![Celebrity & Entertainment | 50 Photos of Jake Gyllenhaal's Smile Guaranteed to Boost Your Mood | POPSUGAR Celebrity Photo 30 Celebrity & Entertainment | 50 Photos of Jake Gyllenhaal's Smile Guaranteed to Boost Your Mood | POPSUGAR Celebrity Photo 30](https://media1.popsugar-assets.com/files/thumbor/Y2K7FnWsU_I160V9LjhoO-gPGNo/fit-in/2048xorig/filters:format_auto-!!-:strip_icc-!!-/2018/09/07/084/n/44826289/5c64e660b0cdbe67_GettyImages-489476261/i/Jake-Gyllenhaal-Smiling-Pictures.jpg)
Celebrity & Entertainment | 50 Photos of Jake Gyllenhaal's Smile Guaranteed to Boost Your Mood | POPSUGAR Celebrity Photo 30
![FILM DAZE on Twitter: "Jake Gyllenhaal posted up next to a giant bag of bagels while sporting Kermit sneakers...that's it, send tweet. https://t.co/I5upjvEvkS" / Twitter FILM DAZE on Twitter: "Jake Gyllenhaal posted up next to a giant bag of bagels while sporting Kermit sneakers...that's it, send tweet. https://t.co/I5upjvEvkS" / Twitter](https://pbs.twimg.com/media/E2VeHHMXsAAIZ4H.jpg)
FILM DAZE on Twitter: "Jake Gyllenhaal posted up next to a giant bag of bagels while sporting Kermit sneakers...that's it, send tweet. https://t.co/I5upjvEvkS" / Twitter
Spider-Man - December 8, 2018 San Paulo, Brazil - Jacob Batalon, Tom Holland, Jake Gyllenhaal attends Brazil Comic Con for SPIDER-MAN FAR FROM HOME | Facebook
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Jake Gyllenhaal, 38, enjoys romantic night out in New York with girlfriend Jeanne Cadieu, 23 | Daily Mail Online
![Brooks Ravenna 5 Primer Shoe Runner worn by Billy Hope (Jake Gyllenhaal) as seen in Southpaw | Spotern Brooks Ravenna 5 Primer Shoe Runner worn by Billy Hope (Jake Gyllenhaal) as seen in Southpaw | Spotern](https://medias.spotern.com/spots/w640/91/91016-1532336916.jpg)
Brooks Ravenna 5 Primer Shoe Runner worn by Billy Hope (Jake Gyllenhaal) as seen in Southpaw | Spotern
kyra a Twitter: "A Trilogy: jake gyllenhaal w/ a beanie in the subway keanu reeves using a flip phone daniel day-lewis w/ a beanie using a flip phone in the subway https://t.co/xUBM553Zzx" /
![Jake Gyllenhaal and girlfriend Jeanne Cadieu are spotted out separately in New York - Latest Celebrity News Jake Gyllenhaal and girlfriend Jeanne Cadieu are spotted out separately in New York - Latest Celebrity News](https://i0.wp.com/i.dailymail.co.uk/1s/2021/05/08/17/42734576-9557289-image-a-13_1620490520114.jpg?resize=634%2C951&ssl=1)
Jake Gyllenhaal and girlfriend Jeanne Cadieu are spotted out separately in New York - Latest Celebrity News
![Jake Gyllenhaal Keeps It Casual While Heading to a Meeting in LA!: Photo 4037077 | Jake Gyllenhaal Pictures | Just Jared Jake Gyllenhaal Keeps It Casual While Heading to a Meeting in LA!: Photo 4037077 | Jake Gyllenhaal Pictures | Just Jared](https://cdn.justjared.com/wp-content/uploads/2018/02/jake-studio/jake-Gyllenhaal-studio-la-2018-february-01.jpg)