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Jack: The Beginning

Jack: The Beginning

How we met and how I knew

Lee Tilghman's avatar
Lee Tilghman
Jul 14, 2025
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Jack: The Beginning
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About a month ago, when I was feeling a mixture of anxiety, frustration, and writer’s block, Jack knew exactly why. I’d been keeping us private, which was my decision, one that he supported wholly.

I wanted to keep the early stages of our love to ourselves. It was too real to share with the internet, and I wanted to be 100% with Jack, not performing a love for content. I learned my lesson during my influencing days, when I shared a relationship before I was truly sure of it, because I felt like I had to, and honestly, because I thought it would “do numbers.” As I write about in my memoir (pre-order now, gotta plug that), that choice taught me a lot about what I want to protect, and what’s worth keeping just for me.

But it was becoming increasingly hard to keep such a huge thing out of my life. I jokingly told a friend years ago I wouldn’t share about my love life until I had a ring on my finger. That time has come.

Jack supports everything I do. He understood why I wasn’t sharing, but he also gently reminded me that I’m a writer; I write and share about my life for a living. And Jack is a huge part of that. I started writing this essay a month ago, and I knew I’d share it when I was ready. Now, I’m finally ready. So here I am, writing about Jack: how we met, our love story, and everything in between.

Our first two dates were giggly.

From the very first moment I saw Jack’s face at Long Island Bar, I felt at home. I clocked his smile peeking above the sea of people as soon as I walked in. Jack has the world’s best grin; it was the first thing I noticed about him.

I was immediately at ease as I stood in front of him and we hugged hello. We’d matched on Hinge—I’d “hearted” him, but he’d asked me out. I’d given him short replies (I’d known better than to invest too much effort on Hinge, especially in the messaging phase): “can’t that night,” “maybe”—until we finally landed on a date. It was a freezing February night, a week from my 35th birthday, the kind where the wind whips in your face and you ask yourself, Why the FUCK am I doing this?

Oh yeah, your brain answers, to find the love of my life.

Jack and I talked so long that I realized we’d been standing at the bar for 30 minutes without drinks. Teasing him, I said, “So…are you going to get us drinks?”

Moments after the proposal

Later, we would laugh about this. He told me it was because we were on a roll, and he didn’t want the moment to end. And on a roll we were, chatting with each other felt so natural, the words rolling off the tongue.

When Jack (finally) left my side to order us drinks, a girl slipped from the bar and came up next to me, said she was a fan, and wished me luck on the rest of our date. I smiled and said thanks. I thought it was fitting; a private moment mixing with a public one, like God gently reminding me that my life has always unfolded a little bit in front of others. If you’re that girl from Australia and reading this now, I think this story will make you smile.

The rest of the date was spent smiling and laughing, talking and getting to know each other. It was casual; we both had dinner plans with our friends right after, so it didn’t last long. I was relaxed and pumped up. I could have hung out with him for hours. Smiles lingered. His big blue eyes pierced mine. Jack has an essence of openness, steadiness, and sweetness that made me feel safe. We hugged goodbye. I knew I wanted to see him again.

After our date, I went to dinner with my friend Cate. “So how was the date?” she asked. “It was so good,” I said.

“Why are you here with me? If you had fun, you need to let him know. Are you gonna text him?”

“I don’t know yet!” I responded.

She urged me to be myself and not play games. Up until I met Jack, I’d been trying to play the “black cat”, not initiate and let the guy do the chasing, but when I realized that sometimes even that approach didn’t guarantee a relationship, I was ready to throw all the stupid TikTok dating rules out the window.

I let her advice wash over me, and on the way home, I texted Jack, “I had fun! Did you? Do you want to hang out again soon?” Jack said he did, and we continued texting. Feeling confident the next day, I asked him out for drinks that night before I was to meet up with my friend Estelle, who was in town from Paris.

It was snowing as I walked to our second date. We made plans to meet at a cocktail bar in Cobble Hill, but it was closed for an engagement party. As we got turned away from the door, I remember having a funny feeling about that… like how ironic it was that this bar was closed for something we might do down the line.

Together we walked to a different bar in Boerum Hill called Grand Army and shot the shit, though we both don’t drink. We kept talking, and this time we did it for hours. We talked about our careers, our love of travel, and our goals for the future. I remember some moments of quiet as well. Jack was comfortable in his skin, and I took deep breaths and let that comfort wash over me, too.

It was nearly 11 when Jack closed the bill. We headed outside into the snow, and he went in for a kiss right out front of Grand Army.

It was the most perfect, sexiest makeout sesh I’d ever had in my life. And it was quintessentially New York, too, because as the snow fell around us and dusted our eyelashes, a homeless man approached us. “Excuse me. Can you buy me dinner?”

Jack, clearly into the kiss, didn’t seem to notice. The homeless man repeated himself a few more times. I grabbed Jack’s hood around his face, pulling myself closer to him to protect us from the staring passerby and the homeless man who kept heckling us. Jack cleared us away from the sidewalk, where we continued to lock lips.

I went to Public Records afterwards to meet up with Estelle, and the whole night on the dance floor, I smiled to myself, thinking about Jack and our kiss.

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