Sophie Blackall’s illustration for a Missed Connection planning a meetup in Grand Central on Valentine’s Day. (Sophie Blackall)

In a city of more than eight million people and a subway system packed with 5.5 million riders daily, New Yorkers are primed for missed connections: sharing glances across a train — or even a conversation — with a person never to be seen again.

In steps Craigslist’s Missed Connections classifieds, a perfect medium to try to find that gone-but-not-forgotten commuter.

The ads, addressed to “cashier at the Thrifty deli on Broadway” (“I have bought soda from you like six times and I don’t even drink soda,” confesses a 20-year-old redhead pining over her Morningside Heights soda vendor) or “Spanish girl working at Heartland Brewery” (“I think you’re really cute and we smiled at each other,” writes “the asian guy” to his hostess crush), are often sweet or funny snapshots of momentary sparks flying between the denizens of a bustling city.

“It’s very romantic,” says Megan Gilbert, the target of a missed connection listing in 2007. “It speaks to New York and how every encounter is so fleeting with all these people everywhere; it’s very New York.”

The Transit Museum will be hosting its annual Missed Connections themed Valentine’s Day event on Thursday in Grand Central, featuring illustrator Sophie Blackall and writer Alan Feuer as speakers. Feuer writes poems based on Missed Connections ads; Blackall has a book of illustrations of Missed Connections ads titled “Missed Connections: Love, Lost and Found.”

Blackall recently posted a new illustration on her blog, for an ad describing an encounter in Grand Central. The man in the ad proposes a “ridiculously romantic plan.”

“Meet me under the stars on Valentine’s Day,” he writes to the woman he saw staring up at the star-covered ceiling with a book in her hand last Friday. “8pm. Bring your book.”

Blackall echoed the writer in her blogpost, with her own “ridiculously romantic plan.”

“Let’s crash this Missed Connection,” Blackall wrote. “I’m quite serious about this.”

Q & A with Sophie Blackall

DT: What prompted you to start illustrating Missed Connections?

SB: In early 2009 I exchanged smiles with a handsome fellow on a crowded subway train. When he got off at his stop, he shouted “missed connections” through the closing doors. It was the first time I’d heard the phrase. I went home and Googled and was instantly engrossed, reading message after message. Each one was a fragment of a story, a tentative love letter to a stranger, a hopeful, hopeless message in a bottle. I knew straight away I wanted to draw them, to illustrate these moments frozen in time. A selection of my favorites are collected in my book.

DT: Has anyone ever told you about realizing a missed connection you illustrated was about them?

SB: Yes, a bunch of people have come forward, sometimes more than one for the same message!

DT: Has anyone ever posted a missed connection about you, or have you ever posted one?

SB: Someone once posted a very meta message: “To the artist who draws Missed Connections, I think I love you. Maybe you’ll draw this message for your book!”

Connections missed and made

Lauren Shockey, writer of Four Kitchens

I posted a Missed Connections for a guy I saw at the Met: My post was something like “so-and-so at the opera, you were really cute, too bad you had a girlfriend.” The guy responded saying the girl wasn’t his girlfriend, which was a little weird, because they had their arms around each other. So I wrote back, “Even though you and your non-girlfriend seemed kind of coupley at the opera, if she is not in fact your girlfriend, we should hang out sometime.” We met for coffee at Starbucks but nothing ever came of it.

Michael Kaufman, freelance producer

I was on Elimidate and this girl from California posted a Missed Connection about me. She told me she and her friends would watch my episodes on repeat. It was weird; she would actually quote things I said on the show. We emailed for a little bit but she lived in California so that was pretty much it.

Megan Gilbert, writer

I was reading Philip Larkin on the G train. This attractive guy sat down across from me and every time I looked up he was looking at me — not creepily, in a cute way. I remember thinking to myself as I was getting off the train, “I’m single, I should look at that guy again.” I looked back and he looked at me out the window and smiled and I smiled and ran up the stairs all excited.

I was in grad school at the time and I used to poke around on Missed Connections for fun when I needed a break from reading, and I just thought, maybe he’ll post a Missed Connection — of course this is nothing I said to any human being because it’s ridiculous, I just thought it.

And he did! He actually quoted Philip Larkin, and I remember thinking, I can’t believe this is happening, especially because it’s really sweet and totally dreamy to quote Philip Larkin.

We had this back-and-forth over e-mail for a bit and then decided to meet up for a drink. So we’re having drinks and having a good time and then he’s like, oh yeah, I’m moving to Seattle tomorrow.

I kind of just like deflated, like what’s the point, I’m not going to go home with this person and I’m not going to start some long-distance thing. I think I said, “If you come back to New York I guess give me a call.” I guess I was looking for a relationship more than just some random person.

Mark Glassman, producer at Bloomberg, & Elaine Moran, senior correspondent for Fuse News
*as told by Mark

We met on the 1 train on Halloween in 2008, we were both in costumes. This is really embarrassing — I was dressed as a male Playboy bunny. You know, you go out dressed like that and it ends up being a story about how you met your wife so you have to tell the story for the rest of your life.

We had such a great conversation and I would’ve felt overly forward being this shirtless guy asking this girl for her number. I didn’t want to spoil the moment but I immediately regretted it, and the next day I put up a Missed Connections ad.

Elaine actually didn’t know about Missed Connections; she was lamenting to her friends afterward that she met a guy on the train and he didn’t ask for her number, and her friends told her to post something on Missed Connections. So the next day, she went to the site to post one only to find that I had posted one 12 minutes earlier.

We went out a week later and and basically picked up right where we left off. We moved in together about five months later.

I proposed to her on the 1 train on our three-year anniversary. We were transferring to the 1 at Times Square and I remember she was telling me a story about a friend of hers but I couldn’t remember a thing she said, I was so nerve-wracked about making the transfer. We got on the train and I said something about how I still regret not having asked for her number that time so could I give her a call sometime, and then I gave her the ring. If you ever want to surprise a lot of tourists, I recommend proposing to someone on a train.

Valentine’s Day at the Transit Museum

Thursday, February 14, 6-8 p.m.
Vanderbilt Hall, Grand Central Terminal
Tickets: advance $10/$7for museum members; at the door $15
* Head out to the main concourse afterward with Sophie Blackall to crash a missed connection meeting at 8 p.m.!

Follow Danielle Tcholakian on Twitter @danielleiat