Using two headsets on my MacBook Air I want to rent a movie on my MacBook Air and my husband and I want to watch the movie together using two separate headsets. Can this been done. I have 3 headsets to choose from, Wireless Bose, Logitech  usb plugin and a set that uses the pin plug in. I am not able to bluetooth my bose - only works on my iPad. The other two pin plug in and USB plug in only allows one to work at a time. Is it possible for both of us to watch a movie using separate headphones on MacBook Air??
You need a Y cable splitter to connect 2 headsets.

Most come with single audio control but there are some with dual audio volume. If you already have audio volume control on each headset then no problem.

Since you have the headsets already with different plugs you will have to get appropriate cable splitter for that.

I did some search for you.

First the USB male to 2x Female splitter like this.

One you use for your USB Head set.

For the second headset you need another adapter like this.

Those do not have Volume adjustment, so hope there is no problem with that :).