One of the main characters in questionable decisions, which led to some juicy Gossip Girl blasts, Lily’s screwups really seem to stand out, even all these years later.
From being ashamed of her children and lying just to look good in her friend group to sending an innocent man to prison, Lily continuously did things, such as the 10 listed below, that made it hard for her fellow characters and for viewers to always like her.
Lied About Eric’s Suicide Attempt
At the beginning of the series, Eric was in the Ostroff Center, due to trying to take his own life. And since the van der Woodsen family was an affluent and influential one, Lily tried to cover this up by telling everyone that her son was actually visiting her sister, Carol, in Florida.
Additionally, she tried to keep him in the center for as long as possible, to avoid dealing with the issue and out of fear of what he would do next.
Did Not Handle Eric’s Coming Out Very Well
Next in Eric’s story, he came out as gay, and Lily did not handle this news very well. Granted, Eric was outed in a not-so-nice way by Georgina Sparks, who was known for her manipulative behavior, but still, he took Lily’s shock as a sign that she did not care or approve.
Thankfully, after talking with Rufus, Lily came around and told Eric she loved him.
Slept With Rufus The Night Before Marrying Bart
For most of the show, Lily went back and forth between Rufus Humphrey and Bart Bass; she had loved Rufus for years, but she ended up engaged to Bart.
However, the night before the wedding, she went to one of Rufus’ concerts and then slept with him.
Hid Rufus’ Son From Him
Back in the day, Lily actually got pregnant with Rufus’ baby, but this was another part of life that was swept under the rug. She never told Rufus about it, and she gave the baby up.
Therefore, when this child, Scott, was eventually revealed, some issues and arguments arose.
Was Not Honest With Her Family
More mistrust came when Lily lied to Rufus about where she was all summer. It turned out that she was with her ex, William, and then she told everyone that she had cancer and was with him to get treatment.
That whole plotline was hard to keep up with, as no one was sure if she was really sick or if William was really helping her or not. Nevertheless, why would she keep such major information from her loved ones?
Had Serena Committed
Serena ended up at the Ostroff Center, as well, thanks to Lily. As soon as this mother even heard whispers of Serena doing drugs, she had her daughter involuntarily committed.
She did not think to stop or ask questions, and even after Serena tried to explain the truth, she would not believe her.
Sent An Innocent Man To Prison
Perhaps the worst thing Lily did involved Ben Donovan. This man was once one of Serena's teachers. In fact, he seemed to be Serena’s favorite teacher. One day, Lily went to Serena’s school, heard some students gossiping about Serena and Ben, and basically used the rumor as leverage to get what she wanted for said school.
The gossip led to an investigation, and Lily forged Serena's signature and sent Ben to jail for statutory rape.
Went Against Her Husband (Again)
Another complex storyline came about when Ivy pretended to be Lola and attempted to steal from this well-off family. First, Lily worked with William to get her home back. When that failed, Rufus came up with a plan, and Lily pretended to go along with it.
Long story short, she lied to Rufus, yet again, in order to get her material items and apartment and money back, which led to Rufus leaving.
Got Her Sister Arrested
Lily seemed to just love sending people away, including her own sister. As part of the Ivy story, it was revealed that Serena’s actual cousin, Lola Rhodes, was William’s daughter, as he cheated on Lily with Carol.
This led Lily to actually paying Ivy, after everything she did to try and avoid that, all so that Ivy could tell the police about Carol and have her arrested.
Interfered With Serena’s Proposal
One of Serena’s love interests on the show was Steven Spence, a man that Lily slept with once upon a time.
That was bad enough, but it got worse; he went to Lily, to ask for Serena’s hand in marriage, and Lily said she didn’t think Serena was ready for that step in life (info that had been put into her ear by Blair).