Clooney dated Pfeiffer, the younger sister of Michelle Pfeiffer, before making movies with both of them: 1989's Red Surf with the former and 1996's One Fine Day with the latter. "Kind of cute, one of Dedee's boyfriends, yeah, OK, nice to meet you...," Michelle said of her first impression of him.

Clooney and the future Mrs. John Travolta lived together, and he gave her a pet pig, Max. After they broke up, Clooney raised Max until his death in 2006.

For 25 years, Balsam had the distinction of being the only woman to get Clooney to settle down. They wed in Las Vegas just months after he split from Preston. "I probably — definitely — wasn't someone who should have been married at that point." Clooney told Vanity Fair later. "I just don't feel like I gave Talia a fair shot." Balsam married John Slattery in 1998 and plays his first wife Mona on Mad Men.

Clooney revealed in Esquire that he once dated Star Trek: The Next Generation's very own security chief Tasha Yar.

Clooney hooked up with the Head of the Class actress after meeting on the set of a commercial. According to Russell, who guest-starred on ER in 1998, Clooney dumped her after she wanted him to put a ring on it. "Don't mention marriage or commitment or babies to George," she said.

The former MTV VJ was Clooney's date to the Emmy Awards in 1995 and they remain close friends. She hung out with him and then-girlfriend Elisabetta Canalis at his Lake Como, Italy, villa in 2010 and plans to give the notorious prankster whoopee cushions as a wedding present. "I have a tradition where I make needlepoint whoopee cushion covers and bring it to his house," she told People. "His beautiful home has several of my needlepoints and when you sit on it, it sounds like a tugboat fart."

After meeting in the City of Lights, where Clooney was filming The Peacemaker, the French law student/waitress followed him back to L.A. If it sounds too good to be true, it is. "She lasted as long as I think she was going to last," he told Esquire. "It was like, 'I don't really think I want to play anymore.'"

Clooney briefly rebounded with the Melrose Place star after splitting from Balitran. Langton later dated Tiger Woods.

Clooney romanced the Two Guys, a Girl and a Pizza Place and Monk star in the spring of 2000, when they were snapped out on motorcycle dates.

Clooney and the British TV personality had an on-again, off-again relationship for five years before finally calling it quits. "We [broke up] three years ago, but I still get asked about it a lot," Snowdon said in 2008. It was also during this time that Clooney was rumored to be dating Renee Zellweger, but both have denied it.

Clooney fell so head over heels for the Canadian waitress that he cast her in a bit part in his directorial debut Confessions of a Dangerous Mind.

Mixing business with pleasure again, Clooney started dating Allen after casting her in Confessions of a Dangerous Mind. They briefly split in 2004 before reuniting and then broke up for good in 2006.

A former Fear Factor winner, Larson was — what else? — a waitress in Las Vegas when she and Clooney embarked on a whirlwind romance that included a motorcycle accident. She was the first of three girlfriends he brought to the Oscars for his last three acting nominations.

The Italian TV personality certainly made the most of her two-year romance with Clooney. Three months after their June 2011 split, she competed on Dancing with the Stars, but was the second person eliminated. She later dated Steve-O and married orthopedic surgeon Brian Perri in Sardinia, Italy, on Sept. 14.

Clooney quickly moved on with the former WWE Diva, but they parted ways two years later over their differing views on marriage and kids. Keibler married entrepreneur Jared Pobre in March 2014 and welcomed a daughter, Ava Grace, in August.

Bachelor no more! Six months after they first stepped out together, Clooney decided that he is the marrying kind and popped the question to the human rights lawyer in April 2014. And he can't stop gushing about her. "I would just like to say to my bride-to-be, Amal, that I love you very much and I can’t wait to be your husband," Clooney said in a speech on Sept. 8.