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Hi Mike, You can only connect and use one pair of Bluetooth headphones at a time. However, It does have the feature Multi-Output Audio, which allows you to turn on both the TV speaker and Bluetooth headphones at the same time. When this function is active, you can set the volume of the Bluetooth headphone higher than the volume of the TV speaker. If you want to connect two pairs of headphones simultaneously, I recommend our 2022 models, which offer Dual Bluetooth Audio, such as the Q60B: https://www.bestbuy.com/site/samsung-75-class-q60b-qled-4k-smart-tizen-tv/6502241.p?skuId=6502241#anchor=productVariations ~Samsung Advisor
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