Hey beehappybrii,
Since iMessages are sent and received via cellular data or Wi-Fi, check to make sure it isn't network related. Does this happen when connected to a cellular network, a Wi-Fi network, or both. If one works as expected and the other doesn't, you'd want contact your wireless carrier or your Internet Service Provider.
If the issue occurs with both your cellular data and a Wi-Fi network, follow the steps here: If you can't send or receive messages on your iPhone or iPad. Specifically in the section labeled "If you still need help".
Take care.