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If you find yourself in an intergenerational relationship, making sure you have common goals is more important than ever. Generational differences, as well as being in different stages of life, complicate May - December dating and marriages. Ideas about marriage, having children, finances, retirement, etc. need to be compatible. The larger the age difference, the more difficult it may be to find common ground when it comes to key life goals. If the age difference is considerable, one person may be thinking about retiring when the other wants to start a family. By discussing your ideas of the future and each other's life goals, the two of you will have a better chance of working out your relationship. Dating someone who is remarkably younger or older than you is a definite challenge. It is important to make sure you both share the same goals and dreams.