iPhone not receiving texts from my Android

[awsomsauce]

So my boyfriend just switched from his family's Verizon plan to my T-Mobile plan on Sunday 8/2. He brought his number, and also switched from Android to iPhone. Everything was peachy until earlier today, when his phone stopped receiving my texts. He can text me and anyone else without issue. I can text anyone else without issue, it's just his number that my texts get stuck on "sent", but he never receives. I've tried resetting both phones, resetting the network settings on both phones, toggling iMessage on his phone...I'm out of ideas. Anyone have any other ideas? Or do I need to hit up T-Mobile?

 

[BreakingKayfabe]

I have to ask, has he attempted to text your number? Sometimes when a message thread isn't deleted and a user switches to iMessage after being on SMS for very long, it takes a few attempts for the new iMessage user to establish the thread as iMessage.