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Trouble Converting Friends To Dates

[Blind Gossip] This actor became very famous as a child film star. He’s a man now, and he doesn’t always get recognized.

Although he has never stopped working, people are sometimes a little shocked when they meet him because he looks so different.

There was a rumor that he has a serious girlfriend. True?

No, and it bothers him that he has trouble converting friends to dates. Look, he is aware that he’s not as cute as he was when he was a kid, but he really is the nicest guy. He’d like to date more. He’s asked his sister to help him find someone.

Awww. That’s sweet. By the way, his sister is an actor, too.

Similar: Dating Across Lines

Actor:

[Optional] Do you think he’s still cute?

Reader Interactions

Comments

  1. Haley Joel Osmont.

    Looks cant always be helped, but he grew up to be quite unfortunate looking. :\

    • It’s like his facial features stayed the same size while everything around them grew. He seems nice, though.

    • Anthony Michael Hall turned out handsome, but from many accounts, he did not turn out to be a very nice guy.

      I like the Haley Joel Osment guess.

    • Actually I think things were the opposite for Anthony. He was kind of a geeky teen but grew up to be really good looking. I enjoying watching him on The Dead Zone

  8. Haley Joel Osment.

    And yes, he’s a totally lovely guy. I crewed on something he was in. An absolute darling.

  9. Haley Joel Osment? His sister is Emily Osment from Hannah Montana (and probably more recent things).

  14. Actor: Hayley Joel Osment

    The sister mentioned is likely his actor sis Emily Osment. I’ve heard him on podcasts and he seems like a genuinely nice dude. I wish him the best in the dating pool.

  21. Haley Joel Osment. He definitely looks different than when he was a kid, but he’s not bad. It seems hard to believe he’s not having much luck, though. Maybe he’s too nice and/or only interested in women who aren’t interested in him. It might help if he broadens his horizon so to speak.

  22. Hayley Joel Osment
    He doesn’t look THAT different and he seems to be picking interesting projects, he just needs to find some girl who isn’t completely shocked that a human being aged.

  23. Haley Joel Osment… met him randomly once in New York. Great guy, very gracious when people figured out who he was. I’m sure there is someone out there for him.

  24. Haley Joel Osment – his sister is an actress (famous for the Pepsi commerical when she was a kid). He looks like the dude in the pic. Balding with a gut…

    • I think you’re thinking of Jessie Eisenberg’s little sister, the one with the dark curly hair and giant dimples?

  28. Joel Osment. Sister is Emily Osment. He’s merely a rounder and beard-ier version of his young self.

  31. Haley Joel Osment
    (sister Emily Osment)
    He’s no greek god but that doesn’t mean he doesn’t deserve to be happy or loved. Look at Patton Oswalt, Danny DeVito, Mark Anthony, Prince… Haha
    He looks cute as in nice and kind, bearded teddy bear guy. He should look for a normal loving girl outside the industry, definitely NOT the Hollywood type.

  32. Haley Joel Osment. His sister is actress Emily Osment.

    I’m kind of shocked how homely he became as an adult.

  35. H.J: Osment? He was so cute as child and so good actor. He is not your typical Hollywood hottie but I wish he would work more in better roles. I bit worried after the last Spacey scandal, I hope he never was his victim. They filmed Pay It Forward together.

  37. Haley Joel Osment?

    Optional: Whenever I see photos of him he’s always smiling and seems like he’s enjoying life. That should be attractive to women.

  44. Haley Joel Osment went from cute kid to corpulent adult and if I’m going by the picture as a clue, that’s my pick. His actress sister is Emily Osment.

  48. Haley Joel Osment

    Saw him on CPW in NYC last year and he was dressed like a chunky middleaged preppy guy from Rhode Island. He’s cute and just wants to be adored (don’t we all!?!) poor guy, his sister Emily is a stunner.

    • Changing my answer to Haley Joel Osment. The poor guy lost his cuteness when he hit adulthood

  54. Haley Joel Osment and Emily Osment? Jason Bateman has a sister Justine who is/was an actress, but he doesn’t look that much different from his younger days.

  67. Awww, is this Haley Joel Osment? He kind of fell off the radar.

    I don’t know if he’s necessarily “cute” any more, but if he’s turned out to be a nice guy, I wish him well in his search.

  68. Haley Joel Osment is still cute as a button. It’s a shame he’s so short; that’s the biggest drawback I see to him finding dates in this looks-obsessed world.

  69. Haley joel osment. His head grew but his face remained sort of small in comparison. However glad to hear he is still having a career and has grown into a good man despite the toxic hollywood environment.

  71. Haley Joel Osment?
    After seeing him on Silicon Valley last season, he sort of resembles the man in the photo. And his sister is an actress. This makes me sad. He seems like a good guy!

  77. Haley Joel Osment. He’s not really the athletic type. He needs to date inside his own league, not judging or anything but it’s clear to me his hips don’t exactly have full range of motion. He needs to be realistic about who would find him attractive. We are sexual creatures, no use pretending it’s not true.

  82. definitely Haley Joel Osment, his sister Emily was an actress on Hannah Montana.

    he does look very different, but seems really nice and relaxed. if he lost just a little weight and cut his hair, I think he’d be fine.

  86. Actor: Haley Joel Osment

    [Optional] Do you think he’s still cute? He’s not my type but there somebody for everyone.

  87. Haley Joel Osment and his sister Emily Osment
    No, I don’t think he’s still cute at all.

  90. I think this is Haley Joel Osment. The picture looks like him now and his sister was in Hannah Montana.

  95. Haley Joel Osment

    I think he could be cute…if he has shaved that awful beard and maybe lost a few pounds.