The ability of connecting headphones to a walkie talkies will depend on the model of the walkie talkie. While most walkies allow for headset connection, the audio jack on the walkie might differ from each brand/model so do a quick check on what kind of audio jacks your intended walkie talkie uses before commiting to it. Some common audio jacks include a single 2.5mm jack plug and a two jack plugs (one 3.5mm and the other 2.5mm). However, to make things more complicated, just because the physical appearance of the jacks look similar, the internal wiring may not be. This might lead to cases where the headphone is able to be plugged in but no connection is generated due to different internal wiring. Thus, to ease the confusion, some brand/model includes a headset with the purchase.