An important objective of dating is to make sure that the whole you is accepted by the other person.  It is not worthwhile to withhold or hide this information.

You want to be certain that they know who you are and are OK with all of you. Especially the areas that some people may be upset to find out later. You must share anything that will impact their life should they join their life with yours. The drama in your family, your student debt, your unusual habits, medical conditions, mistakes that have still impact your life, whatever.

Firstly, it would be a betrayal of trust if you do not share something that will really impact the other person’s life.

Equally important, you want to know that the other person knows about – and is OK with it.

Your goal is not only to share it, but more importantly, to make sure that you know that they understand it fully and accept it. You might ask them to tell you what they understood from what you shared. Be sure to clarify anything.

There are some things that are important to some people and not others; if this is area is important to them, you really ought to share. (For example, many people are OK with the ‘unusual relatives’, for some it is important to join what they term a ‘normal family’.)

You do not have to share things from your past that really will not come up again, such as mistakes you made and learned from. On the other hand, if you truly learned from them and that is part of the person you are now, it might be worthwhile to share your journey as a badge of honor and growth.