As mentioned earlier in the Bennifer post, the Jennifer Klein Day of Indulgence event happened this weekend in Hollywood and it’s been, in years past, one of the most coveted invitations in town. And while there is so much free sh-t to be had, and celebrities do leave with it, most of the quotes, at least in previous times, about the draw of the event, were about how they enjoyed the party because it’s a chance to catch up with friends, women in the industry connecting and reconnecting with each other. Also… getting free sh-t. Obviously the free sh-t part doesn’t sound so good in an interview though, but it’s still an example of how even the stars love not paying for things. Human nature!


What if you’re a new star though? Beyond the free sh-t, what’s the draw – and what’s the experience. That’s what I’m thinking about where Olivia Rodrigo is concerned, arguably one of the biggest names to emerge in 2021, with one of the biggest songs of the year, on one of the biggest albums of the year, and what’s expected to be a big career ahead of her. She’s currently on the cover of the Young Hollywood issue of Variety, alongside Lil Nas X, and everyone is paying attention, even outside of the music industry. 

So she made the guest list for the Day of Indulgence, showing up in a really cute outfit wearing a pair of badass stompers. I’m curious, though, if this is an event that brings women in Hollywood together, who she vibed with while she was there. What new other celebrity connections she made. Olivia is closer in age, for example, to Emme, JLo’s daughter, who accompanied her mother to the party. Did JLo make the introduction? Did other celebrities with teenage children, like Leslie Mann, approach Olivia for a photo for street cred with their kids? 


What’s interesting about Olivia is that even though she’s of the TikTok generation, she’s much less active on social media than her contemporaries. Which makes her almost an outlier. Lil Nas X’s superpower is social media trolling – no one has been better than he has been in leveraging momentum from multiple platforms, and using it to both empower and antagonise. Olivia, however, has chosen to remain detached from social media, prioritising her mental health, and while there’s no one right way to go about it, and people have to do what’s best for themselves, it means that Olivia has kept her public and private circles quite contained. Anastasia, who is of the same demographic, writes often about relatability, and the key to success with the younger generation, a major part of that being social media engagement – choosing accessibility over mystery. Yet here we have one of the generation’s most promising stars kinda playing in a lane that feels a little old school and thus more of an enigma than you would expect of someone her age. 

I was surprised to see her show up on the list of names at this party. And I have no idea what party she might show up to next, aside from the standard ones that are expected, like the VMAs in a month. This is a good thing. Already she’s unpredictable.