On Lily Van der Woodsen

high ramblings

Lily is just like such a good mother… but only to Chuck. She was generally a horrible mother to her actual biological children, but her step child? Arguably the best, most heartwarming relationship in the whole show. I feel like it’s the internalized misogyny and homophobia.

She sees too much of herself in Serena - a constant party girl with a string of bad romantic decisions and a problem with alcohol. Lily doesn’t even accept herself as a person, so how can she ever be expected to accept Serena? I think you could argue she didn’t really want a life like this. It was established that she was a pretty accomplished photographer and had her work published in magazines, but CeCe wouldn’t fund her because she didn’t approve of her bohemian lifestyle. You could argue CeCe was the one who made the decision, but I think it was Lily. She obviously chose Will over Rufus, the wealthy man her mom approved of over the struggling musician.

It’s unclear what the timeline was, how long between her and Will getting together and Serena being born? How much time was between Rufus and Will, was there overlap? Rufus and Lily’s son was born approximately a year before Serena, since it’s established that he’s a year above the core group in his arc with Vanessa at NYU. It’s reasonable to assume that there was a short time between relationships.

But ultimately, Lily chose to return to the cushy life she grew up in. The millionaire over the rockstar. She continues her life of social climbing. She watches Serena grow up, growing more unmanageable everyday. Not unlike her mother who’s younger self we get a glimpse at as she drops out of boarding school and joins her sister in LA - cold, detached, with a general air of not really caring what her daughter does as long as it doesn’t cause her too much of an inconvenience. Serena is poised at the same ledge that Lily found herself in: she could choose a romantic life with the artist or her affluent life that she had been raised in. Serena had no shortage of wealthy Upper East Side men that she could have married, but continuously returned to Dan.

I think Lily knew Serena wouldn’t survive a life of not-luxury, she saw the weakness in Serena. To an extent I believe that Lily never was truly proud of her. Lily wanted to use her as a choose-your-own second life adventure. Lily herself had chosen the so-called comfortable life, hopping from rich man to rich man with no real connection to any of them, hosting various galas, serving in various social clubs and organizations. She is the ultimate society girl grown into society woman. And she’s unsatisfied. Her focus is mainly on getting her daughter out of situations, but you can imagine her thinking about what could have been.

What could have been not if she chose the rockstar over the rich doctor, but if she chose herself. Chose to follow her passions. Be known for her work as herself, but instead is now recognized by Mrs. Most Recent Husband’s Surname. Lily is a resilient woman, stronger than her daughter, her sister, and her mother. If she couldn’t escape the charmed life, none of the Rhodes women could. She can’t swallow the bitter pill of her life not turning out how she thought it might. Serena, however, can. Perhaps just a victim of her environment, Serena seems to have never fully developed any passions or hobbies beyond underage drinking and dating questionable men. She has never known anything besides a comfortable life, so she has no idea what life can be other than that.

As Lily perpetuated the cycle of sheltered wealthy daughters, Serena was never raised to be a strong person. Perhaps Lily knew that it was futile to raise a girl who would be independent in that Upper East Side world, maybe it just became a self fulfilling prophecy. Regardless, Serena became a petulant, flighty woman who is doomed to follow in her mother’s footsteps of husband hopping. It was never any use expecting to be proud of her daughter.

She loved Eric, but in the way you’d love a stuffed animal. Or better yet Birkin. An accessory. One that she had to keep perfect but unfortunately Eric would not just stand there and be seen and not heard. He had to go off and have an untreated mental illness (could not be a result of his childhood) and then be gay. Unfortunately, the concept of gay son and thot daughter hadn’t been discovered yet. Lily has more patience for Eric, but still the same lack of genuine warmth and interest she has towards Serena.

Which leaves Chuck, the sociopathic, death-faking ex-husband’s son. Whereas in Serena she saw who she actually was, Lily saw who she wanted to be in Chuck. He had the drive and ambition Serena lacked and Lily couldn’t nurture (or force) into her. She saw Chuck as a worthwhile investment, a child she could be proud of. Someone who would unconditionally adore her. Lily saw a kindred spirit in Chuck - under supervised, over financed, with both a healthy dose of mommy and daddy issues. Chuck represented what she could have been if she had chose herself, if she as a woman could have the same success and ability to choose herself.

Lily struggles to love herself, so she choose to love Chuck for what she could have been.