It is safer to be sure that the file system is clean before resizing.
One way is to right-click the partition in GParted and select "Check" from the context menu. Then click "Apply" in the icon bar above the partition list - and let GParted do its job. Once you've run the file system check, the resize operation should work well.
Sometimes there are severe errors that can't be fixed by e2fsck, or hardware problems.
There is no way to "force" GParted to do the operation despite the check error result, because it could be unsafe for use by non experienced users. You can do resizing manually from the command line, from the terminal window.
Look at the man page for parted.
However I would suggest to try the latest stable version of the Gparted livecd first. Ubuntu always contains an older version, and we don't know if the dependencies are up to date.
(Moved to the Live Media section)
*** It is highly recommended to backup any important files before doing resize/move operations. ***