Most Helpful Guy
It depends on how important him paying is to you. Coffee is cheap, he might spring for the check after a meal but think nothing of you paying for a coffee.
At this stage I'd focus more on whether you enjoy spending time with him and whether there's any chemistry, then worry about smaller details like this if you continue seeing each other.
Most Helpful Girl
It was rude that he ordered his own coffee before you arrived then to just let you walk over to order your own! He should've waited for you to arrive before ordering his, then ordered both your coffees and paid for both of them. I wouldn't see him again if I were you.