Why does iMessage take longer to send messages for certain conversations?

iMessage can take around 15-20 minutes to send messages to certain conversations, but is extremely fast for others (I've noticed that it's generally faster for relatively newer conversations) off of my phone (iPhone 4S running iOS 8). iMessages for the same conversations send infinitely faster off of my macbook pro.
It shouldn't be a wifi/data/network issue because messages sent for different conversations off of the same network take different times to send.

I would delete the contact and then have the other person(s) send you a Mesage and then readd them as a contact.

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