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Love Stories From Hopeless Romantics

Craigslist's Missed Connections section is essentially a type of personal advertisement which is posted after two people meet but are too shy or otherwise unable to exchange contact details.

The Missed Connections section on Craigslist receives thousands of ads every month for major cities across the United States. In New York City alone, there are 8,000 postings per week. Each region has a common arena for their "missed connection" – in the Pacific NW, the most common location was on the bus; in the Pacific SW, it was the gym; in the North East, it was the subway and train; in the Midwest, it was the supermarket; in Texas and the Gulf, it was Walmart (I sure hope this isn't an indicator of where singles are searching for love in Texas).

Some ads are short and mindless, while others resemble heartfelt messages in a bottle. Some are searching for a person with whom they only shared a moment, while others call out men with secret families who had changed their phone numbers. Then there's the post of a man catching a glimpse of his ex-wife on the L train. In the post, featured in This 'Missed Connection' Is Heartbreaking In The Best Possible Way, the man recalls how he married a woman back in the 1980s to win a bet placed by a college buddy. "Half-drunk, and half-in love" when they said "I do," the pair rushed to have the marriage annulled three days later. Distance and time had separated them until recently, when the man says he spotted his "ex-wife" on the L train in New York City.

In these short romantic bursts, people strive for a connection. All human beings ache to be less alone, to be connected to others. And, what a serendipitous way to meet the love of your life, which is all so rare these days. However, people choke when it comes time to actually utter a sentence or a simple "Hi" to their crush.

"Should I pretend I'm lost and ask her for directions? No, I don't want to look like a dumbass."

"Should I comment on the weather? No, we're below ground numb nuts!"

"Should I compliment her? No, that would be way too direct."


Of course, he always finds reasons as to why he shouldn't let actual words leave his mouth and by the time his inner battle ends, she's gone. He has let the inner voice win and he's left to sulk in his own defeat. A perfect example and one of my favorite and most poetic of Craigslist missives (albeit a bit dramatic), reads like so:
“I saw you on the Manhattan-bound Brooklyn Q train.

I was wearing a blue-striped t-shirt and a pair of maroon pants. You were wearing a vintage red skirt and a smart white blouse. We both wore glasses. I guess we still do.

You got on at DeKalb and sat across from me and we made eye contact, briefly. I fell in love with you a little bit, in that stupid way where you completely make up a fictional version of the person you’re looking at and fall in love with that person. But still I think there was something there.

Several times we looked at each other and then looked away. I tried to think of something to say to you — maybe pretend I didn’t know where I was going and ask you for directions or say something nice about your boot-shaped earrings, or just say, “Hot day.” It all seemed so stupid.

At one point, I caught you staring at me and you immediately averted your eyes. You pulled a book out of your bag and started reading it — a biography of Lyndon Johnson — but I noticed you never once turned a page.

My stop was Union Square, but at Union Square I decided to stay on, rationalizing that I could just as easily transfer to the 7 at 42nd Street, but then I didn’t get off at 42nd Street either. You must have missed your stop as well, because when we got all the way to the end of the line at Ditmars, we both just sat there in the car, waiting.

I cocked my head at you inquisitively. You shrugged and held up your book as if that was the reason.

Still I said nothing.

We took the train all the way back down — down through Astoria, across the East River, weaving through midtown, from Times Square to Herald Square to Union Square, under SoHo and Chinatown, up across the bridge back into Brooklyn, past Barclays and Prospect Park, past Flatbush and Midwood and Sheepshead Bay, all the way to Coney Island. And when we got to Coney Island, I knew I had to say something.

Still I said nothing.

And so we went back up.

Up and down the Q line, over and over. We caught the rush hour crowds and then saw them thin out again. We watched the sun set over Manhattan as we crossed the East River. I gave myself deadlines: I’ll talk to her before Newkirk; I’ll talk to her before Canal. Still I remained silent.

For months we sat on the train saying nothing to each other. We survived on bags of skittles sold to us by kids raising money for their basketball teams. We must have heard a million mariachi bands, had our faces nearly kicked in by a hundred thousand break dancers. I gave money to the beggars until I ran out of singles. When the train went above ground I’d get text messages and voicemails (“Where are you? What happened? Are you okay?”) until my phone ran out of battery.

I’ll talk to her before daybreak; I’ll talk to her before Tuesday. The longer I waited, the harder it got. What could I possibly say to you now, now that we’ve passed this same station for the hundredth time? Maybe if I could go back to the first time the Q switched over to the local R line for the weekend, I could have said, “Well, this is inconvenient,” but I couldn’t very well say it now, could I? I would kick myself for days after every time you sneezed — why hadn’t I said “Bless You”? That tiny gesture could have been enough to pivot us into a conversation, but here in stupid silence still we sat.

There were nights when we were the only two souls in the car, perhaps even on the whole train, and even then I felt self-conscious about bothering you. She’s reading her book, I thought, she doesn’t want to talk to me. Still, there were moments when I felt a connection. Someone would shout something crazy about Jesus and we’d immediately look at each other to register our reactions. A couple of teenagers would exit, holding hands, and we’d both think: Young Love.

For sixty years, we sat in that car, just barely pretending not to notice each other. I got to know you so well, if only peripherally. I memorized the folds of your body, the contours of your face, the patterns of your breath. I saw you cry once after you’d glanced at a neighbor’s newspaper. I wondered if you were crying about something specific, or just the general passage of time, so unnoticeable until suddenly noticeable. I wanted to comfort you, wrap my arms around you, assure you I knew everything would be fine, but it felt too familiar; I stayed glued to my seat.

One day, in the middle of the afternoon, you stood up as the train pulled into Queensboro Plaza. It was difficult for you, this simple task of standing up, you hadn’t done it in sixty years. Holding onto the rails, you managed to get yourself to the door. You hesitated briefly there, perhaps waiting for me to say something, giving me one last chance to stop you, but rather than spit out a lifetime of suppressed almost-conversations I said nothing, and I watched you slip out between the closing sliding doors.

It took me a few more stops before I realized you were really gone. I kept waiting for you to reenter the subway car, sit down next to me, rest your head on my shoulder. Nothing would be said. Nothing would need to be said.

When the train returned to Queensboro Plaza, I craned my neck as we entered the station. Perhaps you were there, on the platform, still waiting. Perhaps I would see you, smiling and bright, your long gray hair waving in the wind from the oncoming train.

But no, you were gone. And I realized most likely I would never see you again. And I thought about how amazing it is that you can know somebody for sixty years and yet still not really know that person at all.

I stayed on the train until it got to Union Square, at which point I got off and transferred to the L.”
Okay, well, most people wouldn't excessively preoccupy their minds with a stranger riding the subway for sixty years, but you get the point (and what a beautifully written post!)

People become poetic, hopeless romantics, so consumed with an urge to make that connection, yet frozen with hesitation and fear. If only they had said something in their initial impulse. If only there wasn't a lingering cloud of self-imposed pressure to make the perfect first impression. Because in reality, wouldn't you rather fall and spill your coffee all over your beloved, if it wins yourself a conversation, then silently wait in the corner of the L train, waiting for a moment when you can compliment him on his loafers? Because, that time may never come and before you know it, he and his loafers are getting off at the Quincy brown stop.

If you're really on top of your game, just follow Megan Baldwin's lead. In her article, Missed Connections: Dating Advice I've Learned From Craigslist, she urges women to ride the subway in pursuit of finding her dream man (or just steal someone else's Missed Connections ad). Or, you can take her bold approach of crafting love business cards. "I've recently had the folks at Staples create a 'love' business card with the most important facts about me -- for example: I enjoy bowls of cereal and am directionally challenged. Or you could just have one made with your name and phone number and maybe a headshot if you're photogenic. In this way, I will never let someone great or even just great looking walk on by," she admits.

While success stories were not abundant in my research, I did stumble upon this encouraging Missed Connections story from SwirlSpice:

"The story of how Alyssa Good and Matt MacDowell met seems straight out of a Hollywood romantic comedy. She’d taken a seasonal job at a department store at the Mall of America and he came into her section. They chatted amiably; then he left, with Alyssa charmed but certain that someone so sweet was already spoken for. Days later, a friend of Alyssa’s directed her to a Craigslist Missed Connections ad that seemed to describe her perfectly. Alyssa responded, and she and Matt emailed for a couple of weeks before finally meeting for coffee on a cold January night. They talked for three hours, closing down the coffee shop, and haven’t been apart since. Their wedding was filled with personal touches, from Alyssa’s graphic design on the printed materials to the handmade seating chart they made out of corks collected from friends and family members."

Life is strung together by small moments – it's what you do with those moments that count.

Taylor Wade

Taylor is one of the founders of Ambiance Matchmaking. She now dedicates her time to curating content for our community through her podcast and blog. Writing and podcasting is the art of great story-telling. As a relationship writer and editor, she has always sought to capture the reality of the dating experience, full of drama, friction, and joy. The best mind is an open mind, so she specializes in asking questions and approaching a story without preconceptions.

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