Wait 7 days. If after that you still cannot contact the winner, go to your created giveaways page, and hit the "request a new winner" link on that giveaway, and select the "can't contact winner" option. A new winner will be selected from the giveaway entrants.
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The rules don't require anyone to accept your friend request. The default method for contacting winners and passing on gifts is email. If you try to contact them on Steam and they decline your request or they simply are never around the same time you are around, and they don't get the game, then they have every right to mark it as not received.
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It's more about winner saying he didn't received anything and key (one that he sold) doesn't work now, then he'd say "you just wrote it now to blame me".
You probably wouldn't have those troubles (100+ giveaways makes you a bit trustworthy :) ), but someone like OP could get in stupid troubles. That's why it's the best not to send keys in mails, or at least not in first one (one where you'd write "hey you won my giveaway, I've added you on steam to talk").
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I feel your pain. It's frustrating to see those contributor giveaways and not be able to enter because you're being held up by somebody else through not fault of your own.
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I have been waiting 2 days for his reply but he doesn't seem to answer me or even read my mail.. What do i do now?
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