If I did this to him would this be OBVIOUS? I am scared?

What I got from this is, your friend haylee didn't like this matt guy, set him up, now hes kinda upset. So you sent a message to him saying the above to break the ice because you want to get to know him better... Okay... so this Matt kid was really into haylee and haylee didnt want matt. I think if you like him and want to get to know him better, by all means do! He may need some time to move on and forget about Haylee depending on how much he liked her... I don't think it would make it obvious that you know Haylee... Just try and get to know him better and see where it takes you.