I witnessed the Prophet ﷺ in the mosque more than a hundred times while his companions discussed poetry and matters from the days of Jahiliyyah, and at times he would smile along with them.
حدثنا أسود بن عامر حدثنا شريك عن سماك
شهدت النبي ﷺ أكثر من مائة مرة في المسجد وأصحابه يتذاكرون الشعر وأشياء من أمر الجاهلية فربما تبسم معهم
Its chain of transmission is hasan, mentioned previously in 20736.