Dear Dana: How Can I Be A Better Flirt?

Dear Dana is a bi-weekly advice column for humans who engage in romantic relationships. Please send your dilemmas, issues, conundrums, assumptions, conflicts, anxieties, worriments, obstacles, complications, predicaments, queries, questions, and any other synonyms for “problems” to

Dear Dana:

I am an introvert. I am definitely not shy, but I suck at using my words.

When I like a guy, I never know what to say. I can only interact with him if I frame it as a friendly conversation, but as soon as I decide to think about it as flirting my brain stops working. Since I don’t want to come off as desperate or dumb, I end up over thinking everything and I come off as desperate AND dumb. I hate it. 

On luckier occasions, when I somehow manage to get myself a date or two (or ‘is it a date? Because there’re more people here than I was expecting?’) I dread the interaction. I don’t know how to flirt. I don’t know what to do or say when I am at the bus stop and the guy is there, waiting for me to give him a sign or something, and I give him nothing and he gives me nothing (i.e. kisses) in return.

How can I develop a style of flirting that feels natural to me? I bet I need more confidence, but my main issue is with WORDS. They leave me standing there, alone with the guy and they never show up, at least the good ones don’t. Help!



Dear Wordless:

When I was in high school, a guy friend challenged me to a staring contest during lunch. I agreed and peered directly into his brown eyes for so long that I lost track of time and I didn’t hear the bell ring and I still don’t know who won because I was too busy having the most erotic experience of my young life.

How was I so sheltered that a friendly staring contest became the hottest thing in my world? Because, at the age of 15, I had not made deliberate eye contact with a boy until that moment. I was terrified of the idea of flirting and avoided it at all costs. I figured that if I flirted with a boy he would know for sure that I liked him and instantly reject me or, even worse, ask me out and then I’d have to go out with him and we’d make out and I’d be bad at it and I’d get pregnant and he’d convince me to smoke PCP and we’d end up in a shoot-out, and I don’t know why I thought a first date would be like the movie Training Day plus groping, but I did.

I was afraid of flirting because I was afraid of what followed. I wasn’t ready for any sort of romantic entanglement so I put up walls to keep all suitors out. These walls come in handy when I’m riding public transportation, but they are not at all helpful when I want to indicate to a guy that I’m interested in him.

Fear of flirting is based in the fear of rejection. You’re afraid that if you allow yourself to speak freely, your thoughts and your feelings and your desire will come spilling out and the object of your affection will say, “Nope,” and you’ll be left there, open, wanting, and alone.

But, eventually, I learned how to flirt. At 10am on a Saturday morning in 2008 I sat in an auditorium at Second City Chicago, groggy, awkwardly balancing my coffee in my lap, and wondering why I was wasting my time attending this orientation for new students. I had just signed up for their introductory improv class because I was craving attention and creative fulfillment and to do something that made my heart race.

The head of the training center stood on the stage in front and spoke out into the audience, “This training is going to change your life. You probably don’t believe me, but it will.” I thought that she was very good at making people feel better about spending $300 a class.

But then I attended the classes. At first we were throwing fake balls around at each other and I thought I had absolutely wasted my money, but I stayed and went through the courses. I took improv classes for two years and they absolutely changed my life. They taught me how to open my mouth and, without knowing what I was going to say next, speak. They taught me how to stand with another person and listen to them speak and know that whatever reply I provided was going to be a good reply as long as it was thoughtful and honest and accepted whatever they had just said.

These classes taught me how to experience the state of flow, which is a state where you are so occupied by an activity that you are living entirely in the present tense. You aren’t aware of the past or the future. You aren’t judging yourself or the other person. You aren’t searching for the good words. You are without hope or fear. You are allowing yourself, and your partner, to just be.

My advice is to stop trying to think of words. Turn off your brain. Think less. If you need to tell yourself that you are in no way flirting, then tell yourself that. Other folks tell you to curate your personality, give you examples of questions to ask, tell you to lick your lips, twirl your hair, touch his arm, be aggressive, be demure, figure out whatever it is he wants and be precisely that.

You need to know, deep in your bones, that you can flirt. You have flirted in the past without even knowing it. The essence of flirting is to show the other person that 1) you find them interesting, and 2) you’re available. These messages are usually transmitted wordlessly.

You know what the best flirters do? They don’t think. They hold their bodies in a way that feels comfortable. They open their mouths and they say whatever occurs to them. They know that what they say does not matter. They know that the stakes are low, and if this person doesn’t like them, someone else will. They trust that it’s going to be OK no matter what they say, and it always is.

The next time you’re standing at a bus stop with a man you like, do the thing that you want to do. Look at him. Open your mouth. Say the words that come and smile.

Dana Norris once went on 71 internet dates, many of which you may read about here. She is the founder of Story Club and editor-in-chief of Story Club Magazine. She has been featured in McSweeney’s, Role Reboot, The Rumpus, and Tampa Review and she teaches at StoryStudio Chicago. You may find her on Twitter at @dananorris. 

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