Dating is hard enough as it is. Now, pile on mental health issues stemming from his or her past and its a recipe for disaster. So instead of finding out later that the person you’re dating may have some mental health problems that you didn’t sign up for, here are a few questions you should ask and they should answer (and you should answer too).

1. Do you like your job?

Why: Is the person about to make any major life changes e.g., leave their $200K/year job to go back to school? What’s their attitude to their work? Do they see it as a job, a vocation, or are they primarily motivated by climbing the career ladder?

2. What sort of vacations do you like to take?

Why: Different vacation preferences or amounts of vacation time can be a major source of ongoing incompatibility. For example, if one person likes to take very long trips and the other person has a more standard two weeks vacation time.

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