I agree with the others. Just do what feels natural and organic. Let me tell you my experience: this literally just happened an hour ago. I am new to H, and I actually went in yesterday for the first time and met a great SA. Unfortunately, I did not have that much time in the store because I had somewhere to be so I felt like even though I had a great experience (and purchased some awesome twillies I was after), I knew I could have spent more time to get to know the SA and visa versa. I had a strong feeling that I should go back again today. I dont know why I felt that way but it just came to me. I called over there and remarkably they actually answered the phone and my SA actually was nearby when I called so they gave the phone to her and we spoke. She was very glad to hear that I wanted to come back to check out more things and we scheduled an appointment for later that day.
My second time in the store was even better than the first. I really got a chance to connect with the SA. We laughed and joked about things, and it seems we have some things in common. She took her time with me and really showed me even more this time around.
We spent more time talking about all sorts of things and as we were headed down from the shoe dept, and she said "you know you can always text or email me things you want etc." Evidently she had put her card in my receipt yesterday, but I didn't even realize it. She kept emphasizing to please text her about anything I may see.
As she was ringing me up for my purchases, she said it would be great if you emailed me a list of items you like. At that point in our conversation I felt like it was appropriate for me to ask "what about items that I am working towards," and she said "like a Birkin or Kelly, absolutely, send me everything, especially that." I was so excited that she was receptive to me sending her a list already but the whole conversation came about naturally. She mentioned sizes that she thinks are great and I told her that I will send her but I know that most people want exactly what I want, and she said not to worry and to let them worry about it. She then asked me to send her my full list several more times before I left. It was a great meeting, and I feel like I have found a great person at H for me.
I would highly recommend just bringing it up. It was a little intimidating at first but the conversation that came after was great and nothing to be scared about.