You can say he is full of it, manipulator, fake, etc. but Rob is showing how playing it cool and having some game goes a long way.
I am seeing Carlo, Rocky, Jay, Ussman, etc. make their first dates super awkward with random “Can I kiss you?” And “I don’t like you, I love you.” out of nowhere. It is bad enough as is for a first date, but even worse when it’s just the getting to know you phase and before any chemistry has developed.
And this is where Rob comes in. He waited for Jenniffer to see what a putz Cole was and when given the jet ski dare make her laugh and enjoy herself before smoothly hinting at making something more of their relationship. Sorry, but that is how it is done.