I got a very interesting question from an Internet friend, about a new girl that he is dating. He loves natural woman, but the woman that he just started dating does not have natural hair. So his question to me is, how does he let her know that she would be absolutely gorgeous with her own natural hair??
Here is my advice to him:
I think approaching the subject of asking a woman, that you are just getting to know, to be more natural is very touchy. If she brings up the subject, then your in!! But if its not something that she talks about, it may be hard to bring it up without offending her.
If you are just starting to date, I would say wait awhile, until you have established that you really love the way she looks and carries herself. Once you are both kind of over the initial newness of the relationship (give or take 2 or 3 months), I think it may be ok to ask her if she would ever consider wearing her hair naturally.
But!! And this is a big but! You have to be ready for her to possibly reject the idea. She may like her own style or way of presenting herself to the world. And if she says she is not into it, you may have to just respect that. In my own situation - I entered my relationship with my husband with permed hair. I already had a huge desire to go natural. So when he brought it up and encouraged me to loc / dread my hair, I was all for it. So it really just depends on her mindset.
Hope this helps!