If you'd like to dual-boot Windows and Debian, install Windows first (sugg. 20GB partition), and leave the rest of the drive as free space. Then install Debian (sugg. 20GB partition) where you'd like and Grub should automatically run grub-update to include the Windows loader.
Because sharing files between Windows (NTFS) and Debian (ext3, ext4) can be such a hassle, I recommend the following setup, which allows a large Fat32 partition to hold all non-OS files and be mounted in either OS.
20GB: Windows
20GB: Debian
Rest: Fat32
You'll have to specify the free space as Fat32 when installing Debian, and later run mkfs.vfat -F 32 -I /dev/sdaX (X is variable) to format the partition as Fat32.
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