Dear Gillian,

There is a boy — a very cute, smart and well-dressed boy in my class. While 
I would normally go for it considering these attributes, hes also got that
, “Im top-tier and super-intimidating” swagger. How do I approach this? Staring 
lustfully across the room is not going so well. We have had absolutely no
 contact and he hasn’t expressed any interest, but there just seems to be 
something there (am I crazy?).

 – Drooling From Across The Room


Dear Drooling,

Crazy? You mean just because you believe in a romance between you and someone who doesn’t know you exist? Yes, you might be crazy, but not in a bad way. Let’s start with some lyrics. Here are the opening lines from Alicia Keyes’ “You Don’t Know My Name,” which does mention “crazy:” (The music video is everything you’d hope for from a early 2000’s production.)

From the day I saw you

Really, really wanted to catch your eye

Somethin’ special ’bout you

I must really like you

Cause not a lot of guys are worth my time


Oh baby, baby, baby

It’s gettin’ kind of crazy

Cause you are taking over my mind

And it feels like ooh

You don’t know my name

And here’s Antônio Carlos Jobim’s “The Girl from Ipanema,” a hit in the ’60s and one of the most covered songs in the 50 years since — there’s a great, soulful Amy Winehouse version:

Oh, but I watch her so sadly

How can I tell her I love her

Yes, I would give my heart gladly

But each day as she walks to the sea

She looks straight ahead, not at me

Tall and tan and young and lovely

The girl from Ipanema goes walking

And when she passes, I smile, but she

Doesn’t see. She just doesn’t see

But don’t feel too crazy, Drools, because you and your boy are precisely where every single love affair in the history of the world began — brimming with private passion and oozing with pure potential, but otherwise, nowhere. You are the secret admirer, like Shakespeare’s Viola in “Twelfth Night,” cloaked in a pretend disinterest. The question is how to de-cloak.

First of all, don’t let the top-tier swagger dissuade you. From Psyche’s betrothal to a supposed monster (actually Cupid in disguise, but not the point … ) to Ron and Hermione’s romance that overcomes her towering superiority in potions class and everywhere else, love often deals in non-superficial traits — charm, sincerity, perseverance and humor are surely among them, but they are innumerable. Your challenge will be to summon your strengths, your most attractive qualities, and get them into his view. How do you approach this, you ask?

You don’t have to be the Daily’s liberal arts advice columnist to know that you and Swaggy, although you’ve never spoken, have something obvious in common: the class! I’ll get to the point of this in a moment, but first, a couple of words of caution.

Drools, this might not work, so give it your all, but don’t get obsessed. Don’t cling like Velcro to a couple of passing smiles like the protagonist Professor Gustav von Aschenbach in Thomas Mann’s “Death in Venice.” He becomes erotically obsessed with a beautiful young boy, and stays in Venice stalking the lad despite the Cholera epidemic, of which he becomes a statistic. In the critically acclaimed 1975 Francois Truffaut film “The Story of Adele H.,” Victor Hugo’s daughter becomes irrationally obsessed with a military officer and does some world-class trans-continental stalking, certain they will marry. Of course, he thinks she’s a lunatic and she ends up spending 40 years in an asylum. Point is, erotomaniacal obsession is never a good look and always end badly.

As I said, you’re in a good place across the room. We often imagine love at first sight in more grandiose settings, like walking along the Seine, riding a wave in Waikiki, or on the steps of a grand museum. This sometimes happens. Often, however, it’s those we see everyday in our apartment buildings, regulars at our favorite coffee shops, or like you: in class.

“L’Amour de Swann,” one section of a larger work by Marcel Proust, details the beauty of quotidian, everyday love. Charles Swann begins to love the mundane things about his lover Odette and takes pleasure in her everyday rituals and actions rather than the idealized beauty and glamour he used to be attracted to. I wouldn’t take this relationship as a model, for it proves to be a painful projected illusion, but Proust brilliantly explores the ways in which a person can permeate our own day-to-day experiences.

So, as long as you remain grounded and don’t begin to creep around this guy’s life, you’ll be good. I’d advise you to build an approach around the class itself: suggest a pre-finals study session or a term paper critique swap, or even just ask for a day’s notes you may have missed. Find a class-centered way to start talking to this boy, preferably in a cozy coffee shop over some lavender-honey lattés, and take it from there. Crazier things have happened.

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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