Prior to working together on the set of Seven, Gwyneth had met Brad Pitt briefly through friends. Brad had been impressed with Gwyneth as an actress after viewing her reading for Legends of the Fall. Although she was not cast for that film with Brad, she was cast as his wife in Seven.

   "Of course, I thought he was very handsome from movies- you know, the way people are. But I also thought, Oh, he'll just be one of those young Movie Star Boys. But he's not. He's a really good person. And I knew it that first day on the set. And then I got nervous." ~ Gwyneth

Gwyneth was dating something else at the time, but not for long. She broke up with musician Donovan Leitch in order to date 30 year old Brad Pitt. At the time, Gwyneth was only 22. Their differences in age did not bother Gwyneth who said,

   "I am properly in love for the first time in my life, and I do not care if my former boyfriends read this."

  Gwyneth was immediately surrounded by publicity as Brad Pitt's new girlfriend. Meanwhile her career was taking off as she was casted as the leading lady in Emma. Since the two lovers had agreed never to spend more than two weeks apart, Brad came along for the trip to England. Later when Brad was filming Seven Years in Tibet, Gwyneth followed him to Argentina.  The on-set physician commented that,

   "They are like adolescents in love, feeding each other, kissing, doing things that people who are madly in love do. As soon as Gwyneth would arrive on the set, Brad would rush off and give her a big hug."

Sometimes when Brad was not on locations for one of Gwyneth's films, she could often be seen drinking from a mug with Brad's picture on the side. She was always anxious for his visits.

   In 1996, Brad was nominated for a Golden Globe for Best Supporting Actor in 12 Monkeys which he won. During his acceptance speech he publicly confessed his feelings for Gwyneth.

  "My angel, the love of my life." ~ Brad

  

"We hang out alone, read papers, have coffee, watch Unsolved Mysteries, or have friends over for dinner and laugh and play Pictionary."
~ Gwyneth

  "He thinks I'm pretty good, you know? He always says, 'You're an amazing woman.' Another thing he always says- oh gosh this is so incredibly embarrassing, but another thing he always says is, 'My girl's got class.' " ~ Gwyneth

In late 1996, Brad asked Gwyneth to marry him and she accepted. For the first time, Brad took Gwyneth to his home in Springfield to meet his parents. They celebrated the engagement with his family at a local Red Lobster. Her engagement ring was a band with four diamonds--one large and three tiny stones-- chosen by Brad.

   On June 16, 1997, Brad's publicit announced that Hollywood's golden couple had called an abrupt end to their 2 1/2 year romance.

   "It's a real relationship with real problems. This is not about any third party. This is absolutely between the two of them."

   The breakup devastated both stars. Gwyneth moved in with her good friend actress Winona Ryder to recover while Pitt went to Rhode Island to give a lifeless portrayal in the film Meet Joe Black.

    Since the breakup, neither star directly speaks about the reasons behind the split. Many speculations have been suggested but the public will never know the true reason. Gwyneth refuses to even refer to Brad by his name, only by  'him.'

Quotes taken from People Profiles, People, Who, and US Magazine.