The dinner outing was 33-year-old singer and the tycoon's first date together, reported TMZ.
In the pictures obtained by the website, "Oops!...I did it again" hitmaker could be seen sitting at the dinner table wearing a white top paired with black skirt.
None of the two have confirmed or denied the dating reports.
Spears split from her boyfriend Charlie Ebersol in June, after eight months of dating.