I tried finding a date in 48 hours: The results

On Thursday afternoon, I spontaneously made a decision that flipped the last 72 hours of my life upside down. If you gain anything from the story, I hope it's the courage to say yes to a new experience today.

New to Los Angeles and tired of the same old mantra that dating in this city is impossible, I challenged myself to find a date to the LAWineFest in Hollywood. A Tinder Queen of sorts, the twist would be that I had to meet my date in real life, no dating apps allowed! 

I genuinely didn’t know what would happen and expected to fail miserably.

The five rules were:

  • My date to LA Wine Fest can't be someone I know
  • I must meet my date in real life (IRL), not off of a dating app
  • It has to be someone I would genuinely see myself dating
  • No referrals
  • If I don’t find a date, I still go and mingle

Being that I work a 9-5 copywriting job by day, Thursday evening would be limited for man hunting and I realistically had Friday to find a date unless I made some kind of magic happen.

As it turns out, I'm no magician and magic did not happen.


Thursday after work I headed to Philz Coffee in DTLA with a friend to catch up on a few writing assignments. There was a cute guy with a cowboy hat sitting to our left as we danced in our seats to the trendy music that seemed to go hand in hand with our carefree moods.

We chatted with the guys to our left about Reddit and politics until the shop closed. As it turns out, I’m no magician and magic did not happen. I didn’t find a date that night.

As Viv and I walked towards the Expo line, a guy that I’d been chatting for a few weeks on Tinder invited me to grab a drink. Desperately needing a break between myself and my computer, I accepted. The date went well, but he would not be qualified to attend LAWineFest with me, as I met him online.

On Friday evening as I was prepping to head home from work, I was invited to do something unique. The improv group Power up! needed someone on short notice to be involved in a 5-10 minute blind date on stage in front of a crowd. Naturally, my friends who came across the opportunity introduced me to one of the group members and all I knew was to meet at Westside Comedy Theatre in Santa Monica at 11pm. 

I arrived solo after a party for my rockstar friend who’s going into a major surgery as I type this. I saw a man sitting in the back row alone when I broke out my best pickup line and said, “Hey, are you sitting by yourself?” It turns out he was.

I sat down next to him and to my surprise, he couldn’t stop engaging the most incredible conversations. He told me about his past life studying to become a lawyer and current life as a cinematographer. I couldn’t help but fall in love in the moment. It's rare that I meet anyone half as open as I am.

The show began and before I knew it, I was being introduced to come onto the stage. In that moment I realized that I never even introduced myself to the guy in the back row, let's call him Chase. Chase had no idea that I had arrived alone, my name, or the fact that I’d be going up on stage.

After exposing random embarrassing facts about myself on stage, I sat back down next to Chase.

Power up! performed improv based on the date and after the show, I worked up the courage to invite my chair neighbor on a date. I told him about my challenge and invited him to the wine festival.

“I’m going to say the most LA thing ever but, from when to when?” he said. It turns out, he had an early shoot the next day. I feared he'd have to decline.

I exchanged numbers with Chase as we shared a smoke and agreed on a time to meet the next day. I went to bed on such a high.

Saturday morning, we went back and forth pushing our date time later and later. I was convinced the both of us would bail in typical LA fashion, especially as a migraine started to creep up on me.

A few hours later followed by the largest cup of coffee I could find, me and my date reunited in Hollywood. I kept a Stella-branded cup for the memories that I’ll probably creepingly put a rose in for the next few weeks to remember the feeling I felt when I just decided to say yes. Say yes to the wine festival, going on a blind date on stage, heading to the comedy bar alone, having the courage to ask this nearly seven-foot giant on a date.

It turns out, he was a beautiful humble giant.

We headed back to his apartment a few blocks away and continued to exchange stories. I thought the night would end there as he invited me to join him on an outing with him and his friends in WeHo. He wanted to go to a fucking club.

Now, for those of you who don't know me, going to a club is the bane of my existence. I moved to Los Angeles without makeup, let alone a pair of heels. Still intrigued by his personality I decided to join him and see how things panned out.

Dozens of people piled up in line outside of the club as Chase walked us to the front of the line. A few short years working in the bartending scene in LA and Chase had managed to become great friends with some pretty wonderfully hearted socialites. I couldn't help but be captivated by the layers behind his wonderful personality.

As the night began to unwind, my stomach started to feel heavy. The last 24 hours took such a wild turn of their own and ending on this high wouldn’t be ideal in the morning.  I’d trade his comforting arms for the comfort of my own bed. 

I gathered my things and headed back to my apartment on the Westside. I had a Tinder date lined up for Sunday afternoon followed by a Tinder Storytelling Show at The Lost Knight in Echo Park. I looked forward to performing and seeing the Undateable cast in the audience.

As I fell asleep I wondered, would my dating adventures take me back to the internet?