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I Went on 30 Dates in One Weekend (Yes, You Read That Right!)

“What do you like to do for fun?” is now a personal trigger

How is that even possible?!” My friend asked after I told her I couldn’t happy hour with her this weekend because I was going on 30 dates in three days. I’ll admit, this did feel like an impossible feat. But you know what? As I approach 32, single, and ready to date with clear eyes and a full heart—I can’t lose! Even if that means going out with 30 L.A. men who are more interested in their Teslas than with what I like to do for fun.

So, I redownload all of my dating apps and compulsively checked them like it was my job to offer my number—even when no one asked. I nixed the small talk and upgraded my conversations from “Hey, what’s up?” to “What are you doing at 8:30 AM on Saturday?” Aggressive? Maybs. Worth it? Totally.

I even made a google doc with pictures and phone numbers of all my upcoming dates to share with my friends (in case I got murdered or something)—and, okay, to also keep me on track so I didn't mix-up the boys. Here’s a breakdown of my 30 dates, and FWIW, names have been changed to protect me and these very fragile male egos.

Day One

Date 1: Friday 12:01 AM—Bob*

I wasn’t planning on my first date being a booty call, but Bob was in town. He and I have been Whatsapping (he lives in London) since January and had a decent first date in March, so technically we were celebrating our six month anniversary.

Date 2: Friday 8:30 AM—Mason*

This was my first breakfast date and 10/10 would recommend. There was no booze ordered (alcohol would make it brunch, and brunch never begins before noon), but we did have three rounds of coffee and delicious egg dishes.

Mason had his life together more than most people in Los Angeles do, and I’d totally grab breakfast with him again—maybe with a mimosa buzz this time around.

Date 3: Friday 2:30 PM—Tim*

In person, Tim looked more haggard than what his shirtless Hinge headshots suggested. When we hugged, he looked me up and down like I wasn’t “effortlessly sexy” which he said to me on the app. That was hilarious considering when he lowered his black Wayfarers, I saw the eyes of a man who looked much older than 29.

I excused myself after an hour, despite not having another date until 5:30 PM. I might not be effortlessly sexy in real life by his standards, but Tim was effortlessly the worst by mine.

Date 4: Friday 5:30 PM—Ian*

Ian called me after we matched for a pre-date phone call—cute! But over HH drinks, he told me: “Sucks how uptight everyone is these days, I really do a great impression of a black guy!” And that was… not at all cute.

I peaced out after our first round, but then watched him walk back into the bar—which, to my horror, was where I was supposed to meet Date Six in an hour…shit.

Date 5: Friday 6:30 PM—Max*

I didn’t realize when I matched with Max that we went on a date seven years ago. Oops! I guess that’s bound to happen when you’re aggressively swiping.

We bonded over beer and two separate orders of Pad Thai (he admitted he’s not good at sharing, I wonder what else that translates to...) and I couldn’t remember why I stopped seeing him seven years ago—maybe I need another date to find out.

Date 6: Friday 7:45 PM—Dan*

Dan was ten minutes early and I was fifteen minutes late, so he was finishing off his first old fashioned when I arrived (sorry, Dan!).

I was impressed to learn he was a stand-in for Christian Bale (Patrick Bateman *is* my type) and I ordered a second drink as he ordered his third. Then, he pulled out a breathalyzer keychain, which was a little concerning, but not as concerning as him agreeing to split the tab when I had one and a half rounds, and he, three and a half.

Date 7: Friday 9 PM—Issac*

As we sat on lounge chairs at an iconic Hollywood hotel, Issac did my astrological chart on his phone. Turns out, I'm a Gemini rising?

Later, he asked me what my book was about, and I explained it discusses my exes in my twenties. His face dropped as he told me, "I could never date a girl who talks about her exes,” and I responded “Well then, we can’t date because that’s literally all I do. It was so nice meeting you." According to him, that made me *such* a Gemini.

Date 8: Friday 10 PM—Evan*

Evan canceled thirty minutes before we were supposed to meet. Thank u, next.

Date 9: Friday 11 PM—Greg*

Greg was sweet and understanding… but that’s about all I remember from this date. I was fading, and mentally planning the snack I was going to eat when I got home. Crackers and hummus FTW!

Day Two

Date 10: Saturday 9 AM—Bryan*

Bryan bought me an iced oat latte as we walked, blinded by the hot morning sun. “How’d you get into the wine industry?” I asked, not expecting that would launch Bryan into a 40-minute TED Talk about his journey living and working in Los Angeles. He then joked that I could tell him my story on our second date—TBD on that one, bud.

Date 11: Saturday 10 AM—Bill*

Bill followed me on Instagram after finding me on a dating app, which is, well, weird… but I finally agreed to go out with him once I decided to do this challenge. He referred to himself in the third person, which he explained was because he’s left-handed (?!). Nice guy... for anyone else but me.

Date 12: Saturday 12 PM—Allen*

Allen and I went on two dates a few years ago. He was a personal trainer and a bit of a meathead at the time, so I was v happy to see him more mature, refined, and self-aware. Over chopped salads and iced teas, we caught up on where life had taken us.

I was impressed to learn Allen got into some science program (sorry I can’t be more specific, I space out when people talk about math or science), and he asked me on date number two. I’m looking forward to it as long as he doesn’t cancel after reading this article (Allen, for what it's worth, you were a cute meathead, okay?).

Date 13: Saturday 1:30 PM—Steven*

Steven and I bonded over dating app horror stories as we sipped our coffees, and I learned that our mutual friend who set us up used to date him. That was really all there was here...#Friendzoned.

Date 14: Saturday 2:30 PM—Sal*

Sal and I went on a handful of dates a few months ago, but I told him I’d rather be friends. We still text (mostly about The Bachelorette), so I asked if he’d be down to go on a date for my challenge. Over a bloody Mary and a mimosa, we caught up. I insisted on treating. I didn’t want Sal to think I wanted to romantically date him again—sorry!

Date 15: Saturday 3:30 PM—Daniel*

I felt energized by Daniel's presence as we strolled down the Hollywood Walk of Fame like tourists. We found ourselves at Dave and Busters, where I lost at pop-a-shot, car racing, motorcycle racing, and some “shoot the aliens” game (I’m not very coordinated).

While I’d be down to jump with Daniel while playing Dance Dance Revolution again, I don’t think I could picture myself jumping his bones anytime soon.

Date 16: Saturday 4:30 PM—Chad*

I was ten minutes late to meet Chad at a boutique chocolate shop, but he didn't mind. We sampled sweets, bought a few, and brought them to a dog park nearby. As pups frolicked on the green, we told each other our Hollywood stories. Then, I learned Chad’s divorce isn’t finalized, which makes me hesitant to accept his offer for a second dinner date this week.

Date 17: Saturday 5:30 PM—Oscar*

I was happily Oscar-canceled. I was starting to crash anyway, and needed some chill time before my 8 PM date. Not mad about it.

Date 18: Saturday 8:00 PM—Ken*

I was really excited to meet Ken, who was from the hometown next to mine. As I sipped my white wine, I was relieved to discover that our conversation flowed as effortlessly in person as it did on the app.

When he asked me for a second date over text the following Monday, I told him about this challenge. He said he was disappointed and wished that I wouldn’t include him in the article... so obvi, he’s included in the article. Ken, if you’re reading this, you need to calm down.

Date 19: Saturday 10 PM—Aaron*

I starting messaging with Aaron hoping for an impromptu meet-up. He suggested we go to a “serotonin-fueled dance fest in Hollywood” which I think translated to "Let's do Molly and dance" ?

This did not seem appealing to someone who had just gotten her period after being on nine dates, so we chatted on the phone instead—hey, it counts, okay?

Day Three

Date 20: Sunday 8 AM—Cam*

Cam and I went to the same high school and he was a freshman when I was a senior. Age shouldn't have been a big deal, but we felt decades apart on our hour-long brisk morning hike.

For starters, he gave me homework before our date. He asked me to list off my favorite movies including favorite comedy, guilty pleasure, animation, book adaption, top ten, and foreign films. I know, I’m exhausted just typing that. I did not do my homework, but if I were to name this date after a movie, it would be Gone Girl.

Date 21: Sunday 9:30 AM—Brian

Brian is a friend who was fascinated by this experiment, and offered to take me to the farmer's market to sample mulberries and melon for date twenty one.

His biggest contribution? He introduced me to Olive Oil Guy, who literally just reeked of sex (and olive oil). Olive Oil Guy said he’d go on a date with me, but I doubted it, because I saw he had 143 unanswered texts on his phone.

Date 22: Sunday 11 AM—Will*

Will is an Instagram friend I’ve never met who went to the same college as me. He’s also a neighbor, so he was excited to meet me for brunch at a spot equidistant to our apartments. We met at the same British gastropub I had my last date at on Friday and mimosa on Saturday. Best part of the date? I went unrecognized by my waiter.

Date 23: Sunday 12:30 PM—Andrew*

He canceled. Phew. I finally had time to shower after that hike.

Date 24: Sunday 1:30 PM—Dave*

Dave was a cancer survivor who speaks nine languages. He was intelligent, cute, and seemed into me...? He texted me on Monday asking if we could hang out again, and when I told him about 30 dates, he said it's “potentially a great how-we-met story if things go well.” Fun fact about me? I give a hell of a first date, but it’s all downhill from there. Wish me luck!

Date 25: Sunday 4:30 PM—Mike*

I was really looking forward to meeting Mike, as we had the strongest text game out of all of my dates. But, in person, he seemed more melancholy and low-energy than his texting game suggested. Did he, too, just go on 25 dates this weekend? Unclear.

Date 26: Sunday 5:30 PM—Johnny*

First round of drinks, and I didn’t expect to be as into Johnny as I was. Maybe it was because the other 24 dates ended with no more than a tight hug and low expectations. But there was something incredibly comfortable and sexy about him, which took me onward to Date 27…

Date 27: Sunday 6:30 PM—Johnny*

On our second round of drinks, I learned there is something very wrong with Johnny: He hates the golden years of The Simpsons, but loves Futurama and Family Guy—which, to me, is like someone loving pizza, but hating Italy. I was too distracted by my Peroni buzz and Johnny’s biceps to really get upset about this, though...

Date 28: Sunday 7:30 PM—Johnny*

I felt so comfortable with Johnny that I told him about the experiment. He was not only surprisingly receptive, but also wanted to keep hanging out. So, I canceled my dates with Olive Oil Guy and the Serotonin Sweetie. Until next week, boys!

Date 29: Sunday 8:30 PM—Johnny*

We went back to my place... He gave me a head start so I had time to clean up the makeup and clothes that were everywhere (you think getting ready for one date is difficult, try getting ready for 30!). We did a Prosecco toast to me and my 26 dates.

Date 30: Sunday 10:00 PM—Johnny*

Three hours later, we were still hanging out and playing our favorite songs for each other. Overall, I had those embarrassing butterfly things in my stomach I'd never admit outside of this article.

I hope I see Johnny again, but worry once he reads this, he’ll probably never want to see me again. Which maybe is dodging a bullet because what sociopath can’t appreciate the golden years of The Simpsons?!

Final Thoughts

Sure, this experiment was exhausting and draining, and yes, “What do you like to do for fun?” is now a personal trigger. But this social experiment—rather, my mission to find true love—was absolutely thrilling and worth every iced oat latte, happy hour white wine, and Uber of Pride.

Does this make me the next Bachelorette? Am I famous now? Should I start selling gummy hair vitamins on IG? Chris Harrison, call me! I’ll get hair extensions, I promise!