I don't necessarily think drake texting milly bobby brown about boys is creepy
Why do you think that Drake's texting is not creepy?
It all depends on age and what they compare. My friends text me about everything and some of it could be weird if taken out of context.
You may not think that Drake texting about boys is ok, but comparing you and your friends text habits to his is judgmental and inconsiderate. Keep your thoughts on your own behaviours and stay out of other people's lives.
I am not a threat to my friends, I won't complain about their texts behavior.  We keep in between ourselves.
As long as you are not texting about anything illegal and all of you are comfortable, I do not see anything wrong with what you are doing.