So if she is 19 in this pictorial and its July 2002, Then the current game is set in 2021? ( she is 38 and thus born in 1983).. Assuming as I have seen it written in previous posts that Ellie is 18 (+/- 6months) That would mean Sophia had her when she was 20 which could mean she is pregnant in this photo?...

.. I have always thought she should have been made to be a few years older..
I'd say stating the date is a slip. When a VN takes years for completion it gets convoluted over the course of time. Time dilation works pretty bad for this sort of things.
It's not the worse thing, though. He's sticking to a cliche of coercing his MC into submission either through guilt, "educational purposes", blackmail or expanding her son's horizons.
What has happened to her maternal and not so much feelings towards him, if we compare very similar path on Ellie's side? They both playing mind games with their mom, yet L&P makes look Dylan's approach more headlong and rash. Sam's storyline seems more coherent at this point. It's based on a mutual affection, not twisting the arm. Anyway, part I is only an appetizer, ending with the usual and annoying cliffhanger, for the part II, the real deal. If, somehow, by the end of PII Sophia or both of them get naked, it'll be a huge step towards smth spicier the very next PD. BTW, the kiss is a must during these events, without it the whole mother-son quality time loses it's charm.