A:Answer Built-in audio functionality of electronics usually only support one audio output at a time, so you end up with a "sound out of the tv" OR "sound out of earbuds" situation.
Some TV support "dual audio" or you can get a dual audio transmitter, but this only gives you a "sound out of 2 sets of earbuds" situation. Maybe that's not a bad thing, since you'll be able to share in his experience.
Back in the days, you would just get an audio splitter (Y-Cable) and plug in a speaker and a pair of headphones. Unfortunately, I have not seen a wireless version of this.