#1 isn't really clear. Does this mean that one time each month, he tattoos a rose on a person, and then next month, another rose tattoo on another person? Or is he tattooing a rose on himself every month?
#2 is grammatically correct, but the word "woos" is not used much at all anymore. It mostly shows up in pre-20th century stories.
1. He tattoos a rose once a month.
2. He woos the girl every weekend.
(Are both grammatical? Do you use 'woos' frequently in daily conversation?)
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