One of the things that you’ll want to learn about your date is her career plans. Once you find out what she wants to do for the rest of her life, plan a date based around that thing. (And don’t forget that full-time parent is a fully legitimate career choice!)
Find someone doing the career that either you or your date is pursuing, and arrange with them to either follow them around for a couple hours or assisting them.
Watch Videos About Your Date’s Career Choice
Look up some videos on the subject of your date’s career choice, including steps that can be taken now to work toward that occupation. Talk about what you learn.
Attend a Conference
There are conferences on just about everything. Look up a local conference on the subject of your date’s interest or occupational goals. Invite them to go with you to it.
Go to a Company Party
If your job has a party, invite your date to come along. (Just be sure to check with the people in charge to make sure it’s okay.)
Plan a Presentation
Together, plan a presentation, lesson, game plan, or sales plan, or whatever follows the right career path.
If your date is going into a building, creative, or construction field, build something together. It could be big or small, so long as you do it together.
Hold an “Official” Interview
Tell your date you have an assignment to interview someone pursuing a career (I hearby assign you to do so—there, now you won’t be lying when you do it), and you’d like to interview your date. Ask questions to get as much detail as possible.
Come Up With Career Mission Statements
Sit down together and come up with mission statements for your career(s). Doing so can not only help you focus your efforts in trying to fulfill your dreams, but doing it together can help you come to know some of the deeper aspects of each other’s personalities.
Watch a Movie Based on that Career
Go to a movie based around your date’s career path, and use it as a launch-pad for a great conversation over dinner about your date’s goals, hopes, and dreams.
Go Shopping For Career Stuff
Most careers involve items unique to that occupation. Once you know your date’s career ideas, go shopping at some places that carry items that might be useful in that career.