Good Morning iselaaa,
Has something changed recently on one of your devices? If you are having an issue sending to only one contact (your boyfriend), follow the steps below. Your boyfriend should follow similar steps for his Samsung phone.
If your messages aren't sending, or you aren't getting messages
Check your contact information:
Make sure that you're using the right phone number or email address for the contact.
Go to Settings > Messages > Blocked and make sure that the contact isn't on your block list.
If messages won't send to a certain person or you need help with group messages
Sometimes your messages won't send to a particular contact, or you might have issues with group messages. For example, you might reply to a group conversation and receive your own message. Or you might get a new phone number and see your old one listed as a recipient in an existing group conversation.
Delete the conversation* that has the issue and start a new conversation:
*When you delete a conversation, you won’t be able to recover it. If you want to save parts of conversations or their attachments, you can take screenshots. You can also touch and hold an attachment or message bubble, then tap More > Save.
Open Messages and look at your list of conversations.
Swipe from right to left on the conversation you want to delete. Then tap Delete.
Open Messages, tap , and enter the phone number or email address of your contact or contacts.
Write a new message and tap send.
Restart your device and check for updates
Restart your device.
Check for a carrier settings update.
Check for an iOS software update.
Happy Holidays to you!