The You look pretty thing is more like when she gets a haircut..."your hair looks nice" or when she changes a profile pic..."that's one of the best pics of you, you look pretty in that"
H sent me an email saying that I looked hot in my profile pic...made me cringe. Gave me a slight ego boost but really felt kind of pervy under the circumstances. I would stick to in person compliments if any and be sincere and specific. But you don't really need this right now. IMO.