Ask your date whether they consider themselves more introverted or extroverted. Introverts are those who prefer to be alone or in smaller groups, while extroverts are more outgoing and social. Different personality types won't necessarily form an incompatible couple but it is important to know your partner's category to communicate well.
Extroverted people will be more likely to engage in small talk and will also speak more freely than an introvert. Introverted people generally won't appreciate idle conversation and will probably be less open about their feelings. Neither type is better or worse than the other but the two tend to communicate quite differently.
Ask whether your date is more of an optimist or pessimist. This determines whether the relationship will have a healthy balance between optimism and pessimism. Although extreme optimism can lead to risky behavior and poor decision making, having a positive outlook is healthier than maintaining a pessimistic view of life. If one partner is more optimistic than the other, he should try to help the other think more positively. Likewise, a realistic partner will be able to point out potential risks to a partner who is overly optimistic.
Some people feel that there is no harm in telling a "white lie," while others want nothing but the truth at all times. This is an extremely important factor to discuss as trust is crucial to any healthy relationship. Ask your partner questions such as, "How important is honesty to you?" or, "How do you feel about white lies?"
Ask your dating partner how they get along with their family. Whether your partner comes from a healthy and happy home or from a dysfunctional family, their background will affect the way that they communicate, as children learn communication skills by observing how parents and other relatives interact with each other. It's not impossible for someone who doesn't have a good relationship with their family to communicate well with a romantic partner. If you know about a partner's family history you'll be ready to be patient and understanding about any communication issues that arise.
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