To split your actual audio into two paths (one to stream, another one to your headphones only) you need two sound-devices.
If your machine distinguishes between speaker-output and headphone-output on the soundcard, you could go for this.
If not, you need software with virtual audio devices like Banana Voicemeeter. If interested in the latter, follow up the hints given here: https://obsproject.com/forum/threads/split-audio-monitoring.144493/post-528988
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