Former NFL star Tom Brady is rumored to be dating "Legally Blonde" actress Reese Witherspoon. It comes a few days after Brady was reported to be back in the dating game.

Before rumors that Witherspoon was dating Brady surfaced, the actress had dated several A-List Hollywood celebrities and had her fair share of bad breakups.

5 Men Reese Witherspoon Dated Before Tom Brady Dating Rumors

Reese Witherspoon is mainly known to have dated five men. She has been married twice and divorced them both. One of them was her longest relationship to date. Here are the men that Witherspoon has dated over the years.

Jim Toth

Her most recent relationship was the most significant and probably the longest. Reese Witherspoon and actor-producer Jim Toth started dating in 2010 before finally tying the knot in 2011. Their son, Tennessee, was born in 2012.

The former couple's marriage lasted over a decade, much like the same with Tom Brady and Brazilian supermodel Gisele Bundchen.

Witherspoon and Toth ended their marriage only this month, but the divorce seems amicable, and they are prioritizing their son even though they have already split up.

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Jake Gyllenhaal

According to Us Weekly, Reese Witherspoon and "Brokeback Mountain" actor Jake Gyllenhaal started dating in 2006 when they worked together in the movie, "Rendition." Much like her breakup with Jim Toth, there was not much drama in their breakup as the couple went their separate ways in 2009. "No one cheated," a source told Us Weekly.

Ryan Phillippe

Reese Witherspoon's other most significant relationship was with her "Cruel Intentions" co-star Ryan Phillippe. They met on her 21st birthday in 1997 and started dating two years later. The two eventually got engaged and married before welcoming their daughter Ava and their son Deacon.

Rumors said Phillippe cheated on the actress with Abbie Cornish. However, Cornish denied that she and Phillippe were dating while he was still married to Witherspoon. They finalized their divorce in 2008 though they both co-parented their children.

Jeremy Sisto

Reese Witherspoon also dated "Clueless" star Jeremy Sisto, and the two were well known as a teeny bopper couple. However, years later, the actor admitted that keeping the relationship was hard as they had a long-distance relationship. The two met on the set of "Desperate Choices: To Save My Child" as teens and started dating soon after.

Chris O'Donnell

Much like Tom Brady, this one only came from rumors and was never confirmed true. But if indeed true, they started dating when she was still 16.

The then-teen Reese Witherspoon was seen accompanying Chris O'Donnell in a tribute for Al Pacino in February 1993. That sparked rumors that they were dating, though it raised a few eyebrows as the actor was 22 then. O'Donnell's rep later confirmed that they were just friends.

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Written by: Rick Martin

WATCH: Reese Witherspoon and Jim Toth SPLIT - From Entertainment Tonight