Having trouble synching IPhone calendar with two computers

I used to be able to synch calendars, via my Iphone, between my windows-Outlook calendar on my gateway and the ICal on my IMac. Now, for some reason, when I synch with the IMac, via ITunes, everythng on the Iphone is replaced by the info on my Ical even though I request a "merge". Any thoughts as to why?

i have 2 macs, one for work and one for home, and everytime i synch my calendar with my work one, it deletes my movies (which aren't itunes bought, as well as music. How do i synch to two computers without losing the content i clearly own but which is only on my home computer? Any advice greatly appreciated.

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