a warm smile would be seen on his face.After Stephanie recited her wedding vows it was Triple H's turn and at the very end of his speech he told Stephanie she was nothing but a lying bitch! With that Triple H pedigreed Vince and pushed Stephanie to the floor. Stephanie then crawled over to her father and watched a steaming Triple H walk down the ramp and to his and her concern, their marriage was over!.
The following show Stephanie came down to the ring and discussed her the devorce papers when to her astonishment her well known rival, Y2J Chris Jericho, come down to the ring carrying the WCW title aswell as the WWF title. Stephanie looking confused watched Y2J speak his mind and asked Stephanie if she wanted to make Triple H's life a living hell by them two being friends. Stephanie smirked held out her hand and said that they should make more then just friendship, instead business partners. The Undisputed Champion shook Stephanie's hand and the two annoyed The Game but then Wrestlemanie come. Y2J all fired up for his match against an injured Triple H with Stephanie in his corner. The match ended with Triple H pedigreeing The Billion Dollar Princess and Chris Jericho and with that Stephanie's nightmare had come true as Triple H walked out of Wrestlemania the New Undisputed Champion.