When Flirting Gets Awkward

Author: Kristina Cappuccilli

You're awk. Go away.

There are few things that annoy me more than an awkward flirter. I’m not sure why, at 23 years of age, I encounter grown men who STILL have no idea how to speak to women.

And for all the saps out there, I will not feel bad about it. I will not have sympathy and I will handle it in the quickest possible way that gets me out of any interaction with said flirter. I should learn to have patience for a million things—waiting at the doctors office, the color wheel on my Mac taking a year and a half, my nails to dry before I straighten my hair—but awkward flirting is not, and will never be, one of those things.

I’m sorry, but it’s just not going to happen.

Now that I’ve drilled my own harsh perspective into the ground, let’s focus on the real problem. Why do men find it so hard to approach women? Are they only intimidated by us when they find us to be more attractive than themselves, or is “Fuck Off” permanently tatted on our forehead? Are we more approachable when we’re in a group of girls or when we’re alone? Do we give mixed messages that leave them dizzy with confusion? Is it hard to distinguish between a sexy wink and a stray eyelash landing in our line of vision? Do they have images of Ryan Gosling and James Franco running through their heads because they know they can’t live up to these expectations of what women might want?

I understand that, as a gender, women are difficult to handle/interpret/analyze. We say no when we mean yes, we say “we’re fine” instead of being honest about what’s bothering us, we ask if we’re fat but only seek the obvious answer—we’re a complex species. But when you’re first meeting someone, shouldn’t that be the time when things are the least complex? Sure, first conversations never run as smoothly as they do in romcoms starring Channing Tatum, but the dialogue is pretty basic; or at least it should be.

And therein lies the root of the problem that awkward flirters face. They put so much pressure on the preliminary rounds of dating that they don’t make it past Door #1. Introductions should be short and sweet. By the end, it should leave you curious and wanting more. Some guys just don’t seem to grasp this concept, because I can’t tell you how many times I’ve been approached in public and watched some poor fool allow himself to discuss past relationships, family life, and embarrassing fun facts approximately 7-10 minutes into a conversation with a perfect stranger such as myself. It’s happened to all of us. While we’re waving a red flag and downing the rest of our vodka tonic, they’re asking for a cell phone number they’re never going to receive.

The whole thing is so sad that I almost feel sorry for them, because maybe they just don’t realize what they’re doing. Maybe they’re out of their element and intimidated. Maybe they figure that girls want “open and honest” in all forms of the phrase. Maybe they need another (half dozen) cocktail(s). At any rate, I’m going to take this time to round up all of the advice I can think of in order to help those charmless fools with no game. Here it is—the list.

1) Never use corny lines. They never work, unless your sarcastic wit is at an all-time high. Then again, if it were, you probably wouldn’t need to use corny lines in the first place.

2) Pretend we’re wearing turtlenecks when you’re speaking to us. It’ll make it easier for you to stop staring at our tatas.

3) Try not to offend us in the first 60 seconds. Trust me, it’s happened.

4) Don’t try to dance with us when we pass up the offer the first time around.

5) Unless you’ve mastered the sexy, gentlemen-like “lower back palm press,” no touching.

6) Avoid bringing up personal issues that leave us speechless and uncomfortable. For instance, some topics you might want to avoid are: death, crazy ex’s, STDs, getting arrested, to name a few.

7) If we’re talking to our friends, don’t try and involve yourself in the conversation. It’s always annoying.

8) Apparently the art of passing notes didn’t die in middle school, so please refrain. I couldn’t make this shit up if I tried.

9) We love getting compliments, but telling us we’re beautiful in accordance with the amount of times a normal human being blinks in a minute is just too creepy much.

10) Quit being cocky. It’s obnoxious, a waste of time, and couldn’t be more of a turn off to any woman worth approaching in the first place.

I could go on and on until I’m blue in the face, but the long and short of it is simpler than listing every “don’t” I can think of.

1) Be yourself.

2) Talk to us like we’re just another person.

3) Ask us generic questions that lead to deeper conversation (Where did you go to college? Where are you from? What’s your job like?).

4) Make us laugh.

5) Listen to what we’re saying.

6) Limit the compliments so they don’t seem fake or forced.

7) If we give you an inch, don’t try and take a mile.

8) Don’t assume we’re single, and respect the answer we give you.

9) Pay attention. Read the signs.

10) Don’t pressure us. If we’re interested, we’ll definitely let you know. If we aren’t, leave off on a positive note and move on.

We have faults too, you know, and sometimes first impressions are a little off. Above all, keep it simple. Short and sweet is always the best option. Well, most of the time anyways.

Kristina Cappuccilli

20-something creative writer turned corporate, armed with big ideas and even bigger dreams. Avid reader, lover of all things musical, incessant blogger. Sucker for movie quotes, feature writing, and a good book. To inspire and be inspired.

5 Comments
  1. Makes me feel better about being my normal self around women. I hang out with a lot of friends that check a few things off of that “don’t” list at least once or twice in any given social situation. Needless to say they are all single “and looking”. Thanks for the post! 🙂

  2. Of course! I’m glad I could shed some light on the topic : ) When first meeting someone, most girls want nice conversation and a good laugh. We don’t expect the world–so don’t feel pressured to be someone you’re not! Simplicity is key.

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