Thanks to his brilliant performances in Ace Hunt and Death Illusion, Hollywood movie star Jack Gyllenhaal rose to fame around 2000.
As an A-list actor, Jack has dated many well-known actresses over the years.
These women include Reese Witherspoon and singer Taylor Swift, among others.
<h1 class="pgc-h-arrow-right" > Reese Witherspoon</h1>
From March 2007 to the end of 2009, Jack's date was well-known actress Reese Witherspoon.
Even after the breakup, Jack has been praising the "Legal Lady" movie star.
Reese's current husband is agent Jim Tuss.
<h1 class="pgc-h-arrow-right" > Taylor Swift</h1>
Between 2010 and 2011, Jack's date was the famous singer Taylor Swift.
Fans will definitely remember that during that time they were often tired of being together, but the good times were not long.
Taylor also wrote jack many songs, some of which became hits, such as "We Are Never Ever Ever Getting Back Together" and so on.
<h1 class="pgc-h-arrow-right" > Rachel McAdams</h1>
Rumor has it that in 2014, Jack had dated "Mean Girl" movie star Rachel McAdams.
While neither confirmed the relationship, there were several times when people saw them go out to dinner or go to sports tournaments together.
Of course, they co-produced the sports film Tekken. So maybe they're just filming together.
<h1 class="pgc-h-arrow-right" > Kirsten Dunst</h1>
Another well-known Hollywood star Jack is Kirsten Dunster.
The two dated from 2002 to 2004, and unfortunately, the relationship did not come to fruition.
Although they broke up for various reasons, their acting careers continued to rise.
<h1 class="pgc-h-arrow-right" > Natalie Portman</h1>
In 2006, Natalie had a scandal with Jack.
However, the two have only dated for a short time, seemingly because they realize that the other person is not a type of person.
< h1 class="pgc-h-arrow-right" > Anna Kendrick</h1>
It is said that during the filming of the action thriller "End of Vigilance" in 2011, Anna had a date with Jack.
However, neither of them confirmed the relationship, saying they were just good friends.
<h1 class="pgc-h-arrow-right" > Jenny Lewis</h1>
Jack's first girlfriend was singer-songwriter Jenny Lewis, and the two dated in 2001.
At the time, their careers were just getting started. Some even said that Jenny was actually more famous than Jack.
< h1 class="pgc-h-arrow-right" > Alyssa Miller</h1>
Between 2013 and 2014, Jack dated a well-known model, Alyssa Miller.
The two often went out together, but parted ways a year later.
Now, though, jack seems to prefer model girlfriends.
<h1 class="pgc-h-arrow-right" > Ruth Wilson</h1>
In 2005, during a collaboration on a new Broadway play, Constellations, the two had a scandal.
While some have seen them kissing and holding hands at parties, they claim the two are just colleagues and good friends.
<h1 class="pgc-h-arrow-right" > Jeanne Cadieu</h1>
Jack's current girlfriend is French model Jeanne Cadieu.
They start dating in 2018 and although the two have a 16-year age difference, they are happy together.
Now that their relationship is in its third year, it seems that both value the relationship.