I Went Home with Jeremy Piven: A Cautionary Tale

In light of the new Entourage movie I thought I would share a story of something that happened almost exactly 5 years ago on my first trip to LA. The whole reason why I live in LA is because of my best friend Annabelle. We met in high school and then were living in separate places for a while and at the end of my time in grad school she decided it was time for us to both live in LA. I had never actually been to LA before so she flew me out in June 2010 for my birthday present and we stayed at The Roosevelt Hotel and had quite the adventure. One of the fun touristy things to do when you’re in LA is to get tickets to be in the audience for a late night show. We decided to get tickets to The Tonight Show with Jay Leno on back to back dates because of the guests (the first day the guest was The Situation and I’m not going to get into why we were interested in seeing him in this post since that is a whole other story and the second day the guests were Jeremy Piven, Drake, and Louis CK). FYI if you want good seats at a show like this the secret is to dress up. The first day we were picked to sit in the front 2 seats and we made friends with someone in the band who got us out of waiting with the crowd the second day and instead we got to wait in the green room with a few of Drake’s entourage who stared at their phones the whole time and we were seated back in the front 2 seats again.

Annabelle Jay Leno Lindsay June 2010
Here’s a blurry Blackberry photo of a Polaroid that was taken on our first day visiting the show. Remember it was 2010.

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My First Grouper Experience

When I first heard about the concept of Grouper I was intrigued, but instantly was turned off by it. Grouper is a social club that sets up drinks between 2 groups of friends: 3 guys and 3 girls. I immediately thought, but what if the guy I like likes one of my friends? That always sucks when that happens! You also get no choice as to who you are set up with so it’s a totally blind group date (except you know what your 2 friends look like because you invite them). You also have to pay for Grouper and I have never used a dating site I had to pay for. Grouper costs $20 per person plus a 10% tip for your server which covers their introduction and concierge service and a free first round of drinks at the bar they select for you (the concierge part).

Grouper is actually not claiming to be setting you up on a date and people who sign up don’t have to be single (but God would I be annoyed to go out with a group of guys who were all in relationships wtf). They are planning a night for you with the perfect girl to guy ratio and giving you ideas on how to make it fun. These ideas include preparing “two truths and a lie” before the date for a fun discussion or playing the iPhone game “Phrase Party”. I will say that going on a Grouper definitely takes a lot of the pressure off of the conversations you’re having and you feel less like you’re on a job interview and more like you’re hanging out with friends which is nice. Going out with friends also forces you to be a more authentic version of yourself because your friends might call your ass out or tell the embarrassing stories you might have tried to avoid which does help you get to know each other much faster. It also forces you to actually make a plan instead of getting stuck in chatting or messaging back and forth purgatory.

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