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The Art of Sending Opening Messages

Dating coach Connell Barrett answers your questions on writing opening messages, how to meet women at coffee shops, and secrets to better first dates.

OPENING MESSAGES

On dating apps I struggle to get women to reply to my opening messages. I usually go with, “How are you?” or “Great to connect.” Are those bad openers? Is it me? Help! 

—Ian, 27, London

Ian, when your opening message goes unreturned, it can hurt. It makes you feel rejected and frustrated, right?

But it’s not you. It’s the lack of personalization in your opener. 

Women get messages like “How are you?” and “Great to connect” all the time. They’re as common as a penny, and as boring are as watching someone else watch paint dry. A generic “Hello” opener has no relevance to the woman you’re writing. 

The fix? Make it personal and relevant to her. 

We’re all self-interested, so use that to your dating advantage. Look at her profile, and make your opener either about her or a topic that interests her. Notice what she’s passionate about—say, her bulldog or the Beatles—and ask her about it. And if you share the interest, let her know. Commonalities = connection. 

Oh, and use her name. Everyone’s favorite word is their first name. I know mine is. (My second-favorite word? Argle-bargle, which means nonsense. It’s just fun to say!) 

A great opening message will go something like this: “Renee, I see you’re a Beatles fan. So am I. OK, question… are you more into John or Paul?”

That opening message will interest her because it’s personalized, and it’s about something relevant to her. There’s no way she won’t reply.  

And that’s no argle-bargle. 

opening messages on dating apps
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COFFEE TALK

I was at a coffee shop last week, and a red-headed hottie sat down across from me. I wanted to talk to her, but I didn’t know what to say. I was tongue-tied. I didn’t do anything, and I felt like such a loser. What do you say to girls at coffee shops? 

—Benny, 44, Indianapolis

Before I give you a practical tip to help you break the iced coffee, first things first: Forgive yourself. Approaching an attractive woman is harder than advanced calculus. Pounding heart. Sweaty palms. Fear of rejection

I’ve been there many times. Over a decade ago, a similar incident happened to me that changed the course of my life. 

On a sunny Sunday afternoon, I was in my local Starbucks, and I saw a gorgeous brunette seated by herself. She looked like Katie Holmes, who was my celebrity crush at the time. There was even an empty seat next to her. I could have EASILY sat down and said… something. Anything! I even began walking toward her, but I wimped out and kept my mouth shut. 

A conflict raged within me. There was an angel on one shoulder rooting me on, but the devil on the other side was talking me out of it.  

ANGEL: What a babe! She’s your type. Go talk to her!

DEVIL: No! She might think you’re creepy. 

ANGEL: Creepy? You’re successful, smart, and your mom thinks you’re handsome. You’re a catch. 

DEVIL: If she rejects you, it will hurt. A girl like that only dates outgoing guys, not nerdy introverts like you. 

ANGEL: Don’t listen to him. Go up to her and tell her…AAAAAHHHGGG—

[Devil impales angel with pitchfork.] 

I did nothing, of course, and she left—and I beat myself up for hours. The very next day, I hired my first dating coach to teach me what it takes to approach and attract women IRL. 

Oh, and after a lot of effort and work, I returned to that same coffee shop, met a total cutie who was waiting for her latte, and we dated for a while. 

I left Starbucks that day feeling amazing. I came, I saw, I conquered, I got coffee. 

Veni, vidi, vici… venti! 

So, what led to my success? I accepted that rejection was possible, and I decided to do it anyway. 

You see, Benny, you’re not REALLY asking, “What do you say?” You’re actually asking, “What do you say to avoid rejection?” What stopped you from talking to the coffee-shop cutie isn’t lacking the right words. It’s lacking the willingness to be vulnerable to “rejection.” 

I won’t lie: No opener guarantees that a coffee-shop conversation will go well. No opener is 100% rejection-proof. Yes, you might get shot down. 

But you also might get a number and a date and fall in love and make lots of babies. 

The only way to find out is to stick a pitchfork in that little devil, listen to your angel, and decide to talk to the pretty girl. 

Now, all that said, I DO want to give you a way to open a conversation that usually goes well—I’d say about 80% of the time. Here’s what you do. 

Pay her a sincere, specific compliment—say, about her style, the book she’s reading, her choice in coffee... almost anything. Notice something cool or awesome about her, and tell her—with no expectation or attachment to her “liking it.” 

Say something like, “Excuse me, but I really like your Rolling Stones T-shirt. I’m a Stones fan myself. You have great style.” She will likely respond well. 

Compliment openers work well for three reasons: 

1: They tend to get a warm response because, hey, who doesn’t like hearing a genuine compliment? 

2: There’s NOTHING creepy about them. You’re just sharing warm, authentic energy, and women like being on the receiving end of those vibes.  

3: They relax you because you’re not “hitting on her.” You’re just breaking the ice. The more you relax, the more confident and attractive you become. 

Don’t forget—you are enough. Women like you for your authentic self, not “smooth lines.” 

Share sincere compliments with women, and you’ll soon be amazed at how easily and confidently you can chat up attractive women just about anywhere. 

HOW TO MAKE HER “CHASE” YOU

Connell, my first dates and my texting have been flat-lining lately. I think maybe I’m boring. Women find me attractive, but I don’t get many second dates. And often they stop writing me back before I even get to the date. How can I become less boring and more exciting?

—Jared, 33, Cleveland 

Sorry, Jared, I wasn’t paying attention—I was SO BORED by your question. 

Kidding! 

I’ll bet you’re far from boring when you’re hanging with your friends, right? You’re likely more expressive, teasing them and busting their chops a bit? I’ll bet that’s the case. 

Your problem? You’re playing it safe with girls you meet, monitoring every word and trying not to make mistakes. But this is exactly the WRONG thing to do, because it puts a chokehold on your best feature: your authentic personality. 

I want you to add some playful ribbing to your interactions with women. A few well-timed teases can spice up a ho-hum date or text exchange, dialing up chemistry in the process. 

A fun way to tease a girl is by giving her a pretend “deal-breaker.” Look for a small detail about her and pretend it’s a big deal, and jokingly tell her that this “flaw” disqualifies her from dating you. This makes you more of a challenge than other guys, and it can get women “chasing” you.

(Important: Do this playfully. She must know that you’re kidding.)

It will go something like this. 

HER: “I’m more of a cat person than a dog person.”

YOU: “What? No! Tell me you didn’t say that. That’s a deal-breaker. I knew you were too good to be true.”

HER: “No, I like dogs! I just love cats, more.” 

YOU: “Sorry, too late. I don’t think I can date someone who hates dogs. I’ll bet you have a coat made of Dalmatians.”

HER: [Laughing] “No, I really do love dogs.”

In addition to sparking fun banter, a deal-breaker gets her more invested in winning you over. And the more invested a person is in something, the more they want that something. 

And that something she’ll want is you. 


Connell Barrett is a dating coach for men, providing dating advice on how to get the girl. He's helped men all over the world find the women of their dreams. Whether needing help with what to say on tinder, first date advice, or even knowing what to do on a second date, Connell gives actionable dating tips. Connell has appeared on shows like Access Hollywood and The Today Show and in publications such as Cosmopolitan, Maxim, and O Magazine, to name a few. Ask Connell a question below.

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NYC Dating Coach Connell Barrett

106 W 32nd St, New York, NY 10001

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