I am wondering if my friend received two texts being one was sent as text message but the next sent as delivered through iMessage?

I texted my good friend something today (I haven't spoken to him in 3 days he let me know earlier today that his phone broke & he had to get a new one) so I texted him one part of something I wanted to tell him the first text I sent I had to send as text message but the next text I sent was sent regularly through iMessages (we both hge iPhones) & it said delivered. So my question is, does anyone know if he received both texts despite the first going through as a Text message then 2 minutes later the next going through as iMessage. Because the second text by itself wouldn't make any sense if you don't read the first text