You'll lose nothing for giving it a try.
Boss, define your mission first. Is it long-term, short-term or a hit-and-run?
If your mission is to land on Venus, prepare a one month strategy(too long).
This is how the strategy proceeds. Two coffee dates, a lunch date, and a drink date. Be simple on each date, and have some nice cologne.
If you do not succeed on the first drink date with her, give it a second chance. More than one month with a Nairobi chic without landing is an abomination.
Live Full Die Empty - Les Brown.