My date knows more about my family than I do.

LegacyUser

Hey I grew up in fostercare, staying with the same family since I was a kid. But I've recently started to reconnect with my birthfamily.
The other day I added the members of my birthfamily to my facebook account. I also added one of the people who was in the suggested friends list cause he looked cute and is gay. (Whatever, right?) Let's call him Ben. I'm 20, he's 19.
So me and Ben get talking over Facebook. It turns out that he is the brother of my female cousin's boyfriend and he's known my family since he was born. He knows a lot more about my family than I do and he's seen them a lot more than I have, as his family's really close to them. We're going on a date soon but isn't it weird how he knows my family a lot more than I do? If we end up dating, will this lead to any problems? A large part of dating is getting to know about the other person's family but he knows them more than me!
Also, I happen to be transgender. I asked him how he feels about trans people (by mentioning Miss Caitlyn Jenner) and then I told him that I'm trans. It turns out that he's also trans and that he came out to one of his friends a few days ago. He's now around the same place as I am in terms of the transition (just started coming out but not yet ready to tell the family). I am a little bit further in the sense that I wear girls' clothes in public and I've promised that if he ever needs help or he wants to go clothes shopping, I'll help him if he wants.
So we have a surprising amount in common but a part of me feels like this is too good to be true (we have way too many coincidences-the gender stuff and how close he is to my family) and another part of me doesn't want to blow it. We've both said that, if the date goes well, we're always open to the idea of more dates. But I haven't had a proper date in ages. How do I act on the date? What kind of stuff do I say? Any advice :P
We're getting some food and then going to the cinema. Should I pay for the tickets or do LGBT couples both pay?

note: he wants to keep male pronouns for the time being, hence why I haven't referred to him as she.

J_E

Oh boy, this is a loaded one. There are so many different angles here that it's hard to know where to start. I personally don't know about the whole Facebook thing but have you actually voiced to him about the relationship between your families? Just be yourself on the date but don't immediately lead into discussion about the family business - honestly it varies who pays there is no rule, sometimes people do it by turns, sometimes split. Just see what happens and don't feel awkward about it. Honestly, the whole family thing there is too little info and frames of reference for me to even talk about that.

Fleawuss

Wait and see.

irish_dave_83

Going on a date is nerve wrecking enough, without bringing up your family. As you said you already appear have a lot in common, so that should fill the conversation. You will get a feel as to whether you click or not as the conversation flows. I would wait to have a deeper family discussion until you are a "formal couple". At the moment just have fun and treat him as if it was someone who didn't know your family if possible.