I never really imagined I’d meet my boyfriend of four years in a random, mom-and-pop antique shop in Brooklyn. But I also never thought that — in the age of Tinder, Twitter, and Instagram DMs — we’d begin a two-month-long courtship strictly over email.
I stumbled upon the shop on an August afternoon, shortly after moving to the area. It was full of handmade gifts, vintage lamps, and other trinkets, with a small restaurant in the back — certainly not a place I’d go looking for someone to date. But while browsing, I came across a lamp I was interested in, and I looked up to see a tall guy with curly hair looking at it, too.
He introduced himself as Jason and seemed a bit shy — which, as an introvert, I could totally relate to. But after making some small talk, he ended up asking for my phone number. I was hesitant, as I often am (even if I think I like a guy), and stammered something along the lines of, “Could we stay in touch online?” assuming we would exchange Instagram handles as a way to get to know each other better. He said that he didn’t have social media but that we could stay in touch via email. I was admittedly thrown by the suggestion but also intrigued by his lack of social media. We exchanged email addresses, and that was that — it was practically a setup from a '90s rom-com.
I wasn’t expecting to hear from him, but the next day, I received an email saying how nice it was to meet me and asking me a bit more about myself. In return, he also told me about his background: where he was originally from (Rochester, NY), his age (8 years older), and what he did (finance). We chatted back and forth a bit over the course of the week.
Over email, I felt like I had the space and time to think about what I wanted to say and what I wanted to know — it didn’t feel as rushed or as ambiguous as texts or dating-app messages. It was old-fashioned, in a way — almost like writing letters to a pen pal or lover.
It was old-fashioned, in a way — almost like writing letters to a pen pal or lover.
After the first few days of getting to know each other via email, Jason asked me out. I politely declined and told him I just wanted to be friends, since I did really enjoy talking to him. I was pretty honest about the fact that our age difference — I was 22, he was 30 — made me feel unsure as well. But instead of giving up entirely, he was completely understanding, and we continued to email long letters to each other. The letters were mostly friendly but with some light flirting on both our ends.
For two months, we continued emailing, growing remarkably close for two people who had only briefly met, once, in real life. We talked about everything from the best cupcakes in our neighborhood and our favorite artists to places we hoped to travel one day. We learned a lot about what we had in common, too, and even helped each other discover new parts of our neighborhood, like restaurants and parks.
Meanwhile, I was still on dating apps and meeting suitors in real life — without much success. One bad date in particular really made me think hard about whether I should ask Jason out. He’d been a kind, active listener; a great friend; and an amazing support system. While the age gap had initially made me hesitant about pursuing him romantically, I had grown so comfortable talking to him, I felt like we’d known each other forever. Why not take the plunge?
I was insanely nervous as I hit “send,” shooting off the shortest email I had ever sent him: “Would you perhaps want to get brunch at the spot where we first met?”
His reply came almost immediately, and it was decided that we’d meet the next week. When our brunch date finally came, I saw the same slightly shy, smiling face right where I’d last left it. Talking to each other felt natural and fun, not stilted and awkward, like so many app dates had. We even ordered the same thing: pumpkin pancakes. After brunch, I wanted to hang out longer, so I made up an excuse that I had to go to an Italian shop a few blocks away to buy cheese and asked him to join. Even to this day, he jokingly tells me that’s the moment he fell in love with me.
Our long emails let us express ourselves and be honest in ways we wouldn’t have been able to otherwise.
While our courtship was unconventional in the age of dating apps, I’d argue that our long emails let us express ourselves and be honest in ways we wouldn’t have been able to otherwise, had I just taken his number that day in the store and started texting and dating him in the same week.
Maybe it's because I'm a writer, but I really loved getting to see his world and who he was through his words. In fact, it’s kind of beautiful to have a sort of archive of modern-day love letters that go beyond a text message. Even after four years, we still write each other long emails when we feel like it. Just for old times’ sake.