Another topic that will inevitably come up on the first date will be your family and the nature of your relationship with them (Family Guy shirt image courtesy of the cartoon t shirt category).
A negative relationship with your family can really put the average girl off. Don’t fall into the trap of having her tell you how horrible her relationship is and then assume that means she will be cool with your bad relationship. Double standards exist everywhere. She will not want to hear about how bad your family life is no matter how bad hers is.
On the other hand, if you gush too much about your family, especially your mother, you will look like a mama’s boy. A girl in the process of evaluating your ability to be a partner does not want to have to compete with your mother. Basically you need to strike a balance between loving and messed up.
Each person’s life is different, and in this you should not be making stuff up as if you develop a relationship this will bite you on the ass. Instead, tell the truth but use an old sales technique I used to use when I would be selling products I wasn’t gung ho for I like to call “Finding the Positive.”
For example, it would be fair to say my relationship with my father was not Ward Clever and the Beav. However, when I talk about him I try to stay focused on the few fun things we did, and try to see some of the messed up stuff he did in a humorous light. In retrospect most of the things he did that bordered on abuse can be seen as just quirky and funny (by the way, in my free time I am writing stories about my childhood with him).
By the same token, I am very close to my mother. However, I don’t mention that I talk to her pretty much every other day. I talk about being close but I don’t harp on it.
As for your brothers and sisters, feel free to say anything you want, as a messed up relationship with a sibling is not an abnormal thing. Just make sure you end the story with something like “We used to fight all the time, and I don’t talk to him/her much anymore, but of course I still love him/her).
By the way, brothers, sisters, and cousins can be a great source of amusing anecdotes that don’t actually reveal a lot about you. I have yet to even tap that keg, but believe me there is no shortage of material.