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Pretty simple, like the title says, what's the difference between いつだって and いつでも? I can tell there's a little difference, but it's so very difficult for me to pin down.

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「いつだって」 is a more casual way of saying 「いつでも」 and it has a little emphasis on its meaning compared to 「いつでも」. You'll hardly see 「だって」 being used in newspaper articles compared to 「でも」.

だって　source: デジタル大辞泉 (http://dictionary.goo.ne.jp/leaf/jn2/137401/m0u/)

［係助］《断定の助動詞「だ」に係助詞「とて」の付いた「だとて」の音変化という》名詞・副詞、一部の助詞に付く。「でも」に似るが、語調がより強い。

Also this might be of your interest: http://dictionary.goo.ne.jp/leaf/thsrs/17174/m0u/

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  • Would you say: "いつだってうちに来てください"？
    – Axioplase
    Oct 1, 2012 at 7:16
  • You can say it. It may sound　slightly awkward though depending on the situation. I would add ね at the end like 「いつだってうちに来てくださいね」 or 「いつだってうちに来てね」. Without ね, 「下さい」 is polite but feels a bit formal by itself. ね creates a friendly effect so it corresponds to だって.
    – Teno
    Oct 1, 2012 at 23:25

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