Here are the Five Things I learned from Facebook Live Broadcasting my dates

Tales of Putrid Wi-Fi, Romantic Missteps, and Angry Uber Drivers

This logo started it all.

These comments were everything!

Folks (and not just my Facebook friends!) not only enjoyed my honest, relatable, even self-deprecating perspective on twentysomething dating, they even shared it with their friends!

I was fired up, and figured my path to blue checkmarks on social media, parties with Lil Dicky, and most importantly, epic romance was forged.

Unfortunately, it didn’t quite work that way and surprisingly, live broadcasting your date nights proved to be an unsustainable content strategy.

Who would have thought?

For those interested in broadcasting their own dating life (all the cool kids are doing it), I wanted to outline some of the key lessons learned from my experience with UpDATING.

1. Never trust bar WiFi.

This is me in the bathroom…mid-date.

The Halftime Report was the crème da la crème of the experience. Mid-date, I excused myself to go to the bathroom (with a smirk and “if only they knew face”), where I broadcasted an update to the Brunch Media Facebook page. What drink did she order? What is the vibe so far? Did I go for the hug or handshake? Problem is, the Wi-Fi in the bathrooms was incredibly untrustworthy. It staggered in and out, the picture became blurry, and most importantly, it prolonged an already sketchy bathroom trip. Little did I know bars de-emphasize Wi-Fi in select parts of the venue, specifically the washroom.

2. Details, details, details…

My commentary was playful, genuine, and sporadically spurred a Facebook comment filled with the desirable “haha” or “lol.” With that said, I did not “kiss and tell” at the level necessary to really make this a huge hit. As much fun as it was to tell the world about my date night, I could not possibly mention certain details, the bad, the ugly, even the PG-13 rated version (😉).

This is me discussing the texting game plan for the next dat.

After all, without permission from the date-ees, I was actually at risk of privacy invasion if I took the game too far. The most graphic detail I could muster to say on live camera for the postgame was the following: “the date went well…but not incredibly well because I’m waking up alone…here in my apartment.” Surely this mustered a few giggles, but unfortunately, if you have potential coworkers, family members, and other folks watching, it’s best to not disclose intimate details of your romantic life….although I couldn’t care less about strangers knowing if I rounded second base.

3. Uber driver permission.

This is me attempting to chat with Margot, my Uber driver.

That’s right, the pregame for the Live dates consisted of recording my pre-date thoughts along with a profound take on a specific dating concept (i.e. are more options better?) with an occasional jibe from the Uber driver. Needless to say, the Uber drivers were not too thrilled to be involved in my social experiment. When I asked if each Uber driver would be willing to be featured on camera, they all responded emphatically in the wrong direction. I was even charged a $20 fee for being a reckless passenger (don’t worry, he earned a whopping 2-star rating). Simply put, my Toyota Prius voyages to the main event of the night brought some sizzle, but not nearly enough spice.

4. Encouraging others to follow suit.

I opened my heart, my humor, and my sanity to the social media stratosphere. It was surprisingly fulfilling, so naturally, I wanted others to follow suit. One friend even went live with a pregame calling it her “Harrison Forman impression,” or as I like to call it, an ego boost. Problem was, beyond that, no one wanted in. What I failed to do was make it appealing to others not just to watch, but to share their own stories a la “Humans of New York.” I think the key with this type of social experiment is to tailor it in a way where it’s easily replicable. The format (super webby), the goal (disclosing deeply personal thoughts), and the mission (Rated-R) all were a bit over the top for Steve the Investment Banker in NYC or Rita the Social Media Specialist in Chicago to try. It would have made sense to initially grow a simpler concept.

This never actually happened.

5. Catch 22: impossible to find true romance.

By far the most important failure of UpDATING was the elephant in the room: what would my date think of my videos? Sure, I used witty puns to scold myself instead of my dates, and yes, I repeatedly praised her on some well-thought out conversation starters. Unfortunately, no accolade could diminish the shock of your finding your date (or potential date) running to the bathroom mid-date to record a Live update to his friends, and then seeing his review of the evening all over the Internet the next day. Needless to say, I was turned down by three separate women for dates after the first three episodes. They did not want to be “featured in the blog” as they called it. Their loss, I thought! Turns out, I put my empathy hat on and realized it would be impossible to continue dating someone with the internet knowing every single move along the way.

These comments made it all worth it.

Did UpDATING find me a winner? Nope. Did UpDATING overtake the Bachelor in ratings? Not quite. Did UpDATING reinforce twentysomethings about their own dating trials, tribulations, and experiences? Absolutely.

And yes, Guinness as a first drink choice on date one will raise a few eyebrows.

I only scratched the surface of the next level of authentic dating content. This concept can evolve a million ways moving forward (hit me up if you have any thoughts!), but the fact remains: I tried, I dated, and I failed to find love through UpDATING.

….but hey, at least I kind of, sorta, maybe, potentially rounded second base!

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