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First-Date Advice for Deeper Connections

Dating coach Connell Barrett dishes out first-date advice. He answers your questions on how to have great first dates, 3 smooth moves to get the first kiss, and the way to “keep things casual.”


I need some first-date advice. What are the most important things to keep in mind? Because when I walk into a first date, I have no idea what to focus on. I need some clarity. 

—Martin, 39, Phoenix

Here’s some simple first-date advice: Follow the three P's: be positive, present, and playful. 


If something awful happened that week—you got laid off, your dog died, Nickelback announced a reunion tour—hey, sorry, but don’t bring any negativity to the date. You want to bring a warm, positive vibe to the date. No baggage allowed. 


Get into the moment with her, rather than worrying about what you just said or what you’ll say next. When you’re truly present with a woman, listening to every word she says, your most charismatic, confident self arises. The right words come. Women love a man who can get in the moment. Give her the present of your presence. 


Few men harness this secret weapon. A first date is supposed to be a good time, so be as fun and playful as you can. Crack jokes. Tease her a bit. Suggest a fun game, such as Two Lies and a Truth or Would You Rather. The more fun she has with you, the more she’ll enjoy the date—and likely want to see you again. 

A bonus piece of first-date advice: Ask thought-provoking questions, such as, “What would you like as a kid?” or “Who would play you in the movie of your life?” In a 2017 study, researchers at Harvard found that people who asked questions on first dates were seen as more likable and attractive than those who didn’t ask questions.

As the old saying goes: To be interesting, be interested. 

couple kissing


Help! I’m pretty good on dates, but when it comes time to moving in for the kiss, I get shoved in my head and wimp out. Women blow me off because I don’t “man up.” It sucks. What’s a smooth way to go for the first kiss?

—Bradley, 35, Toronto 

I used to struggle with this too. I felt stuck: Do nothing and you’re in the friend zone. Do the wrong thing and your kiss gets rejected. 

Here are three smooth ways to go for that first kiss, in ways that women love—and that usually get her kissing you right back. 

1: The “Close Your Eyes” Kiss

So, you’re deep into a first or second date. Look at her, smile, and say, “Close your eyes.” If she closes them, that’s a green light. Kiss her. If she doesn’t close her eyes, no sweat. Try later. You’ve put the idea of kissing in her mind, which increases sexual tension—and you didn’t get the cheek.

2: The “Shush” Kiss 

As she’s talking, look down at her lips, back at her eyes, and then at her lips again. Smile, softly “shush” her, lean in, and kiss. Post-smooch, say, “I’ve been wanting to do that all night. You were saying?” Odds are, she won’t be able to remember. 

3: The “You Know What Happens?” Kiss 

This move helped me a lot when I was getting great at first dates. As she talks about herself—perhaps sharing a funny story from her past—listen for a detail that stands out. Next, use that detail as the “reason” for kissing her, by saying this: “You know what happens to girls who [thing she just said]? They get kissed.” Then move in. This lets you transition from the topic to the kiss, in a way that she sees coming.  

It will go something like this: 

HER: “And that’s how I got locked out of my own house on Christmas eve. Crazy, right?”

YOU: “Well, you know what happens to girls who get locked out on Christmas?”

HER: “What happens?”

YOU: “They get kissed.” And you move in.

Tip: Don’t overthink this. Almost any detail that she shares can work, as long as it was just said. 

“You know what happens to girls who like skydiving?”

“You know what happens to girls who hate the Beatles?”

“You know what happens to girls who are clumsy?”

The answer is always the same: They get kissed. 

Do this well and some women will actually say, post-kiss, “Wow, that was smooth.”

couple on a bed


I want a great relationship eventually, but I also want to “sow my oats” for a while. How do I let a woman know I just want something casual?

—Clark, 33, Cincinnati

My mission is to help good men get great girlfriends by being authentic, but hey—there’s nothing wrong with sowing an oat or three on the path to a fulfilling relationship. 

Be honest and clear about what you’re looking for. Let a woman know no later than the first date that you’re seeking something casual. Say something like, “I’m looking for a great connection, but I don’t want anything serious with anyone at the moment.” Stress the “with anyone” part. Let her know this is where YOUR head is. It’s not about her.  

Of course, never let her think that you’re open to a relationship when you really want something casual. 

Remember—it’s casual, but it’s still sex. It can be powerful, emotional and important for one or both of you. So always be kind and compassionate. You can be casual but still caring. 

Not sure what to text a girl or need flirty first-date questions to get sparks flying? Read Connell's Ask The Dating Coach column. Ready to learn what to do on a second date? Click here. Ask a question below to subscribe.

Connell Barrett is a NYC dating coach helping men all over the world find the women of their dreams through authenticity. Connell's appeared on The Today Show, Access Hollywood and more. He's also been featured in O Magazine, Maxim and Cosmopolitan to name a few. His dating book, Dating Sucks But You Don't: The Modern Guy's Guide To Finding Total Confidence, Romantic Connection, And The Perfect Partner comes out in Spring 2021. Ask Connell a dating question below.


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Connell Barrett Dating coach for men

I'm dating coach Connell Barrett. I help men build confidence and connect with women by being authentic!

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NYC Dating Coach Connell Barrett

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