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Meet Tyler Oakley, Winner Of The GayCities 2012 Pride Photo Challenge

Who says dreams don’t come true? Just last week, GayCities member Tyler Oakley was a cute kid with a bunch of YouTube followers, who enjoyed the quirky queer videos he posted from his Castro apartment.

Today he is the official winner of the GayCities 2012 Pride Photo Challenge!

Tyler’s photo, “Castro Pride,” took the grand prize, thanks to what can only be described as brilliant strategy: promising to personally meet and greet fans who voted for his photo when he takes his prize—a trip to New York City sponsored by our friends at JetBlue and Kimpton Hotels.

Of course, it didn’t hurt that his photo was simply adorable.

“I’m really excited to be heading to New York now that I’ve won the GayCities Challenge,” Tyler gushed when he learned of his victory. “Connecting with [people who watch my videos] is my absolute favorite thing in the world.”

Congrats to Tyler and the second place winner, GayCities member Daniel1776, who receives two nights at any Kimpton Hotel for his photo, “KeyWest, Florida, Pride” (at left).

Check outa slideshow of the finalists and photos from all the GayCities members who entered the Pride Photo Challenge here!



    • Tyler Oakley

      Thanks for everyone who voted! I’m really excited to meet so many people while I’m in NYC, and hopefully a majority of them will be fans from the city who took the time to vote for me. Thanks GayCities, Queerty, JetBlue, and Kimpton!

      Jul 18, 2012 at 4:09 pm · @ReplyReply to this comment ·
    • Sam Luigi

      Yay Tyler!

      Jul 18, 2012 at 4:10 pm · @ReplyReply to this comment ·
    • Kate Bushwhacked


      Jul 18, 2012 at 4:11 pm · @ReplyReply to this comment ·
    • San Fran

      This photo was from Castro Street Fair. Not pride.
      Still a good pic, just saying.

      Jul 18, 2012 at 4:33 pm · @ReplyReply to this comment ·
    • JRB

      Oh for Christs sake, seriously?

      Jul 18, 2012 at 4:47 pm · @ReplyReply to this comment ·
    • Amanda

      Way to go Tyler. :)

      Jul 18, 2012 at 5:55 pm · @ReplyReply to this comment ·
    • Carlos G.

      Tyler OAKLEY is FIERCE! Congrats gurrrrllll!

      Jul 18, 2012 at 5:56 pm · @ReplyReply to this comment ·
    • Ash

      Yay Tyler!! Congrats!!!

      Jul 18, 2012 at 5:57 pm · @ReplyReply to this comment ·
    • Tony

      Gurl, werk! Congratulations Tyler, you deserve it!

      Jul 18, 2012 at 5:58 pm · @ReplyReply to this comment ·
    • edity

      aww Tyler your smile is so precious.

      Jul 18, 2012 at 5:58 pm · @ReplyReply to this comment ·
    • Roni

      YAY TYLER!!!! Congrats!!! You deserve it :)

      Jul 18, 2012 at 6:00 pm · @ReplyReply to this comment ·
    • Sophie

      Yay Ty!! Congrats!!! Looking forward to meet you!

      Jul 18, 2012 at 6:00 pm · @ReplyReply to this comment ·
    • RT

      no one says “dreams don’t true” but congrats anyway!

      Jul 18, 2012 at 6:00 pm · @ReplyReply to this comment ·
    • Fodolodo

      Yay! He is so wonderful.

      Jul 18, 2012 at 6:01 pm · @ReplyReply to this comment ·
    • Allie

      YAY TYLER! congrats! you deserve it :) have fun meeting everyone

      Jul 18, 2012 at 6:03 pm · @ReplyReply to this comment ·
    • Florencia

      Yay for Tyler! :D

      Jul 18, 2012 at 6:09 pm · @ReplyReply to this comment ·
    • Kallie

      Go Tyler! Get it, guuurrrrlll. <3 :D CONGRATS!

      Jul 18, 2012 at 6:10 pm · @ReplyReply to this comment ·
    • Michelle

      Tyler is great and he totally deserves his time to shine!

      Jul 18, 2012 at 6:11 pm · @ReplyReply to this comment ·
    • laci

      CONGRATS tyler!!!! :)

      Jul 18, 2012 at 6:16 pm · @ReplyReply to this comment ·
    • Brendan

      Woot! This is so awesome. Congrats!

      Jul 18, 2012 at 6:25 pm · @ReplyReply to this comment ·
    • Olivia

      Congratulations tyler!! won’t be able to meet you becouse i live on the other side of the world (sweden) :( but i’m very happy for you! ;D

      Jul 18, 2012 at 6:39 pm · @ReplyReply to this comment ·
    • cruz

      did someone vet the veracity of this photo actually occurring on a gay pride weekend in SF this year? this looks more like castro street fair with it’s food vendors lining up corner of market and castro during this event, which happens every year in october. and where are the gay pride flags that usually line up market street in june? i didn’t know that you could just submit any picture from any event, so long as it contains a gayface.

      Jul 18, 2012 at 6:51 pm · @ReplyReply to this comment ·
    • no one

      Thank you for making stereotypes a reality by winning with this picture.

      Better still, winning a “pride photo challenge” with a picture not from pride.

      You turned an artistic contest into a social media one.

      Congrats.. I think?

      Jul 18, 2012 at 7:37 pm · @ReplyReply to this comment ·
    • no one

      Additionally, Tyler since you are in the picture shouldn’t the person who took that photo of you have won?

      You did nothing but mediawhore yourself out to win.

      Jul 18, 2012 at 7:40 pm · @ReplyReply to this comment ·
    • Nancy

      Congrats, Tyler!

      Jul 18, 2012 at 7:56 pm · @ReplyReply to this comment ·
    • DamienEvans80

      The Tyler Oakley haters need to just move to the left. Tyler does SO much not just for his fans, but for the entire LGBT community. We need more people like Tyler in the world today. I adore him and not just because he’s absolutely precious and adorable. If I could meet anyone in the world, it would be Tyler. He is such an impressive inspiration to me and to many. Thank you Tyler, I and many others love you!

      Jul 18, 2012 at 8:04 pm · @ReplyReply to this comment ·
    • ballerinanerdfighter

      People don’t realize how caring Tyler Oakley is. When I met him in person he had been taking the time to get to know everyone and have a conversation with them each. He also supports the LGBT community so much as seen in his very large support of The Trevor Project and other LGBT causes. He is an inspiring person, so please, do the research before you judge others.

      Jul 18, 2012 at 9:48 pm · @ReplyReply to this comment ·
    • No Tea No Shave

      Tyler looks sexy every season of the year and every day is Pride Day in SF. Love that angle and it capture the liveliness of the Castro perfectly. Congrats on a good win. NYC get ready.

      Jul 18, 2012 at 10:06 pm · @ReplyReply to this comment ·
    • jj

      Anyone else notice how the times of all the Congratsss tyler!!! comments are all within 5 minutes of each other. busted! get a life tyler

      Jul 18, 2012 at 10:47 pm · @ReplyReply to this comment ·
    • allie

      congrats tyler!!!! youre too cute, ive lost my ability to even! when are you going to be in NYC???

      Jul 18, 2012 at 11:32 pm · @ReplyReply to this comment ·
    • Gavin

      Tyler – you are AMAZING. So glad you won this. You define us new gays and represent so well. Enjoy NYC :)

      Jul 19, 2012 at 1:09 am · @ReplyReply to this comment ·
    • Miki

      I’m so happy for you Tyler! I hope everyone has a great time in your meet up!

      Jul 19, 2012 at 3:15 am · @ReplyReply to this comment ·
    • Donny

      This misogynistic piece of crap? Okay.

      Jul 19, 2012 at 6:15 am · @ReplyReply to this comment ·
    • Truthful

      I puked a little.

      Jul 19, 2012 at 11:51 am · @ReplyReply to this comment ·
    • San Fran

      How is it being a hater by pointing out factual statements about this picture not being during pride. There were many applicants who took pride photos for the ‘pride photo contest’. Some people are just pointing out that this photo was from Castro Street Fair which isn’t even in the month of gay pride…so it’s kind of a stretch to let this photo classify as a winner of a pride photo.

      Not hating, just observing. Someone can be as sweet and cute as they want, but if they win by not following rules, it seems disrespectful to those who did follow the rules.

      Jul 19, 2012 at 1:16 pm · @ReplyReply to this comment ·
    • Alex

      I don’t know that the picture has to be from a pride event. It just says that it has to show pride in your city. It just looks like a crowd of people though…even if it is Castro.

      Jul 21, 2012 at 1:50 am · @ReplyReply to this comment ·
    • David

      Tyler Oakley is one of the biggest attention whores out there. Besides saying that he’s against bullying then doing nothing but attacking people on his blog to cyber-stalking people that criticize him Oakley has done nothing beneficial for any of us or the community.

      It’s especially sad to see him steal an admittedly awesome prize from someone who actually did put effort into their contest entry just because a vain, self indulgent photo (that he didn’t take or feature anything pride related) got far more votes from all of the people that follow him and fell for his pleas to like that picture.

      Aug 3, 2012 at 7:27 pm · @ReplyReply to this comment ·

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