How to get a guy to flirt with you? I sent him a LinkedIn message

Last year, the nonprofit I work for went from requiring employees to come into the office twice a month to three times a week. I was upset with the change. It’s not that I don’t like the people I work with. I really do. It’s just that, especially during rush hour, I’m not a big fan of the 101 and 405 or alternate canyon routes. On top of that, I have an elevator phobia, and our West LA office is on the ninth floor. (Kudos to the kind and wonderful security guard who rides up with me most mornings.) But good things come to those who do return to the office, along with camaraderie and free snacks. We’ll call him J.

A few months ago, some new tenants moved into the office right next to the elevator on our floor. It looked like an office of young guys, lots of them, but too young for me. Many of them didn't look much older than my 19-year-old son.

One day I saw J waiting for the elevator. I was just passing through, but I liked what I saw: a strong jaw, a bit of stubble, broad shoulders, and the unmistakable curve of his biceps under his shirt. J was older than the younger guys. There was something else. Out of the corner of my eye, I noticed he was also looking at me as I walked away. I understand that not all women appreciate this kind of attention, but a few years after a divorce, I am single with a capital S. I liked the feeling, at least in this case.

I saw J in passing a couple more times. He seemed nice, but I'm not very good at picking up or giving off that kind of vibe: the “I'd like to get to know you better” kind. I'm not sure what the heterosexual equivalent of gaydar is (“straightdar” doesn't sound as nice), but I'm pretty sure I don't have one.

One day, while walking back to my office with my older dog, Loki, who comes to work with me, I ran into J. I don’t remember exactly what he said to me, but he was so sweet to my pup. He knelt down to pet him. A guy who is cute, has a job, and is nice to my dog? I’m not saying he’s necessarily the holy triumvirate, but he’s pretty cool. Who was this guy? I wanted to know his name. Since most of the offices in our building, including J’s, have a plaque outside with the company name, this didn’t require any complex detective work. I found him right away on LinkedIn. I was just happy to have a name. I had no further plans.

A day or two later, late at night, past my usual bedtime and apparently past the time for my inhibitions, feeling like I had nothing to lose except my pride, I decided to do something out of the ordinary: see if I could send J a message. I went back to LinkedIn and found that I could send him exactly one message, even though we had no mutual connection. (Without a response from the recipient, LinkedIn informed me that my message would basically be dead on arrival.)

My subject: Daring question. My message: “Hi. I work on the same floor as you. I’m the woman with the crazy curly hair. Do you want to go for a walk or grab a coffee or drink sometime? I’m not in the habit of doing this, but you’re cute and seem nice. If you’re not single, I hope you’ll accept the compliments and ignore the rest. Leslee.”

I hit send and immediately had two distinct reactions. One was the equivalent of “Go ahead, girl!” The other was pure horror. What had I done? What was I thinking? I imagined him opening the message in his office and reading it out loud to a group of twenty-something colleagues. They would all know exactly who I was, every single one of them. It wasn’t exactly a Hester Prynne situation. Anyway.

A day went by without a reply, and I came up with a new situation to worry about, one of my specialties. How was I supposed to know if he had received my message? No reply meant one of two things: he hadn't received the message at all, or he had received it and had decided to ignore it. I wanted some reassurance about the first possibility. But even if I could find a way to send him a follow-up message (or, horror of horrors), I was forced to ask him in person if he had received my message, and he had, in fact, received it but had been indifferent, then I would look even dumber.

But that wasn’t what happened. The next morning I received a short, flirtatious, but entirely appropriate message from J on LinkedIn.

From there, we started texting. “Good morning, Leslee. This is J from the ninth floor. How are you this morning?” it would begin. A few days later, we met at Teaspoon, one of the many boba joints on Sawtelle Boulevard.

Toward the end of our time together, he put his elbow on the table and held up his palm. I thought maybe he was challenging me to arm wrestling. Did he know I used to beat all the boys in elementary school? He asked me to put my palm on his. He made sure I agreed. I didn't hesitate. It felt good.

Since we both prefer to keep our work and personal lives separate, neither of us necessarily wants our coworkers to know about this, whatever it is, which has led to some exciting and fun moments. J and I understand that this isn't a happy ending story, but it's been a lot of fun. I'm glad I decided to give it a try, in my own mild way. As J wrote in his LinkedIn response, “Fortune favors the bold.”

The author is a Los Angeles native and mother of two teenagers. She lives in Sherman Oaks.

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