Tara Reid may have been taken out of a Chicago hotel on a stretcher this past weekend, but her dating history has always made headlines for more than just her acting roles. From her attention-grabbing breakups to notoriously colorful exes, the Sharknado icon's romantic past is packed with jaw-dropping hookups, some questionable choices, and a couple (or more) of names immediately recognizable.The 50-year-old star, a prominent name in the '90s and early 2000s, headlined some of the classic teen flicks, such as American Pie, The Big Lebowski, and Cruel Intentions. Following her incident at the Chicago hotel, her past romances were also revisited.Without further ado, here is Tara Reid's complete relationship history.Steve Burton (1994)Tara Reid briefly dated Steve Burton in 1994. They first met during the set of a series when she was only starting in her career.Steve Burton - Source: GettyDevon Sawa (1998-1999)Reid and Casper icon Devon Sawa dated in 1998 after working together in the teen horror flick, Idle Hands. They called it quits in 1999.Beyond Fest Special Screening Of Sony Pictures' "Heart Eyes" - Source: GettyCarson Daly (2000-2001)Tara Reid and TV host Carson Daly started dating in 2000 after they first met on his show, Total Request Live. The pair rose to become an iconic Y2K couple, and eventually, they got engaged in 2001. Sadly, they broke things off in 2002.43rd GRAMMY Awards - Universal Music Group After Party - Source: GettyTom Brady (2002)Although it was unconfirmed, Reid and NFL superstar Tom Brady reportedly dated after they were spotted together on multiple occasions at the time. Rumors of their romance eventually dissipated as they moved on to different partners.Detroit Lions v Dallas Cowboys - Source: GettyWayne Boich (2003-2004)Tara Reid and entrepreneur Wayne Boice briefly dated in 2002 after meeting at a party in Miami. The pair attended various events and spent time together on Boich's yacht at the time. They broke up the following year.Kyle Boller (2004)The American Pie actress had a brief relationship with Kyle Boller, a former NFL player, in 2004. They first met at a football game and were seen together at various sporting events during the course of their short-lived romance.Sergei Fedorov (2004-2005)In 2004, the actress started dating Sergei Fedorov, a Russian ice hockey player. They broke up a year later.2015 Hockey Hall Of Fame Induction - Press Conference - Source: GettyJulien Jamourne (2008)Reid started dating Julien Jamourne, a fashion designer, in 2008 after meeting through mutual friends. Together, they were seen at various fashion events, showcasing their chemistry. Sadly, they broke up in 2009.Michael Axtmann (2010)Reid dated Michael Axtmann, a German entrepreneur, in early 2010 after first meeting at a party in Los Angeles. Quickly, they got engaged as Axtmann proposed to the actress during a romantic dinner. However, just months after their engagement, they called off the wedding and broke up in April that year.RIM Presents 'Developed In Germany' - Source: GettyZach Kehayov (2011)The actress married Zach Kehayov in 2011 during their Santorini vacation after dating for only two months. However, their union was not legally recognized. Eventually, Reid clarified that she was still single.Erez Eisen (2013-2014)Tara Reid and Israeli musician Erez Eisen began dating in 2013 after first meeting at a music festival. During their relationship, the couple attended various events and showed their shared love for electronic dance music. However, the couple ended their relationship after less than a year.Rock in Rio 2019 - Day 5 - Source: GettyTed Dhanik (2017)The actress dated American business executive Ted Dhanik for a period in 2017, but the exact duration of their relationship was not specified. Eventually, the two moved on to different partners.Premiere For TBS's "Drop The Mic" And "The Joker's Wild" - Arrivals - Source: GettyNathan Montpetit-Howar (2019-2025)Tara Reid was in a long-term relationship with Nathan Montpetit-Howar, co-founder of the sound technology company Phantom. They started dating in September 2019. Sadly, the couple broke up in November 2025, with sources close to the Urban Legend star citing that the relationship had "run its course."Apart from her romantic history, Tara Reid was also rumored to have had flings with Fred Durst (2000), Jason Briggs (2000), JC Chasez (2002), Eminem (2004), Tommy Lee (2005), Giuseppe Cipriani (2008), and Travis Barker (2009).Tara Reid seen disoriented, assisted by paramedics at Chicago hotel in viral clipOn Sunday, Nov. 23, Tara Reid was spotted being escorted by paramedics out of a hotel lobby, according to a video obtained by TMZ. The actress was reportedly dazed and slurring while in a wheelchair. At one point in the now-viral footage, Tara Reid could be heard telling the paramedics:"You don't know who I am. I am famous. I'm an actress."Following the incident, the actress spoke with TMZ to explain what happened while restating that her drink was spiked."So I got to the hotel, I checked in, and then I went downstairs to have a drink and have a cigarette, and I got my drink, and I left it at the bar, and I went outside, smoked a cigarette, and there was a bunch of YouTubers there in the lobby, like everywhere. And they're videotaping stuff and, you know, everything. It was just weird."INFOLIST.com Red Carpet Holiday Extravaganza & Toy Drive For The Children At Shriners Children's Hospital - Source: GettyThe My Boss's Daughter star continued:"And I went back to the bar, and my drink was covered up with a napkin. And I thought, 'That was weird,' cause I never put that over my drink. And then I drank my drink, and without even finishing my drink, I just passed out. And before I knew it, I was in the hospital, eight hours later."During the conversation, the actress expressed how grateful she was that it happened in a public establishment."Like, and there was security there to help me, cause I mean, if this happened at... not a public place, I mean, you could get r***d. You could get... a lot of things could go really, really, really wrong."