Many years ago, I worked for a Senior Vice President of an insurance company. His name was Jack. He was a legend, a fatherly figure, and a self-proclaimed matchmaker. He lived and worked on the west coast. I was his human resources manager in Chicago. Jack would summon me to Seattle for meetings that were really just expensive dinners where he repeatedly said things like, “Why are you single? Are you pining over an ex-boyfriend? You’re too good for that.”

Back in the day, it was only inappropriate when guys like Jack propositioned you—and maybe not even then. In this case, he was reading me like a book, sensed my loneliness, and wanted to be helpful. He had a list of ten people interested in having dinner with me. Would I consider any of them?

I said no.

But one of the men on the list was his direct report named Dave, the insurance agency’s divisional Chief Financial Officer (CFO). The guy was newly divorced, in good shape, and liked animals. How is that not a good match for me?

“Does he have kids?” I asked.

He did. One boy. “He isn’t weird,” Jack added.

The boy or the kid, I wondered?

I declined the date because the whole thing sounded like trouble. Who needs more drama when you’re in your mid-20s, hanging on to memories of an ex-boyfriend, and wondering how you’ll earn enough money to pay rent, make good on your bills, and help some of your family members take care of themselves?

One day, Dave was in Chicago for CFO business. He popped into my office, introduced himself, and asked if I wanted to join him for dinner. I’m not going to lie: this guy was actually handsome and fit. How often is a description accurate? These were the days before Zoom, so I was genuinely stunned. I wasn’t sure how to ask if he liked cats and dogs, but I was totally into the idea of a meal on the company’s dime.

Like a dork, I said, “You had me at ‘free dinner.'”

We picked a local restaurant and decided to grab a drink at the bar. I ordered a Cosmopolitan (a vodka concoction that’s more cranberry juice than alcohol) because I thought it made me look rich and mature. He ordered a beer. After two drinks, we still hadn’t been seated, but we didn’t care. Dave regularly leaned into me to “talk over the noise,” and I remember asking to sip his beer.

At one point, Dave said, “I’ve just got to say it. Jack told me you’re very pretty, and he was right. Can we switch places so I can see you better?”

I was like, “I’m sorry, to see me? Do you mean hear me better?”

He said, “No, to see you. I have a prosthetic eye.”

I said, “What?”

Dave, who seemed familiar with my drunk and insensitive reaction, said slowly and loudly, “I am blind in one eye. I can’t see you when we’re seated like this. Can we please switch seats?”

And I’m like, oh my god, what is happening here? A man just called me pretty, and of course, I made a weird comment about his disability. So, I popped off the barstool, switched spots with him, and said, “I’m sorry. I’m having a great time. Thank you for asking me to dinner.”

We recovered, ordered food, and definitely had more drinks. Was Dave intoxicated? I have no idea. Was I drunk? Totally. Completely. Hammered. I was drunk even before the eye incident.

Dave kissed me in the parking lot and told me to email him when I got home. Yes, email, because this was in the age before mobile phones.

The next day, I had a return email that thanked me for the fun night but broke the bad news: Although Dave had fun, it didn’t feel right. Newly divorced, he had to focus on his son. But he enjoyed getting to know me and hoped we could continue to be colleagues and good friends.

I also had an email from Jack that said, “I’m proud of you, kid, for trying.”


I don’t regret the evening, and I certainly don’t regret kissing my client. Honestly, HR is fake. It’s not my company. And I’m an adult who can make my own choices and deal with the consequences. Where’s my HR? Why wasn’t someone there at dinner handing me drink tickets? The answer is that I don’t need it, and neither do most of you.

However, this encounter with Dave serves as a personal reminder of how alcohol can blur judgment and turn even the most well-intentioned and promising evenings into a comedy of errors. How often have I found myself in these absurd situations, reflecting on private or public confusion I’ve caused thanks to excessive drinking? Too often, for sure.

Blaming vodka for my social mishaps would be too easy. Being awkward is part of my brand, but it’s also a reflection of my choice not to learn how to improve my coping skills when I’m anxious. Yet, despite the slip-ups, I’m now committed to embracing authenticity and fostering genuine connections, even if it means trading in my Cosmopolitan for a glass of water at business dinners. I don’t always make that choice, but I’m better now than I’ve been in the past.

So here’s to forgiving ourselves (I mean, myself) when we insult someone with a prosthetic eye, hoping that they forgive us (fingers crossed), and raising a glass—with alcohol or not—to the messy, beautiful chaos of being human.