5 years. " Dating a man who is 10 years older can have benefits as well as pitfalls. Although each person and each relationship is unique, there are some general guidelines that can help you have a more successful relationship . May 11,  · im dating a 38 year old and im turning 20 in a month we get along great are are attracted to each other. i think age is just a # but some people dont see it that wayStatus: Resolved. They discuss the pitfalls (and surprising advantages!) of dating someone older, and occasionally My current boyfriend is 10 years older than me. So yeah, now would be a great time for me to get my lazy ass off my chair, and take some time from video game and drawing and put them into looking for boyfriend. I love the sweet relationship you two have and I appreciate you sharing the fun and not so fun parts of the age difference. Should I date a woman 10 years older than me? These are all things that people with age differences experience, but it seems like you all are able to work together to handle them. He saw past everything superficial and seemingly appreciated my soul.