How to ask questions when date a crossdresser or a trans woman?

Do you trust other people easily?
From his answer to this question you can know a lot about your partner, such as whether he can really trust other people, whether he feels secure when get on with stranger, and is he trustworthy?
How do your friends describe you?
The best way to know someone is to ask his friends or families, but it is impossible to ask his friends in the first ts dating, you can ask this question to your partner directly.
Do you have a plan for future life?
Most of people like to talking about future plan when dating a trans woman or a corssdresser, because it shows that they are serious to the relationship.