Dear Dr. Perfect,

There’s this girl at work that I have a total crush on. We get along super well and sometimes hang after work. I really like her, and I know for a fact that she’s single. I’m worried that I’ll ruin our friendship by asking her out, or worse, we break up and things get really weird.

I want to figure out how to ask her without putting pressure on her. But at the same time, I don’t know if I should ask her at all. Thoughts?

Sincerely,

Co-Worker

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Dear Hopeless Romantic,

You’ve come to the right place. I’m a bit of an expert on the language of love. Of course, I’ve toiled through the mysteries of romantic attraction as long as any philosopher or deadbeat poet. What I have learned is that courtship is weird.

The animal kingdom has methods not too far removed from our own. Birds awkwardly sing for their mates. Lizards puff out their chests. Lions fight one another for a chance with the lioness. The loser is roundly rejected and further humiliated by the lioness with a kick of sand to the face. I’m not sure what sand crabs do. I’m not even sure why I thought of sand crabs. I am hungry for seafood.

You have reached a pivotal moment where you don’t know if your coworker is interested. It’s hard to tell, as only creeps mistake casual friendliness for romantic interest. Don’t be a creep. Another unwritten rule of the dating game involves maintaining one’s dignity. If she knows you like her and her feelings aren’t mutual, you’ll be forever branded with the scarlet “L” (for loser).

But wouldn’t she be flattered? Not necessarily. Women can detect desperation like a hard-boiled PI. They’re experts on tone, body language, confidence, and fear. Just ask my mother.

I once sought her advice in asking a certain girl to the high school prom. She turned from the pot of boiling chili on the stove and mapped out varying scenarios with potential outcomes on a sketchpad. She was also an advice columnist for our hometown paper, The Grand Rapids Gazette.

“Whatever you do,” she advised, “don’t overanalyze things.”

“Isn’t that what we’re doing now?” I asked.

“Listen to your mother,” my father said from the corner of the kitchen, watching us.

“Where’d you come from?” I asked.

You’ve already completed step one, establishing her relationship status. The next step is to gauge her interest. Ask her to someplace casual (coffee shop, casino cruise, gun show, etc.). Send her some anonymous flowers and observe her reaction. 

If she’s receptive to any of this, give it a shot. If unrequited, never talk to her again.

If you are fortunate enough to garner her interest, take her to a movie. I don’t want to generalize, but all women love The Notebook (some men too). They go crazy for it. Breakfast at Tiffany’s is another one. Read some Henry James. He spent most of his literary career trying to figure women out. The works of Jane Austen also provide some helpful insight into the female mind.

Don’t give up until you have to. That’s what my mother used to say.

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Dr. Perfect has slung advice across the globe for the last two decades due to his dedication to the uplift of the human condition.