Not sure about insurance differences between Canada and the States, but
if the person has full coverage on the vehicle it should include
coverage for any person that drives the particular vehicle. Otherwise
if you have personal auto insurance and are covered to the max, it
should insure you to drive any vehicle. Check with your insurance
agency first if you are worried about it, but one way or another if you
both have full coverage it should be fine.

And if you are really worried about it, DON'T CRASH!! :D

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You must be a real bad driver if you are that worried about crashing.
You should just stick with your bicycle.

Besides, crashing is probably the least of your worries.  Whenever you
buy a car, you should always test it for flammability.  You dont want
to burn to death in your car, and some cars burn far too easily.  When
you buy a car, take it for a test drive, and then see if it burns.
The best way to do this is to pour a gallon of gasoline on the seat
and toss a match in the door, then slam the door and run.  If the car
burns, you dont want it because its too flammable.  If it dont burn,
buy it.  However, if it does burn, you either want to be covered by
insurance, or simply have a friend set an electric pole on fire and
tell the guy the pole ignited the car.  Electric poles often start on
fire from electrical shorts and the power company will pay the
damages.