I agree with majority here, this Jessica route just seems off for both Chris and Dana's character arc.Maybe I'm missing some point here with Jessica.I would like to point my view on this, I maybe go little to brief on this so please bear with me.
It's stated the Dana and Chris were kind in love with each other as long as they could remember. But because they being sibling they were forced to keep there feeling bottled up due to social hokum the incest is.
Until now i.e the timeline the game captures. Both are now adults here both having their fair share of relationship, each falling apart as there inner self subconsciously wanting each other. They crave for each other not being able to tell it to each other, but still they both can feel that spark.
Chris being a playboy was obviously had he's fair share of women, he was a spoiled brat, may he was frustrated to the fact that the only girl he wants in his life is finger nails away from him yet he can't have her(And yes I mean in a romantic way and just physical). This also explains him get his act together (Not screwing around, coming up drunk in office, and causing other nuisance his father stated he used to cause before)as soon as starts getting closer to Dana.
Then they try out this "Dates" with this characters in game i.e J, A & M+J,
The way I see this
It's a hoax they both create subconsciously to get close to each other. Then after third date they could not content this spark and sort the wildfire on weekend gateway.
Here's the thing now that I disagree gomly1980 completely, yes Chris was a Dom, yes he was a playboy but One thing is for sure is love for Dana is unconditional and whatever pleases her he will make do with it. If Dana would have not a problem he would marry her right then and there.
All this beard plans are to make amends with Dana's fear of public opinion on their relation.
He does not want Andrea-Maria all those past relation(before he had any hope to have relation with Dana) It's all he his doing to keep dating dana as she is to afraid to get caught.
He is not selfish If it were upto him He would go "Dana Only Path Himself"(Man I wished there was a Dana only path).
But the reality hits us hard (Dana gives this story the anchor point to which this game universe establishes anchor with universe we live in, giving the realism we all cling to and love )and we go ahead with this bread plan.
DO NOT MISTAKE THIS AS CHRIS'S EFFORT CREATING A HAREM FOR HIM SELF. He is just trying to make Dana comfortable here.
From what I observe in Maria and John path Chris is happy as he get to fuck around (because he has this hormone crazy dick of his) but Dana is a little uncomfortable with john but Is ready to compromise for the sake of Chris.
In Jessica path Dana is happy as she get's her oldest best friend to be part of rest of her life. Why would she not be happy Ask any girl in real life If she could spend rest of her life living with her BFF and they would go crazy. My point being any girl on world would love this setup but Chris has to compromise in this cause the this Jessica domination thing is not his ARC but he will make do for sake of Dana.
To me Andrea path is the only path in which both Dana and Chris don't have to compromise. Yes If Chris goes in "Bad Daddy path" it does looks like he is acting a little selfish but in "Good Daddy path" he and Dana are actually caring for her like their own.
Just because there is no Dana only path, IN MY OPINION Andrea path seems to fit the arc fit the story the most.
P.S- I have a every special spot for the way this game has gone till now, and Jessica path is not my taste, I did go on first date as it was mandate but could not handle more of her. This gateway would just ruin my view on the game so I with all due respect to others will not go on that play this path, I haven't done M+J path yet too.(Saw renders, looked to script in notepad++ but had not tried both these path and would like to keep it that way)