Should you confess the number of times you commit a venial sin?
You should give at least an approximate number of times (if you don’t know or can’t remember, just say numerous) if the priest needs more information he will ask.
Only mortal sins need to be confessed in number and kind.
Can. 988 §1. “A member of the Christian faithful is obliged to confess in kind and number all grave sins committed after baptism and not yet remitted directly through the keys of the Church nor acknowledged in individual confession, of which the person has knowledge after diligent examination of conscience”. *
There is no “should” there.
One “may” give a number* but it is not needed for venial sins.*
For venial sins it’s not needed. I do tell the priest if a venial sin is a real problem for me in order to help him with his counseling, but it’s certainly not necessary.