setting up wireless headphones via the DTV streaming device.

You would have to use Bluetooth Headphones. 

I've got those, I am trying to hook up the base unit for the headphones to broadcast the signal to the headphones. Looking to get the output of signal to that base unit. Seems pretty simple but alas no sound.

What Bluetooth headphone brand/model do you have?

The DirecTV Stream box can be paired with most Bluetooth headphones directly. No need for an intermediate Bluetooth add-on. 

Well, that could be the issue the are radio frequency not blue tooth. So I can go direct hook up to the box? 

What is the brand?

Rosadi, an off brand for sure.

ludwick577,  I have ordered JBL wireless headphones, do we have some instructions on how to set them up on the media box?

I have Blackweb and JLab earbuds and haven’t had luck pairing either with the Gemini box. I get as far as”Bluetooth pairing request from (name of earbud)” It prompts pair or cancel and when I click ok for either option nothing happens. The screen remains the same.

Is there a pairing or on button on your earbuds? I have a small bluetooth soundbar and it finally paired when I hit the on/pair button.

Yes there is on both sets I have. One is JLab another Blackweb. The speakers say Bluetooth ready to pair. I sometimes get as far as “Bluetooth pairing request from Blackweb” with option to choose PAIR or CANCEL. This is where the problem is I believe. When I enter ok for either option nothing at all happens on the screen, but I do see the blue light blink on Gemini so I know it’s communicating. Maybe it’s not made for earbuds. I have hearing problems and thought this would be a great fix so my family doesn’t hear the tv so loud😃 I’ll have to hook my ROKU back up instead. Thanks for trying to help.

I have just connected a pair of Sennheiser wireless headphones (NOT bluetooth) Disregard the other responders who have mentioned BLUETOOTH because that is not what you are asking... you are asking about connecting wireless headphones to the Directv streaming device via the optical/digital audio out port. My Sennhesier RS-195 transmitter had a digital port and an analog port. I used the supplied digital optical cable supplied from Sennhesier to connect the transmitter to the Directv Streaming Device's digital audio out port. I then had to update 2 settings on my tv. 1st was changing audio setting to PCM and the 2nd was to change sound setting from surround  to stereo. Until I did this NO sound came out of the headphones. If you have Bluetooth headphones then you DONT connect via the audio out port on the streaming device but INSTEAD connect via the bluetooth setting on your tv if your tv has bluetooth.  You simply pair the bluetooth headphones to your bluetooth tv. My headphones AREN'T bluetooth so I connected them as first described which is the question you asked. 

I have been trying to pair my wireless headphones to the streaming boxes too.  I cant get them to pair.  they will pair with the tv but then I am the only one who can hear.  I had this set up previously with dish I figured i should be able to do the same.  I have a hearing loss and the headphones help me hear without blowing everyone else out of the. room.   any suggestions ?   I did have to purchase a little USB connector, which I am willing to do if it will work.  Any help is appreciated.

I have the DirecTV streaming USB dongle device, and want to pair a set of Beats headphones with it, but the DTV device never finds the Beats OR my AirPods Pro for that matter. Thanks for any advice.

NM. Problem solved. I just paired my Beats and AirPod Pros to the TV instead of the DTV dongle. Why even build BT into this device if it won’t pair? 🤷🏽‍♂️