How to get a guy to flirt with you? I messaged him on LinkedIn

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 grumpy about change. It’s not that I don’t like the people I work with. I really do. It’s just that, especially at rush hour, I’m not a fan of the 101 and 405 or the alternate canyon routes. Plus, I have an elevator phobia, and our West LA office is on the ninth floor. (Props to the kind and wonderful security guard who comes with me most mornings.) But the good stuff comes to those who return to the office, besides the camaraderie and free snacks. We’ll call them J.

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

Then one day I saw J waiting for a lift. I was just passing through. But I liked what I saw: a strong jawline, a bit of scruff, broad shoulders and the unmistakable curve of biceps under the shirt. J was older than the younger guys. There was something else. Out of the corner of my eye, I realized he was also following me as I left. I understand that not every woman gets this kind of attention. But a few years after the divorce, I’m capitally single. I liked the feeling, at least in this case.

I’ve seen J in passing a few times. He seemed friendly, but I’m not the best at picking up or putting off those kinds of vibes: the “I’d like to get to know you better” ones. I’m not sure what the straight gaydar equivalent is – “straightdar” just doesn’t have the same ring – but I’m pretty sure I don’t.

Then one day as I was walking back to the office with my elderly dog, Loki, who comes to work with me, I bumped into J. I can’t remember exactly what he said. But he was super sweet with my chicken. He knelt down to stroke him. A guy who is nice, engaged and nice to my dog? I’m not saying this is necessarily the holy triumvirate. But it’s pretty good. Who was this guy? I wanted to know his name. Since most of the offices in our building, including J’s, have a sign outside with the company name, this didn’t require any complex detective work. I immediately found him on LinkedIn. I was happy to have a name. I had no more plans.

A day or two later, late at night, after my usual bedtime, and apparently past the clock of my inhibitions, feeling that I had nothing to lose but my pride, I decided to do something unusual: See if I could get a message to J. I went back to LinkedIn and found that I can send him exactly one message, even though we have no connections in common. (Without a response from the recipient, LinkedIn informed me, my message would essentially be DOA.)

My subject: Bold question. My message: “Hi. I work on the same floor as you. I’m the woman with the crazy curly hair. Want to go for a walk or grab a coffee or a drink sometime? I’m not in the habit of doing this, but you’re cute and you look cute. If you’re not alone, I hope you’ll take the compliments and ignore the rest. Leslie”

I hit send and immediately had two distinct reactions. One was the equivalent of “Go 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 aloud to his group of 20-something colleagues. They would all know exactly who they are, every single one of them. It wasn’t exactly a Hester Prynne situation. Still.

A day passed with no response and I came up with a new scenario to worry about – a specialty of mine. How would I know if he received my message? The lack of a response meant one of two things: he hadn’t received the message at all, or he had and chose to ignore it. I wanted some assurance against the first possibility. But even if I could find a way to still text him—or horror of horrors—I’d be forced to ask him in person if he got my message, and he did, but he didn’t care, then I’d seem and worse.

But that’s not what happened. Instead, the next morning, I received a short, flirty, but entirely appropriate message from J on LinkedIn.

From there, we started texting. “Good morning Leslee. This is J from the 9th floor. How are you this AM?” it started. A few days later, we met at Teaspoon, one of the many boba places on Sawtelle Boulevard.

Towards the end of their time together, he put his elbow on the table and raised his open palm. I thought he might challenge me to a fight. Did he know that I used to beat all the boys in elementary school? He asked me to put my palm on his. He made sure I was okay with it. I didn’t hesitate. It felt good.

Because we both prefer to keep our work and personal lives separate, neither of us necessarily want our coworkers to know about it, whatever it is, which made for some funny and funny moments. There is a mutual understanding between me and J that this is not a happily ever after story, but it was a lot of fun. I’m glad I decided to go for it – in my own reserved way. As J wrote to me 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.

LA business chronicles the search for romantic love in all its glorious guises in the LA area, and we want to hear your true story. We pay $400 for a published essay. E-mail [email protected]. You can find submission instructions Here. You can find previous columns Here.