English Translation
How did your date with Tom go?
“Jalannya” (the way) sounds unnatural. It should be dropped from the sentence.
A native Indonesian speaker on Tatoeba also supports my opinion. See the detail here.
The Indonesian sentence was updated by the Clozemaster admin on September 25, 2022.
Old: Bagaimana jalannya kencanmu dengan Tom?
New: Bagaimana kencanmu dengan Tom?
20K Most Common Collection incorporated the updated one, but Random Collection and Fluency Fact Track haven’t done yet.