My iphone sends old messages, message not delivered

So the other day I began having troubles with my phone. It's only been with one person in my contacts at the moment, but it's happening frequently enough to be irritating and concerning. Especially with the amount of texts I'd normally be sending.
When I message this person, more often than not, a little red circle with an exclamation point pops up next to the sent message, and beneath it reads "not delivered".
According to the person I text, they still get a message, however the messages are always older messages. Sometimes duplicate, but not always, it seems. The most recent duplicate was originally sent around 8am, and resent instead of a message sent around 3:30. The original message did not have the undelivered problem.
I have the iphone 4, this person has a phone that is not an iphone.
Today I went into a Verizon store and asked for advice. He told me to turn off iMessage, and that that should fix it, however I then sent another text and it once again marked it as not delivered, and sent an old message instead.
Please, does anyone know how to fix this?
Thanks.

That means whoever you're trying to send an iMessage to either has iMessage turned off or doesn't have a data connection. There's nothing you can do on your end. The message will be held on Apple's servers for 24hrs, then deleted.

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