I enjoy wearing women’s underwear. I don’t want to full-on cross-dress, but I really like the feel of having frilly panties on under my clothes.

How can I break this to a date so she doesn’t freak out when we start getting naked? — T.N., West Virginia

I wasn’t sure how to best answer this question so I asked Ilaria, a former cross-dressing man, turned woman, turned lingerie designer and lingerie fetishist for her advice. This is her flawless answer:

“I would suggest first asking her some subtle questions about gender role and gender identity to find out how accepting and open-minded to she is. You could start off with a lighthearted question about how she feels about stereotypical gender roles, blue for boys and pink for girls and gay and lesbian rights, etc.