Gyllenhaal dannede par med skuespilleren [[Kirsten Dunst]] i næsten to år, efter de indledte et forhold i 2002.<ref>{{cite news|title=Gyllenhaal, Dunst call it quits |work=USA Today |url=http://www.usatoday.com/life/people/2004-07-20-celeb-couples_x.htm |access-date=22. august 2010 |first1=Karen |last1=Thomas |date=20. juli 2004}}</ref> Han har senere dannet par med ''Rendition''-medskuespiller [[Reese Witherspoon]] fra omkring 2007 til 2009.<ref>{{cite web| title=Reese Witherspoon & Jake Gyllenhaal Get Close |work=[[People (magazine)|People]] |date=5. april 2008 |url=http://www.people.com/people/article/0,,20033710,00.html|access-date=19. november 2008}}</ref><ref>{{cite web |title=Reese Witherspoon On Kids, Jake, And Working With Vince Vaughn |work=Huffington Post |location=USA |date=14. oktober 2008|url=http://www.huffingtonpost.com/2008/10/14/reese-witherspoon-on-kids_n_134648.html |access-date=19. november 2008}}</ref><ref>{{cite web |first=Ulrica |last=Wihlborg |author2 = Stephen M. Silverman |title=Reps Claim Jake and Reese Are Still Together |url=http://www.people.com/people/article/0,,20323262,00.html |date=29. november 2009 |access-date=30. november 2009|work=[[People (magazine)|People]]}}</ref><ref>{{cite news |title=Reese Leaves Jake; "It Broke His Heart" |url=http://www.usmagazine.com/celebritynews/news/reese-leaves-jake-it-broke-his-heart-20091612 |work=[[Us Weekly]] |date=16. december 2009 |access-date=6. marts 2010}}</ref> Han har desuden dannet par med singer-songwriteren [[Taylor Swift]] fra oktober 2010 til januar 2011.<ref>{{cite web|last=Hammel|first=Sara|title=Taylor Swift & Jake Gyllenhaal Share a 'Friendly' Brunch in Brooklyn|url=http://www.people.com/people/article/0,,20436748,00.html|work=People|access-date=6. marts 2012|date=25. oktober 2010}}</ref><ref>{{cite web|last=Hammel|first=Sara|title=Taylor Swift & Jake Gyllenhaal Break Up: Source|url=http://www.people.com/people/article/0,,20454920,00.html|work=People|access-date=6. marts 2012|date=4. januar 2011}}</ref><ref>{{cite web|last=West|first=Kay|title=Taylor Swift & Jake Gyllenhaal: Back Together Again?|url=http://www.people.com/people/article/0,,20459183,00.html|work=People|access-date=6. marts 2012|date=20. januar 2011}}</ref>
Levende_personer