The vibe I got from the sexting is ‘no strings attached’ and the 'rolling through town’ which he clearly said to Ann Marie while a demon.
This whole thing, for me, isn’t 'the real’ Dean.
Not the 'rolling through town’ which was a demon!dean line, no matter who originated this.
Not the dating app instead flirting at local bars
Not the dragging Sam to 8 hours drive just to get hooked up.
Nothing. Nothing for me here is the Dean I know, not even earlier seasons Dean who used to sleep around a lot.