10 Of The Hottest Women Ryan Reynolds Has Been With

For a Hollywood A-lister like Ryan Reynolds, his dating history is rather tame compared to that of other leading men (we’re looking at you, Leo). Deadpool - er, Ryan Reynolds - seems to be a fan of love and likes to take his women to the altar as soon as possible. After all, he does have a few engagements and multiple marriages under his belt. 3 engagements and 2 weddings in the span of eight years, in fact. He must be superhuman. On second thought, “serial husband” might be a more apt description here.

We can’t narrow down Ryan's “type” because his dating history includes anything from the likes of Alanis Morissette to dream girl Scarlett Johansson. He has dated women ten years younger than him and ten years older. He does not discriminate. He has definitely had a few high-profile romances in his time as well. He may have even taken a certain teenage witch with a cat named Salem back to his hotel room. He’s even hooked up with Wilma Flintstone, too. Because, why not?


10 Traylor Howard


Ryan Reynolds had a knack for landing cougars - he must be quite a charmer. One such lady was Traylor Howard, who is best known for her roles as Sharon Carter in the TV series Two Guys and a Girl and as Natalie Teeger on Monk. She was ten years older than Reynold’s (they were 22 and 32 at the time they started dating), but that didn’t seem to affect the relationship, which lasted for a good ten months or so back in 1998, even though he was basically a child. At the time, she was at the height of her career for Boston Common and Two Guys, a Girl and a Pizza Place. She is now married and has two children.

9 Alanis Morissette


Ryan Reynold’s relationship with Alanis Morissette was one of his longest, dating all the way back to 2002 (no pun intended). Alanis said, "We have the perfect combination of compatibility and incompatibility that makes the relationship very passionate." The relationship lasted 5 years, which included a three-year engagement. Naturally, Morissette wrote an album (Flavours of Entanglement) about the break-up and the song “Torch” was specifically written about him. Their breakup announcement included a statement about how they are still “friends” (not really), but no other reasons were given. Alanis is now away from the spotlight and happily married. Her second child is on the way.

8 Kristen Johnston

Who wouldn’t want to take Wilma Flintstone to bed? Kristen Johnston was another cougar (nine years his senior) that Reynolds managed to catch, despite the fact that she was at the height of her career in her hit show 3rd Rock from the Sun, and he was relatively unknown. The relationship only lasted five months before they called it quits back in 1999. He was a young 23 years of age while she was 32. During their brief romance, the two did manage to attend a red carpet event together, a reminder to Johnston of what could have been. She is currently living the single life.

7 Sandra Bullock


Sandra Bullock is a hot commodity in Hollywood (and also one of their highest paid actors - who knew?). She has previously dated the likes of Ryan Gosling and Matthew McConaughey. A few years ago, Ryan Reynolds was linked to Sandra Bullock, who was reportedly one of his many rebounds after his divorce from Scarlett Johansson. However, Bullock said that they were not “romantically involved” and were “just friends.” In an interesting turn of events, Scarlett Johansson reportedly gave her stamp of approval to the new couple. A source said that she liked and respected Bullock a lot. She also said she knew how much Reynolds wanted to be a dad and how much Bullock valued motherhood. 

6 Melissa Joan Hart

A Sabrina the Teenage Witch and Deadpool romance seems like an unusual pairing, but nevertheless, the hook up was detailed in Melissa Joan Hart’s book. Apparently, the two met on the set of the Sabrina the Teenage Witch TV movie. On the last day of filming, Reynolds gifted Hart with a watch, which apparently was just the ticket to allow him to take her back to bed (er, the hotel room) where the two “made out.” Rather tame, but what did you expect from a teenage witch? On the event, Melissa Joan Hart had this to say: "I remember that his lips were pretty wonderful, plus he has these big hands and shoulders that completely swallowed my petite frame", she admitted. "It was a terrific distraction from how strongly he smelled of hair product."

5 Rachael Leigh Cook


The two started dating when Ryan Reynolds wasn’t quite yet a household name, back in the early 2000s. Cook, however, an American actress, was known at the time for her roles in She’s All That and Josie and the Pussycats. The two lasted for an entire year, although there aren’t many pictures of the couple save for a red carpet event. Not much is known about the reason for their breakup, but apparently he was a sweetheart, in one instance he secretly followed her to London to surprise her on set at one point. Rachael Leigh Cook has dated a number of other Hollywood actors, including Colin Hanks. However, she has now settled down and is married with children.

4 Agnes Fischer


After Ryan Reynold’s divorce from Scarlett Johansson in late 2010, 2011 became a big year in the lady department. One such conquest was Agnes Fischer, a low-profile, German model, who Reynold’s reportedly hooked up with on the set of Safe House. Agnes Fischer was his “official” rebound (he had many after his divorce from Johansson). In fact, they started getting cozy only two months after the split was officially announced. However, Reynolds wasn’t alone in his rebounding as Scarlett Johansson was reportedly getting close to Sean Penn around the same time.


3 Charlize Theron


The two had a brief summer fling. They apparently had known each other for quite some time since they were neighbours, and always knew that there was a spark. However, Theron might more aptly be described as one of Reynold’s (many) rebounds, as he started dating her after he split from his wife, Scarlett Johansson. The two dated in “secrecy” for several months. The relationship was probably doomed from the beginning given that it wasn’t only Reynolds who had just gotten out of a long-time relationship. However, one source claimed that the reason for the break-up was due to the fact that Reynolds was only looking for something “casual” (we all know how that ends) while Theron wanted to settle down. Apparently she didn’t take it well when he ended things, either.

2 Blake Lively

Blake Lively is Ryan Reynolds current wife and 11 years his junior. The two always appear to be very happy when photographed for various events and have inspired multiple “relationship goals” articles in their honor. The two met on the set of Green Lantern in early 2010. While they didn’t start dating until late 2011, things took off quickly after that: it only took them a year or so to officially tie the knot (and they didn't even announce their engagement). We can’t blame Ryan Reynolds for wanting to tie that down, though. The couple wed in September of 2012 and welcomed a daughter, James, in 2014.

1 Scarlett Johansson


Coming in at the number one spot is no other than Ryan Reynold’s former wife. It took even less time for Ryan Reynolds to put her on lock down (again, we can’t disagree with the man on this one). They started dating in 2007 and by May 2008, they were engaged. Four months later they were married. However, the relationship ended two years later. They were quiet about the reasons for their split, but one insider said it was due to distance, which made Johansson unhappy. However, Johansson might have hinted at the true reason for the break-up, which seemed to have something to do with competitiveness. She said: “Acting is a very strange world to be co-existing in. It’s very volatile,” she revealed to the magazine. “There’s always going to be the more successful person. It’s related to rejection. Because actors, if they’re not having success, connect it directly to unpopularity — to the fact that nobody wants them. 


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