And that dating game's chess still checkin’ for a mate

from Shad – Call Waiting (Interlude) Lyrics on Rap Genius

Meaning

In the the game of chess, you try to get your opponent in check (King being targeted) to get a checkmate (King has no escape) and win the match

Shad uses this as a metaphor to say that he is searching for a lover but has not found his soulmate yet.

To help improve the meaning of these lyrics, visit “Call Waiting (Interlude)” by Shad Lyrics and leave a comment on the lyrics box