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| Filed under: Jake GyllenhaalMatt Dillon

Jake Gyllenhaal was spotted out in New York City embracing his new bachelor status for a guys' night at the Smyth Tribeca Hotel.

Jakey spent the event, which benefited HIV/AIDS charity God's Love We Deliver, chatting and laughing with fellow actor Matt Dillon.

We bet quite a few ladies stopped by to see how Jake was doing, too!

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14 comments to “SIGHting”

  1. 1

    I wanna stop by!!

  2. 2


  3. 3

    Can you please report while he is actually there? Us NYC babes want in!

  4. ap076 says – reply to this


    Good on them for the charity work. I am surprised no comment by the site on two actors so widely rumored to be gay spending time together.

  5. PepeX says – reply to this


    Jake was CELEBRATING - no more lame photo ops with that fugly beard!

  6. 6

    vote number 11 www.jetbluetails.com

  7. 7

    If you notice, there's been tons more pictures of Reese but not Jake. Jake has always been more private. They probably broke up because she wanted to sell her wedding pictures and he didn't! He is a serious actor, she is strictly commercial. One day she is prolly going to have her own TV show. I like Jake. Not only is he seriously hot, he is talented and smart. Too mature for shallow Reese and all her drama.

  8. 8

    This guy makes my gaydar hit the roof. seriously.

  9. 9

    Hmph, I saw this headline at people.com first. Just thought it had a lot of content about blah blah Jake… IsaPerez has elaborated it enough.

  10. 10

    maybe it was a date

  11. 11


  12. 12

    "quite a few"??? every heterosexual female human being will stop by!

  13. 13

    Re: lemonbird

    My take is that her movie fees are dropping and she prolly couldn't afford Jakey any more. She may be looking for a cheaper gigolo.

  14. 14

    Now it is reported that Jakey wants to go back and finish college. He dropped out after his sophomore year. Hmmm…he is now 29. Most Juniors are about 20 so he would be nine years older than the rest of his class. Talk about standing out like a sore thumb. You're too old to go back Jakey. Forget it.