Dear Gillian,

This past Friday I went to a bar with some friends. When we finally escaped the line outside and entered this underground space, I immediately headed to the bar for a drink. It was there that I saw him. Brown silky hair and green eyes. I was instantly mesmerized by this complete stranger. I spent the entire night trying to come up with a line or something to say to him, but at the end of the night I went home without even speaking to this man. This is why I am writing to you. I have never been good at approaching people at bars. The idea of rejection terrifies me; maybe he already has a partner, maybe he has no intention of speaking to strangers at a public bar or maybe he too wanted to speak to me, but was just as nervous. As I headed home, I thought that if I was perhaps in a class with this man or if he was attending a house party that I was at, I would have approached him. Something about being at a bar and talking to stranger has always intimidated me. How can I overcome this fear of rejection?

 – Lust at First Sight

Dear Lust,

From the tabernae along the Appian Way to Beowulf’s Mead Hall to the Mos Eisley Cantina of Star Wars, bars have always served as places of edgy, vaguely dangerous adventure. Whether they lead to anything or not, there’s an excitement to encounters with the unintroduced. Though not everyone you approach will be available or interested, neither will anyone judge you for testing the waters and sussing out your stranger.

Unlike your counterexamples from class or a house party, encounters at a bar are based on having very little in common besides what’s assumed by venue choice. The crowd at Aut Bar is way different from that at Skeeps, and both are different from that at Rush Street. Then again, we’ve been to them all; the smaller the city, the less niche-y its spots can afford to be. At a house party, you have the hosts in common, or at least run into the same groups of friends; in class, you share an intellectual interest or at least a desire to pass. Bar patrons can be anyone from anywhere, and connections tend toward the lowest common denominator. (The fact that those might be too low for your instincts, Lust, is not a bad thing.) For these reasons, bars as pick-up spots tend to conjure images of uncertainty, romantic emptiness or even sleaze.

So why do you keep regarding bars as places of romantic potential? Jay McInerney sums up the paradox in his novel “Bright Lights, Big City”: “The problem is, for some reason you think you are going to meet the kind of girl who is not the kind of girl who would be at a place like this at this time of the morning.”  

Depending on the vibe of your spot, though, it may be a really nice place for some flirtatious chat. Then comes your next problem: a dearth of information. Is he interested in your gender? Is he interested in you? Is he single? Does he remember last week when you made eye contact at the other end of the bar? Look at Archibald Motley Jr.’s painting “Nightlife.” Documenting the Black social life of Bronzeville, Chicago’s South Side community, the background of the painting is injected with the exuberance and rhythm of the jazz age. In the foreground Motley captures the disjointed and thorny drama of the scene: a man at the bar can summon only enough courage to get his upper body to beckon, his hips and feet still unmoved facing the bar. This hesitancy results in an ambiguous gesture that leaves the three women confused about who he wants — one who’s taken, one who wants him and one who hasn’t even noticed.

Now, Lust, in case you want some, the liberal arts offer some clever pick-up lines and here are several examples:

Sylvia Plath: “Kiss me and you’ll see how important I am.”

Patti Smith: “Will you pretend you’re my boyfriend?”

Pablo Neruda: “I’d like to do with you what Spring does with the cherry tree.”

Gary Shteyngart: “I’m the fortieth ugliest man in this bar. But so what! … Isn’t this how people used to fall in love?

F. Scott Fitzgerald: “I like large parties. They’re so intimate. At small parties, there’s no privacy.”

That reminds me: I’ve been meaning to warn you against adopting Gatsby’s game. Don’t rent out The Last Word, publicize it robustly and arrange the invite of your green-eyed hottie. Things go terribly wrong if you try to deploy contrivance after contrivance to draw your Daisy close. So even if you’ve taken a trip to the bathroom for a quick Facebook stalk after catching a glimpse of his signature as he closed out his tab, resist the urge to name-drop that mutual friend of yours or ask how he enjoyed last semester in Copenhagen.

You write of the moment when you were instantly mesmerized, Lust. There’s nothing that takes you out of the mundane like the non-verbal communication of a stranger’s gaze. For Baudelaire, this was at the heart of the experience of the modern city. You might give a read to his poem, “To a Passerby,” a meditation on the anonymous figure who walks into your life and right on by. While it’s great fodder for poetry, I’d suggest avoiding the fixation of a voyeuristic flâneur; it’ll be creepy. Let that moment stir you, but stop staring.

I’m assuming you’re not at this bar alone. Friends (his, yours) can help reduce the fear of rejection. It’s best, though, to avoid any overt competition or goofiness like the sailors on shore leave in Jerome Robbins’s ballet “Fancy Free.” The sailors don’t know what to do with their sea legs in the big city filled with beautiful broads. They fumble over each other (with exquisite choreography) for the poor gals’ attention.

If after all this you still want to get better at approaching guys in bars, you might watch Diane Keaton in the 1977 film “Looking For Mr. Goodbar,” based on the Judith Rossner novel of the same name. Her character seems to have no problem night after night. But it ends horribly.

I don’t know if this is the advice you want, Lust, but I believe your intimidation about approaching strangers at bars is healthy and noble. No matter how fine these strangers may be, hitting on them in that milieu is not naturally your thing, and there’s nothing wrong with that. I’d keep my ears alert and listen for an invitation to join the conversation, head to the dance floor or make come-hither eye contact. If nothing of the sort presents itself, all is not lost. When you get out of the bar, you can drop your intimidation like a bad Econ course and not rest until you find a way to meet this young man in a context that suits your style.

Send an email to or anonymously here describing a quandary about love, relationships, existence or their opposites. Gillian will attempt to summon the wisdom of the arts (literary, visual, performing) to soothe your troubled soul. We may publish your letter in the biweekly column with your first name (or penname). Submissions should be 250 words or fewer and may be edited prior to publication.

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