Flirting for the socially awkward: The basics


Miss Bea Haven, Consultant

Case Western Reserve University students are great at many things––remembering endless protein structures and equations, overloading our work schedule while still managing to get everything done, and even functioning effectively on a miniscule amount of sleep.

Unfortunately, our students seem to be lacking in one specific department––namely, their ability to flirt.

After last week’s article on cuffing season, I received a number of comments agreeing that as a student body, we rely solely on long-distance pining as our form of affection. In a perfect world, we’d be advanced enough to show interest in another person without the need for flirting. However, we do not live in such a perfect world, so your favorite relationship guru has taken up the task of exploring all things flirting in my newest three-part series. So, to all of my favorite socially awkward readers––this one’s for you.


Eye contact

Although the whole “eyes are the window to the soul” metaphor has long become a cliché, one thing still rings true—eye contact is a big deal when it comes to getting to know someone. Establishing connections doesn’t usually start with words; it starts with a glance. So if you struggle with establishing eye contact, this might be where your difficulties with flirting begin.

Look, I get it—sometimes it can feel so uncomfortable looking into the eyes of someone you don’t know well, especially if that person is someone you might have a crush on. You might feel the need to fidget or look away to ease the nervousness in your brain. Fortunately, if this is a skill that you want to get better at, there are certain methods that you can practice to gradually improve at catching (and keeping!) the gaze of someone you find attractive.

Part of flirting is having some degree of self-confidence, and nothing says self-confidence like being able to look at someone straight in their eyes without hesitation or nervousness. Now, this is easier said than done, and if you don’t have this kind of certainty yet, that’s fine! The “fake it till you make it” method works too. If you can’t hold someone’s gaze for extended periods, try looking from their eyes to an imagined dot in the middle of their face. This gives the illusion of a mutual gaze without all of the pressure of actual eye contact. Another alternative is laughing at their jokes to give yourself a chance to chuckle while looking at the ground. Not only will this make your crush feel funny, but it also allows you to break eye contact when you need to.

In the long term, try desensitizing yourself to the act of looking at strangers in the eyes. Instead of staring at your phone and avoiding an acquaintance while walking through Tinkham Veale, make eye contact, smile and nod. When checking out, look at food workers, shop clerks, coffee baristas, etc. This will give you small, achievable goals by which you can measure your success. You’ll find that once you have mastered that ability, batting your eyelashes at a crush is only a little more challenging.

Once you’ve got basic eye contact down, there is a whole world of flirting at your disposal. Maybe you want to master the seductive up-down glance or try out the casual side wink. It might seem uncomfortable at first, but in time, you’ll find these flirty behaviors can become a useful part of your social repertoire.

My final piece of advice? Don’t forget to blink!



After almost two years of on-again-off-again isolation, it is no surprise that we are struggling to connect conversationally with each other now more than ever. If you naturally prefer small group interactions or have a low social battery, you have an even greater uphill battle when it comes to conversational flirting.

Fortunately, I have a technique that really helps whenever I need to navigate a chat session or flirtatious banter. In your mind, picture having a conversation as a giant tree.

I know it’s weird, but bear with me.

When chatting with a stranger, you usually start off with small talk and surface pleasantries. In my mental metaphor, this is the thin branches at the crown of the tree. They are easy to break and not exactly something you want to grasp onto when trying to flirt. Luckily for you, tree branches never grow alone––they are always connected to a branch, which is connected to another branch and so on. By using these connecting topics, small talk can allow you to get a better understanding of any person while also not being overwhelming or too serious.

An example: you’re at a gathering and your friend introduces you to someone you might be interested in. They’re attractive and seem nice, but you don’t know them well enough to start an in-depth conversation. Here you might ask something like, “How do you know (insert friend’s name here)?” This casual question doesn’t carry a lot of weight by itself, but it connects you to a larger picture of your counterpart’s interests. If they respond by mentioning a school organization, a class or even the year they met, you now have a slightly larger connecting branch that you can build upon. From there, you can ask any number of questions, as long as they segue from the branch that was connected before it.

Using this technique, you can connect any small topic to something larger and more meaningful. Does someone start a dreaded conversation about the weather? Discuss how the snow in Cleveland compares to your hometown, and afterward, ask about their hometown. With each question, you strive towards your ultimate goal of getting closer to the base of the tree, i.e. getting to the core of the person you’re trying to get to know intimately.


Body language

Once you grasp the nuances of having a conversation, you can move on to body language. Of the flirting basics, body language is probably the most difficult to fully grasp. Everyone is different, and one person’s obvious flirtation could be another person’s version of just being nice.

Basic flirtatious body language includes body position, voice tone and physical touch.

Body position is probably the most instantly recognizable indicator of interest. Next time you are in a group with someone you are interested in, look at how you’re positioned. Are your feet angled towards them? Do you accidentally catch yourself looking in their direction more often than not? Do you find yourself turning to listen better? These nuances are not exclusive to just you, I promise. Even unwittingly, we have a tendency to focus on the things that we like. It’s kind of like how your eyes tend to wander towards the dessert area of a buffet, even when you haven’t started eating your dinner.

When trying to understand body language, you can learn just as much by watching and listening as you can by doing. For instance, did you know that women tend to pitch their voices up when flirting with someone they are interested in? Even I notice that I put on my pleasant “phone voice” whenever I’m interested in an individual. On the other hand, men tend to pitch their voices into a lower octave when they are feeling flirtatious. So be aware of anyone talking differently in your presence—maybe they have a cold, or maybe they are engaging in the oldest form of flattery.



Speaking of flattery––compliments! Give them, and lots of them. You will rarely go wrong with a respectful compliment. Even if people don’t interpret them as flirting, you still make others feel good in your presence, which is the easiest way to attract people.

A good formula that I like to use for complimenting women is an exciting adjective plus something she chose for herself. “Oh! What a great new hairstyle,” or “Wow, your blue eyeshadow is so cool!” As long as you stay away from surface compliments and comments on her body, you should be good. When complimenting men, on the other hand, you can get away with just about anything. Socially, men don’t receive nearly as many compliments as women, so anything from “Oh wow, have you been working out lately?” to “You look great in (insert color here)!” could make his day. And if you’re a man reading this article, don’t forget to compliment the homies. Flirting is good, but hyping up your friends is even better.



As much as I hate adding to the ever-growing list of things that you need to apply yourself to, flirting is just one of those things that you have to work on in order to improve.

When I was younger and far more awkward than I am today, I would actually practice my chatting skills. I would visit the touristy part of my neighborhood and chat with anyone I thought looked open to a conversation. Most visitors were only there for a short period of time, so there was little risk for further embarrassment if I botched any flirting attempts. These areas were also the most secure areas in the city, so I never felt like I was in danger if a situation turned uncomfortable.

Although these interactions usually ended in rejection at first, I slowly got better. I could feel myself beginning to understand how to navigate a conversation effortlessly and how to pat someone on the shoulder without feeling like a dad at a little league baseball game.

Social skills are like any other muscle––you have to exercise them in order to get better.