Imagine doing a full-on practice date with a coworker before going on a real date with your crush, complete with a fancy ass dinner.
At that point just go out with the coworker, they’ve proven to be more invested in your happiness than a what-if crush.
What’s next, is he going to ask his coworker to practice his skills in bed? He might not be ready for Tokimori despite sleeping in the same bed as her.