I Used to Make Penis Hats for a Living (and Other Things I’m Embarrassed to Tell You)


I have something to admit.

I’ve fudged the facts of my story.

Let me explain. I just saw Daniel Radcliffe in a play on Broadway. As you may have guessed, it was magical.

The play was about a writer who altered the facts of a story for a bigger impact and a fact checker who took him to task on every single inaccuracy. It was like a Battle Royale, truth edition.

Even though the facts were not on the writer’s side, I was.

I relate to this character a lot because I know first hand that control of a story can be a beautiful thing. And when we want people to see a story (or us) in a certain way, omissions here and there seem ok.

Here’s why it relates to me: I’ve been hiding some of my story. I’ve been hiding for fear that my weird path disqualifies me from owning my knowledge and living my current dream.

But I’ve realized that my winding story is more important for you to hear than the one I think is prettiest.

I want to show up fully for Brazen and for you. And that means sharing some things that don’t make sense on my resume.

1. I moved to New York to pursue musical theater… and it didn’t go well.

As a kid, I would listen to the Hairspray soundtrack in my room and cry, desperate to be pony-ing onstage to “You Can’t Stop the Beat.”

After only a year at my first “adult” job on the West Coast, I quit and moved to New York to pursue my childhood dream of being on Broadway. I had no friends, no place to live, no job, with little theater and voice training. I was unskilled and determined to make this work.

A few times a week, I would wake up at 5:30 am to go wait in a line so long that I might not get into the audition room. Tensions and stakes were high.

I got a few small shows in the two years I was working at this, but line after line, my heart was yearning for more purpose, direction and control. As hard as it was to admit, this dream and particular hustle wasn’t for me.

2. I used to make balloon hats for a living.

Yep, really. This was my job before starting my matchmaking journey.

I was in New York, broke, no job prospects and stumbled into this under-the-table, only-paid-in-cash-tips job at the Senor Frogs in Times Square.

For those of you who don’t know what restaurant I’m talking about, the New York Times called it “Spring Break Forever.” Equipped with giant margaritas, constant strobe lights and blaring music.

I would work late night shifts, twisting balloons into flowers, monkeys, swords and (after 10pm) penises.

Honestly, I cleaned up at that job, night after night. I was making more money than I had ever before.

But (and it’s a big but) yelling over the clubby music to ask for a $3 tip was wearing on me. And I was having anxiety attacks in the back on the reg. Not good.

I didn’t last. Neither did Senor Frogs Times Square. RIP.

3. I don’t like the professional dating space.

When I began matchmaking, I didn’t know what I was getting myself into. I thought it would be a fun, easy job. I was wrong.

Through dates that went terribly wrong and hard conversations with clients, I learned that dating is a microcosm of every vulnerability, insecurity, fear and hope that we have in life. Talk about high stakes.

After setting up hundreds of clients on hundreds of dates, I looked around the pro dating landscape at coaches, matchmaking services and the like, and I realized that a lot of this world runs on “shoulds” and “shouldn’ts,” “don’ts” and “I know better than you-s.”

The whole thing seemed pretty disempowering. And as someone who thinks that conventional dating wisdom is generally unhelpful and that women know what they need to be most successful, I was frustrated and didn’t know if I could make a difference in this industry.

I felt led to create the space I yearned for, to be a respite from the sometimes judgmental dating “shoulds” and “shouldn’ts” and to help women sharpen their instinctive dating toolkit so they feel amazing about themselves and date like it.

Because dating can sometimes feel like having an anxiety attack in the back room of Senor Frogs. Overwhelming, difficult to navigate and scary. But I know that it doesn’t have to.

I’m here for you. To bring honesty, support, gif searching ability and guidance to the pain points and joys of your love life.

Showing up fully is hard, especially because some parts of our story don’t sound as good as the glossy one we want people to believe. But it’s worth it to create a community that is strong, vulnerable and vibrant.

Now two questions for you.

What are you scared to share with people for fear they won’t take you seriously?

How can you show up with your whole self today, at work, on a date?

Answer in the comments below, I’d love to hear from you.

Lily WombleComment