I got the Love Lost ending, like many people did. I found the game deep in its story design. Especially on its commentary on marriage. Did you notice how when Harry was "home" that he was greeted with pits, monotonous staircases, hallways, and room loops? This is the endless cycle of the modern human relationship put in the context of a game level.
In general, the game was filled with symbols calling out Sigmund Freud's work.
The Dahlia character represents Cheryl's sub-conscious sexual feelings toward her father.
Most people seek and model their partners after their parents on a sub-conscious level, thus Cheryl's 'avatar' Dahlia lusts Harry and claims him as her husband.
In one of the final cutscenes of the game, Dahlia states "I am the lady of your life... Your salvation and your curse." She is not referring to a soul mate or marital connection. She is telling him that she is his daughter... the one true lady of any father's life. A connection to the future and the burden of the present.
Thus when Dahlia makes love to Harry on the boat to the Lighthouse, it is an incestuous consummation of sorts, but is really just how Cheryl models her sexual encounters with men in general. Booze and easy times...
Lisa, Cybil, and Michelle are obvious references to Sigmund Freud's psychological models and are thus the avatars of Cheryl's Id, Ego, and Super-Ego.
Lisa is the ID as she is the 'self-medicating' professional. Her role is to provide to Cheryl her natural instincts, but is completely horrible at this, as Lisa is not well put together and ends up 'dying' by her own negligence. This explains Cheryl's stealing sprees and reckless sexual behavior.
Cybil is the Ego. The watchdog of the ID. Her job is to ensure that the ID is stable so that Cheryl is protected from her guilt. Cybil's role is to literally police the chaos in Cheryl's mind...to detain Harry and to keep him from harming Cheryl. Her aggression toward Harry is an attempt to censor him from Cheryl.
Michelle is the Super Ego. Little Miss Perfect. Michelle strives for moral perfection in her role as the Super-ego, but also fails. Michelle seems perfectly OK with breaking into places and cannot hold onto John (the embodiment of security), the man that she loves most. In other words, with Michelle as the Super-ego, Cheryl's moral standards are very low, causing the lack of distinction between right and wrong.
Then there is, Dahlia, who is also a manifestation of the Super-Ego. Why do I come to this conclusion? Dahlia literally takes Michelle's place in the night club, suggesting that they are the same entity. In Cheryl's mind, perfection is her father's love and approval, thus Teen Dahlia represents an immature sexual perfection that might garner her absent father's approval... Wife Dahlia likely represents a feeling of unworthiness or abandonment left in the wake of Harry's divorce... A loving family that is abhorrent to behold for Harry.