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Find out early if there are reasons that “making it work” will be fraught. Select a few of these questions rather than attempt to ask them all on the same first date! For example, if one person likes to take very long trips and the other person has a more standard two weeks vacation time. If asking this question leads to five solid minutes of them complaining you'll know the person sees the glass as half empty. Why: When you enter a relationship with someone you’re also entering a relationship with their friends. Why: If one of you doesn't like pets and the other has 3 dogs, that's likely to be a problem.