Hi haley.moz,
Thanks for visiting Apple Support Communities.
It sounds like you can't send or receive images via iMessage to some contacts, and you only see an empty speech bubble. You've tried some good steps including restarting your iPhone and turning iMessages off and back on.
Next, try these tips from If you can't send or receive messages on your iPhone, iPad, or iPod touch:
- Make sure that you’re connected to a cellular data or Wi-Fi network.
- Go to Settings > Messages and make sure that iMessage, Send as SMS, or MMS Messaging is turned on (whichever method you're trying to use). Learn about the different types of messages you can send.

- Restart your device.
- Check for a carrier settings update.
- Check for an iOS software update.
- Go to Settings > Messages > Send & Receive, tap your Apple ID, then tap Sign Out.
- Go to Settings > FaceTime, tap your Apple ID, then tap Sign Out.
- On your iPhone first, sign back in to iMessage and Facetime.
- Sign back in to iMessage and Facetime on your other devices.
Tap Settings > General > Reset > Reset Network Settings.
Use iTunes or iCloud to back up your content, then restore your device.
All the best.