The art of 'A Shot in the Dark': how Sophie Blackall was drawn to Missed Connections

Children’s book illustrator, Sophie Blackall, was on the subway when she noticed a man mouthing something to her through the train’s window: “Missed Connections.” This encounter did not lead to love, but it did expose Blackall to the realm of “Missed Connections” and “Shot in the Dark” forums where the hopeful post electronic messages in a bottle to people they met, and lost, in the pulsing tide of city life. While some messages were crude or boring, others captured her imagination by hinting at a world of tenderness just beneath seemingly trivial encounters. Blackall began illustrating one message a week and posting these on a blog. Before long she had a following and a book deal. On the eve of the release of Missed Connections: Love, Lost & Found, I had my own fleeting connection with Blackall in which she opened up about the artist and the inspiration behind her alluring illustrations.

Shawn Alff: Most of the characters you illustrate in Missed Connections have Mona-Lisa-style, half-smiles as opposed to toothy grins. Was this intentional?

Sophie Blackall: These moments are so subtle and passing… Even the person posting these messages really doesn’t know if the other person felt that same connection. For whatever these moments contain, it is so ephemeral and fleeting, and I think the half-smile is probably an indication of that.

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SA: Why do so many missed connections occur when either party is reading a book? Are readers just more introverted and shy, or are you drawn to posts written by people who have a better feel for the language?

SB: Oh, that is probably true. A ton of the missed connections are just basic, ‘You were incredibly hot at the gym,’ or ‘You pulled up in your whatever vehicle in Dunkin Donuts.’ I have to confess that those kinds of posts do not appeal to me visually. I really can’t draw cars and I don’t want to draw anything with a logo. But I try not just to illustrate ones that appeal to me personally. I did choose many messages that, if I would have been the recipient, I probably would not have responded to. I am also really shameful in judging people on their grammatical errors, which I am not proud of, but I did include plenty with sort of endearing language mistakes.

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SA: You seem to be drawn to posts that are almost seductive.

SB: I think so. Some of the posts sound as though the writer was completely drunk, which can be really funny. The posts are not great works of poetry or prose. They are messages dashed off, and I really like that uninhibited kind of spontaneous feeling. Some are written as poems and they do not appeal to me as much because they seem a little contrived and stiff. I do love the ones written with the kind of mentality that is like, ‘Well it’s four o’clock in the morning. I just got back. I’ll probably never get a response to this, but I may as well throw a message into the dark and see what happens.’

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SA: Ernest Hemingway’s shortest short story reads as a classified ad: “For sale: baby shoes, never worn.” He was also a proponent of the idea that a story should be like the tip of an iceberg, implying a larger layer beneath the surface. Is this part of what makes missed connections so compelling for you?

SB: Absolutely, in the same way that Hemingway's short story did, but also the way does. PostSecret began with a guy inviting people to anonymously write a secret on a postcard and drop it in the mail. He has had millions of them, along with a website and books. They are often just a few words, but they are chilling, heartbreaking, hilarious, and stunning because they are people’s honest secrets. They are the beginning of a story and that is absolutely what I love about missed connections.

Lots of people assume I must want to know if the couple gets together and if there is a happy ending. Part of me is not so interested in a happy ending because I just love all the possibilities in that fraction of a moment.

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SA: Do you think more people fantasize about individuals they have had only minimal contact with?

SB: Absolutely. With most instances of ‘love at first sight,’ you are given maybe a few visual cues and the rest you fill in. In that moment you don’t wonder if she has an overbearing mother or if he has halitosis. In that moment, that person is whatever you want him or her to be, and you can keep that going for ages.

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SA: From romance movies like Twilight or Message in a Bottle, it seems many women are attracted to shy men who are obsessive and given over to the notion of fate or love at first sight. However, in the real world when a man demonstrates these same traits, it is often seen as creepy or stalkerish. Is it just that women like to fantasize about a handsome man quietly pining for them as opposed to the reality of the smelly man staring at them on the subway?

SB: That is a tricky one. My boyfriend is always jokingly accusing me of liking a certain type of man. I have said to him time and again that this is actually the kind of man I like to draw. For me, I have this visual fantasy, a kind of aesthetic, for this sort of slight framed guy, possibly with a mustache. But this is not really who I want to fall into bed with at the end of the night. It is an aesthetic, not an attraction. But, I remember once in The Simpsons—I can’t believe I am referencing The Simpsons—but Lisa was reading something called, ‘Nonthreatening Boys for Girls.’ I think that is really true for teenage girls and many young women as well; the men they are attracted to are nonthreatening, this kind of effeminate, Johnny Depp, sensitive, gentle figure. Obviously this doesn't go for everyone. Some people must be drawn to footballers.

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SA: What are the differences between illustrating a children’s book and a book like Missed Connections?

SB: When illustrating for children, especially in America, you have to be very conscious about being politically correct. I once had a character smoking a cigar and that was considered inappropriate to have in a children’s book, for understandable reasons. There is a whole list of silent rules for children’s books. Because Missed Connections started purely as a personal, self-indulgent project, I did not have any rules. I wasn’t doing it for anyone but myself, so anything was fair game.

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SA: Do you think the publishing industry is moving toward a business model where an author’s work must be validated online before it is published?

SB: I think there is certainly evidence of that. I tell students all the time to start a blog. It is free. It is a framework for publishing your work so you can get it to an audience. You have complete control over it.

For me blogging was a form of discipline. I always have more than enough work, so to do a project I have to have a reason. I can’t just do it and stick it on the shelf. I knew this was a good idea. I knew I would never do it unless there was someone making me do it, even if that person was an imaginary virtual person I was never going to meet. And it worked for me. I just set myself a goal of doing one drawing a week and posting it. I didn’t tell anybody about it, not friends or family. The most amazing thing was how people just stumbled on it. It still amazes me that you can quietly put something online with no fanfare and people will actually find it. I didn’t even put a link from my website, but before long strangers started emailing me.

With publishers being in financial distress along with everyone else, I think they no longer have the ability to throw money at a project and not mind too much if it does not work. They have to be much more cautious. If they can see that something has a following, and a great amount of it is already done as opposed to just a sketch on the back of a napkin, I think that really appeals to them.

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SA: Do you think online daters could learn anything about writing an enticing profile from the missed connections you find appealing?

SB: I am always surprised, and I shouldn’t be, but I am, that people are really moved by any evidence of tenderness. That seems to be the thing that people really want to see, and which they kind of crave. Whenever I do a drawing that is really sweet, and warm, and tender, I get twenty times as many comments, emails, and responses than when I do one that is funny or a little naughty. The ones that make me laugh get responses, but not in the same way. While I was doing this for my own reasons, people were responding for their own reasons. They saw evidence that people are sensitive and tender and do notice tiny details in others. This was enough to give them hope. Maybe someone was seeing them in that way, and maybe someone will write about them tomorrow. They want to believe that this kind of connection can actually happen. Not everybody, but a lot of us are inclined to sort of be clever or funny, and I am certainly not wanting to steer people away from that, because clever and funny is good, but people do want that tenderness and honesty.

Check out more of Sophie Blackall's Missed Connection illustrations , like her on Facebook , or check out more of her work at

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