Hi Sarah. Yes, sleeping with the dilator in gets MUCH easier. Try taking some Tylenol PM or Advil before bed. Also, make sure you put extra lube on the dilator. I remember being really uncomfortable at first, but I promise it gets better! Some mornings I even forget I have one in!
How long are you leaving pink in before trying blue? At first the only way I could get blue in was if I dilated with pink at least for an hour. Also, sometimes even now when inserting blue(&sometimes pink) I notice it kind of “gets stuck” after the tip. I just have to push it a little harder to get the rest in. But it’s not painful at all. During the beginning of intercourse with my husband it normally does the same thing!
You are doing great! Hope this helps! 🙂