Inside Jerry O'Connell's Dating History — Including His Wife Rebecca Romijn and the Star Who Dumped Him After One Date

Jerry O'Connell's dating history has been quite the roller-coaster ride.

The 52-year-old actor went through breakups before meeting his wife, Rebecca Romijn, before eventually marrying her in 2007. They welcomed twin daughters, Charlie Tamara Tulip and Dolly Rebecca Rose, in 2008.

During their joint appearance on Live with Kelly and Mark on May 8, the Scream 2 actor joked he has "turned into [his] mother" while offering his daughters dating advice.

"I sit down with them and I say, 'Girls, you gotta play the field. You can't just go out with one!'" he said. "I see their friends who are in relationships and they don't have fun anymore."

Here's a look back at O'Connell's dating history.

O'Connell and Sarah Michelle Gellar fueled romance rumors after they attended the 1998 Emmys together — though the actress was "one and done" after just one date.

"We were very young, we were kids," the Stand by Me actor told Kelly Ripa on the "Let's Talk Off Camera" podcast.

He noted that Gellar "needed a date to the Emmys," but the Buffy the Vampire Slayer actress "dumped [his] a--."

"Sarah Michelle took one look at me and was like, 'I got to get away from this drunk,'" O'Connell joked, adding, "Oh my gosh. She was like one and done. Literally, like one date. She was like, 'Well, that was fun.'"

O'Connell and Estella Warren co-starred as lead actors in the 2003 film Kangaroo Jack. Their romance was short-lived, with the pair calling it quits after a few months of dating.

Reports said they remained amicable after the split.

In her memoir Melissa Explains It All, Melissa Joan Hart wrote about her brief encounter with O'Connell — her former classmate — at the Kentucky Derby in 2002.

"Jerry hardly showed me any attention when we were at school or bumping into each other around Manhattan, but that night, he followed me around like a puppy dog," she recalled. "If experience taught me anything, it's that charismatic flirts are rarely boyfriend material—and Jerry sure thought a lot of his own charms."

Hart later admitted, "I also wanted to give him a taste of his own standoffish medicine, since he pretended to barely notice me for four years even though we saw each other all the time."

She ended things O'Connell upon meeting her future husband, Mark Wilkerson.

O'Connell began dating Giuliana Rancic in the early 2000s after they met at the W Hotel in Santiago. They called it quits after two years together.

Twenty-two years later, the Joe's Apartment star looked back at their relationship on the "Let's Talk Off Camera" podcast, admitting he was a "terrible" boyfriend to Rancic.

Following his podcast appearance, Rancic shared a vacation video on Instagram in which she called O'Connell's memory "just a little fuzzy."

"So I'm on vacation, my email's been blowing up with like People magazine, all wanting a comment. I'm like, I could give two sentences, like, 'Blah, blah, blah, I wish him all the best,' or I could just take a deep dive and make it a 40-minute podcast," she teased in the July 23 update. "So tune in next week, 'Bill and Giuliana: The Podcast,' and Jerry – you are so invited."

As promised, she addressed O'Connell's comments on the July 29 episode of the podcast, accusing him of "downplaying" their year-long romance.

Rancic said, "For a year and a half — except for the one breakup — we were together 24/7 every day, every night. You could listen to his interview and think maybe this was an easy relationship, he was dating a bunch of girls, but no. It was a real relationship."

She then called seeing photos of O'Connell and Spice Girls member Geri Halliwell holding hands in London the "most shocking moment" of her life.

"I walked into a voiceover booth and fell to the ground, crying hysterically. It was awful. So upsetting and so devastating," the TV personality added.

After confronting O'Connell about the photos, Rancic said his response left her to "pick up the pieces" of their relationship. But when the Jerry Maguire star's romance with Halliwell fell apart one year later, he reportedly showed up at Rancic's apartment building in tears.

"I am so sorry. I made the biggest mistake of my life. I don't know what I was thinking," she quoted O'Connell as saying. "Please take me back. You're the love of my life."

O'Connell was still dating Rancic when he reportedly had a brief fling with Ginger Spice while filming a movie in London in 2003.

Neither O'Connell nor Halliwell ever publicly commented on the cheating claims.

After several breakups and flings, O'Connell found love with Romijn, whom he met at a Maxim Hot 100 party in Las Vegas on June 12, 2004.

"I remember thinking, 'Wow. This girl is really beautiful and funny,'" he told People in 2017. "I talked to her the whole party. We clicked. We clicked the first time we met. Obviously, she was married [to John Stamos], and I know shenanigans go on, but no shenanigans happened. But we clicked. Day one, we clicked."

They began dating in August 2004 and got engaged in September 2005.

In July 2007, O'Connell and Romijn exchanged vows in an intimate ceremony in Calabasas, Calif., after nearly three years of dating. They welcomed their twin daughters on December 28, 2008.