Well at the moment thats the way it is. Lucy is all the way back in Kanto while Brock is in Sinnoh. And with Holly developing a major crush on him through the double battles she'll be more likely the first to encounter him again.
So while Lucy opened up the Battle Pike for Ash because of her crush, Holly went out to train to become a better partner. About equal in terms of what they did for him, so their intentions aren't questioned its just simply the factor of distance right now.
"The hardest thing about dreaming about someone you love is to wake up but if the only place I could see you was in my dreams I would sleep forever"
Sorry, but Lucy will be given the same treatment that Anabel also received.
Now, I feel sorry for her. Lucy, not Anabel. I must say how she is kept in by her 'followers' bieing a barrier for it to continue. Fortunately tough the chances of Brock getting lucky, is slim
You're born, you take s-. You get out in the world, you take more s-. You climb a little higher, you take less s-. Till one day you're up in the rarefied atmosphere and you've forgotten what s- even looks like.