I think you are very alike in your personality, but due to the different Ascendant and Midheaven degrees, outer planet transits to these will happen at different times for both of you. This would mean that some major life events, such as important relationships, marriage and events pertaining to your education and career will happen at different times.
In Ryan's chart the Asc/Des axis is aspected by Venus and Neptune; he may be more idealistic, perhaps also unrealistic, about relationship and love issues.