I would suggest updating manually by downloading and installing the latest version from the Android Studio homepage. Depending on the "jump" in versions (eg from 1.9 to 2.1), this will either update the currently installed version or install the new version alongside it, letting you import your settings from the old version. The updated version should then be able to check for updates correctly.
Otherwise: Try deleting the Android Studio settings folder in your Windows user directory. Are you behind a proxy? Make sure your PC's date/time settings are correct.
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