ASK THE DATING COACH: How to Confidently Approach Women. Plus: Emoji Tips & (Non-Sketchy!) Pickup Lines

My clients often ask me “Why Am I So Afraid to Approach Women?”

Blame your caveman brain. Here’s how to become fearless when you want to meet a gorgeous girl.

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“Connell, I have a successful business, and I’m confident in most areas. Why am I petrified to approach a pretty girl?”
~ Ken, Cleveland OH

I’ve coached some truly brave men—a veteran who saw combat in Iraq, an aerial firefighter whose DC-10 Tanker douses wildfires out west. Hero stuff. Yet when I met them, these guys couldn’t talk to a cute girl waiting for her Starbucks chai latte. 

Why? Blame evolution. Some 100,000 years ago, when our ancestors lived in small groups on the savannahs of East Africa, approaching the wrong woman meant possible death, says evolutionary scientist Jeanette J. Kuhn, Ph.D, of Columbia University. “If the tribal leader thought you wanted his woman, you could get brained with a rock or be expelled from the tribe,” Behe told me. “Either way, it was a death sentence.” 

Today, we basically have the same brains as early Homo Sapiens, Kuhn explained. So when you walk up to that stunner at the bar, your fight-or-flight response kicks in. Cue the sweat, racing heart and dry-mouth. 

The solution? Approach anyway, and show your brain that there’s no risk. Some of my clients’ hands are shaking when they talk to that first woman of the night. An hour later, they’re laughing, flirting and setting up dates. 

Ken, the anxiety you feel about approaching will subside when your brain realizes there’s nothing to fear. There are no guys with rocks—just guys with bottles of Rolling Rock who’ll watch in envy as you chat up the sexiest girls in the bar.  

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“I’m average-looking. Can I get a beautiful girlfriend?”
~ Craig, Indianapolis IN

As a fellow average-looking guy who’s never mistaken for Chris Hemsworth, I have good news. Looks, height, money—they just don’t matter.

While men are entranced by physical beauty, women (lucky for us) go deeper. They want intelligence, substance, or a good laugh. 

Consider: 

  • Pete Davidson + Ariana Grande
  • Jeff Magid + Emily Ratajkowski
  • Billy Joel + every woman he’s ever dated

Unplug from the fiction that you need to be ripped, rich and 6’4’’ to get a gorgeous girl. 

Now, you can be average-looking, but you can’t be average. You must be exceptional in some way. You need swagger or wicked wit or be able play an instrument. 

But even then, you don’t need moves like Mick Jagger. Aim for Mick Fleetwood. He dated Stevie Nicks in her “Rhiannon” youth.

Google mid-‘70s Stevie and ask yourself: Wouldn’t you love to love her?

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“I’m a grown-ass man. Do I have to use emojis when texting women?”
~ Marc, Beverly Hills CA

Yes, you need good emoji game, especially if you’re dating women under 30. Millennials love emojis almost as much as they love brunch and complaining 🥂🥞. 

Attraction is about good emotions, and emojis make girls 😁 from👂to👂. So if you’re not using them, you’re being a 💩+👨.

(See? I called you a sh**head, but emojis made it adorable!)

Follow my 7 Emoji Rules and you’ll soon have the 🔑 to her ❤.

1: End your first text with a 😉. In real life, winking falls somewhere between creepy and restraining order, but in emoji-land it’s sweet. 

2: Limit yourself to 1 or 2 per message. You want to sound like a man who’s emoji-fluent, not like a tween girl. An exception… 

3: If she sends you a sexy selfie, reply with multiple 😍😍😍. A woman likes knowing her beauty is affecting you.

4: Use the Rule of Three. It’s a trusty comedy-writing tool in which the third element in a list gets a laugh because it’s surprising. Example: After your first date, text her, “Kayla, drinks were fun last night. Let’s do it again🍸👫🐸” A random frog is funny! And funny = another date. 

5: Only send 🍆 as a joke. Guys get sexty way too soon, so show that you’re a gentleman and that you have a sense of humor. “Allie, I’m fresh out of dick pics so 🍆 will have to do. You’re welcome.” (If she replies with 👐🍑, propose immediately 💍.)

6: Use puns. Yes, they’re low-hanging 🍓🍏 in normal discourse, but puns pack a punch when paired with emojis. Don’t say “yes” when you can say “dolphin-ately! 🐬” She’ll love it. Because dolphins are adorable. And adorable = another date.

7: Break any of these rules after you two have sex for the first time, and let her know it was wonderful:”🍆 🌋 🌋🌋🌋🍑🚀🎉💫 😍😍😍!!!!!”  

Happy texting!  😃📱🐸

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“I have a nice vibe with the hipster barista at my coffee shop, but it’s hard to ask her out because she’s always so busy. Advice?”
~ Curt, Pittsburgh PA

The fact that she’s up to her tattooed neck in lattes may seem like a challenge, Curt, but her hectic workplace gives you an advantage over other guys. You’re not the first customer who’s gone for her digits, but you’ll be the first who gets that she’s under the gun, what with the line of people waiting for a hot-drip injection.

A woman notices subtleties in a man’s behavior, so you’ll raise your stature by being the guy who understands that she’s swamped. After she hands you your mocha-frapp, say: “Kelly, you’re busy caffeinating Pittsburgh right now, but it would be great to talk when you have more time. How about a drink this week?” 

She’ll be doubly impressed—that you took a risk, and that you have social grace. And social grace is sexy.

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“My last three dates: friend zone, friend zone, friend zone. Why do women just want to be buddies with me?”
~ Anonymous

I feel your pain, Anonymous. I didn’t just live in the friend zone—I owned vast tracts of real estate there. 

The thing is, women don’t banish guys to the friend zone. We send ourselves there. 

Every social interaction has a “frame”—that is, all the unsaid assumptions and communications that inform the dynamic. When you’re on a date, there are two possible frames: either “friend-to-friend” or “man-to-woman.” Think of them as TV channels.   

The friend-to-friend channel looks like this: You play it safe. You talk about surface topics, rather than getting personal. You barely touch her. It’s a “nice” conversation, but there’s no polarity, no sexual tension, no spark. 

The man-to-woman channel? You’re expressive. You make laser eye contact. You compliment her sexiness one minute and tease her for being nerdy the next. You both share your passions, fears, aspirations. You lean in, brush her hair out of her eyes, whisper in her ear, and when the time is right, kiss. 

See the difference, Anonymous? If you behave friend-to-friend with a woman, that’s how she’ll feel about you—as just a friend.  

The fix is to tune to the man-to-woman channel. It starts with expressiveness. Lose the filter. You can and should be a gentleman, but speak your honest thoughts. If she looks sexy, tell her. If you like her, let her know. If she’s nerdy, tease her. Girls like when you pull their pigtails.

So grab the remote and start flipping. It’s like going from the Disney Channel to Vicky Cristina Barcelona.

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“What’s the best pickup line?”
~ Chris, Chicago IL

The pickup line is a myth, Chris, like the Yeti or graduates of DeVry University.

You can’t pick a girl up with a line. But you can open a conversation in a way that creates attraction. 

The best “pickup line” is whatever true thought you have the moment you walk up to her.

I learned this a decade ago on a rooftop bar in New York City. I’d been experimenting with “cool” opening lines, and nothing was working. I saw a Zooey Deschanel lookalike and, though I was nervous as hell, I decided to try something radical: being authentic.

She was sitting on a couch, and as I slid in next to her, I shared my truest feeling: “Hi. I’m actually really shy, but I had to meet you. I’m Connell.” Huge smile, her blue eyes widening. “Oh, suuure, you’re real shy. I’m Amy.” She was instantly into me. 

The crazy thing is, by owning my nerves, I came across as confident. My lack of smoothness was somehow… smooth. It was like that Seinfeld episode when George attracts a beautiful blonde by doing the opposite of instincts.

Women have heard all the lines. If you parrot what some “PUA” teaches, you’ll sound like a million other guys, and you’ll water down your most attractive trait: your personality. But if you speak from your heart, you’ll be truly authentic. An original. 

So if you want a line, try this: “Hi, I’m Chris, and I wanted to meet you.” Simple. Vulnerable. Powerful.

Go full Costanza. Do the opposite.

~ Connell Barrett