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I am curious if it is proper grammar when referring to two individuals having possession of something to put apostrophies on each or just the second....or is there a more grammatically correct to express the same.

See example below.

Given the benefits of discipline with dignity as well as alternatives to zero-tolerance policies, I find Curwin's and Mendler’s approach desirable.

or

Given the benefits of discipline with dignity as well as alternatives to zero-tolerance policies, I find Curwin and Mendler’s approach desirable.
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Hi and welcome to the forums!

Here's what I learnt...

#1 "... Curwin's and Mendler’s approach ..." => OK if Curwin and Mendler had two different approaches.

#2 "... Curwin and Mendler’s approach ..." => OK if you're referring to one single approach, shared by Curwin and Mendler.

Hope I learnt it correctly. Emotion: stick out tongue
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Tanit#1 "... Curwin's and Mendler’s approach ..." => OK if Curwin and Mendler had two different approaches.
For this meaning I prefer to write:
Curwin's and Mendler's approaches.
CJ
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Thanks for your welcome and reply! Emotion: smile

I was attempting to convey the meaning of your #2. The way you express the utility behind using one form or the other makes a lot of sense.

Thanks again.
 CalifJim's reply was promoted to an answer.
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Well, now it makes more sense! Thanks, CJ.
Emotion: wink