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A Guide to Flirting with Men for the Socially Awkward

Being a woman in 2015 is a tough job. We are constantly judged and criticized as a group for stereotypes that are well beyond our control and this has led many of us to shy away from certain aspects of that curious courting ritual called flirting. Being called “a flirt” is even considered somewhat of a put-down and that needs to be changed.

Flirting (and being flirted with) are the first steps down the long road to self-confidence and nothing is sexier than a confident woman.

Not convinced?

When was the last time a human being told you something nice out of the blue? Granted, there is a good chance that it was an elderly woman complimenting your complexion or a child commenting that you smell like a delicious food and I sincerely hope that it wasn’t flirting, but the most important idea here is that flirting is a compliment and compliments make us feel awesome.

It is obvious, however, that flirting and being flirted with will not instantly make you an invincible emotional superhero capable of smiting uncomfortable feelings with one blow, but it may make you accept that as a possibility for the future (after the whole traumatic radioactivity dies down anyway…)

So, unsurprisingly, the first step to flirting is to get decent at giving genuine complements. As a society, we don’t really complement each other. It is a social gesture left almost entirely to cat-calling construction workers and creepy old men, but not anymore.


The idea behind it is two-fold: to get comfortable in an uncomfortable area (i.e. saying something nice to a stranger) and to get comfortable making people uncomfortable. Social interactions are a skill and skills must be practiced.

Remember that. And for the most part, no one practices. We either are already decent at it or we avoid eye contact almost entirely. But all of those lumbering humans out there are just like you. They get nervous and sad and poop sometimes. Go say something nice! They might even say something nice back.

After your compliment skill has increased a bit, the next step in the flirting process is to get comfortable with a modicum of human contact. Next time you are busy complimenting the grocery store checkout guy on how delicately he handled your eggs, reach out and touch his arm.

Especially in America, our social interactions have lost that small amount of personal-space violation necessary for a personal connection. Just keep in mind that touching in the workplace can violate your company policy, so be sure to keep it professional.

Now that we have made past complimenting while touching, it is time for the actual flirting to commence. The biggest difference between a regular compliment and one made in flirtation is context.

If your hair dresser compliments your shiny curls; they are probably only interested in you for your repeat business. If a handsome stranger tells you that your hair is gorgeous, they might be open to a bit of flirting.

how to flirt with a guy

After you have selected your intended flirting target, there are a few things to keep in mind:

  • Prep in advance to keep your confidence as high as possible- If you feel sexy in your outfit, if your breath smells like a Scope commercial, if you are clean; you will have less of a chance for the ultimate buzz-kill of insecurity to creep in and kill the mood.
  • Be as sober as possible- Drinking may be portrayed by Captain Morgan as the easiest way to be great at everything, but even if you aren’t uncomfortable, your future love-interest might be put off by a visibly intoxicated you.
  • Admitting to being nervous to talk to someone can be an ice breaker and tension reliever. Men tend to find a touch of vulnerability attractive anyway.
  • Keep your compliments sincere- If you mention his cologne just because you noticed it, but not necessarily in a “good way,” keep it to yourself, and if you spot a guy, but can’t think of anything that sets him apart from the rest, be more selective. Approaching a stranger and whispering, “You look weird enough to date me,” isn’t flirting, it’s desperation.
  • Pick your venue carefully- There are most definitely places that people go and are automatically more receptive to flirting. A man may be more into you from the start if he is already in the “Oooh, Look! A Lady!” frame of mind as opposed to if he is, say, visiting his grandma at the hospital. Parties, bars, coffee shops, concerts, parks, sporting events- these are all great social places to meet folks who might be in the mood for meeting someone new.
  • Start small- Most socially-inclined men are aware enough of the delicate nature of human relationships to understand that if a woman strikes up a conversation, she may be trying to find him attractive. He will also have some idea that if he is there with someone else, he’d better mention it, before she finds out. So, it is always a good idea to ease into the flirting gradually, just in case.
  • Last, but not least, keep in mind that flirting, although it takes some practice to perfect, is a natural social response to an attractive person. Just like the peacock has its feathers, we have buckets of charm. Starting the conversation is the hardest part; the flirting is just the frosting.