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What To Say When Asking A Girl Out

Dating coach Connell Barrett answers your questions on what to say when asking a girl out, 7 style secrets, and the power of being “Radically Authentic."

What To Say When Asking A Girl Out

Connell, I’m pretty smooth when texting women, but when it comes to what to say when asking a girl out, I always get stuck in my head. Can you give me some advice on what to text?

—Rick, 36, Cincinnati


Don’t worry about finding perfect words, Rick. You’re asking for a date, not writing Shakespearian prose. (“To Netflix or to chill—THAT is the question…”)

Here are some outrageously simple tips on what to say when asking a girl out—whether asking via text, on the phone, or in-person.

1. Never say, “So, what do YOU want to do?” Women love a man with a plan. Lead.

2. Suggest your date idea with confidence (“I know a place you’re gonna love . . .”), but make sure to listen to any objections she might raise and adjust accordingly.

3. Harness the power of the word “let’s," which allows you to lead in a non-bossy way (“Hey, let’s grab a smoothie . . .”)

4. Choose a location that’s convenient for her to get to.

5. Frame it in a way that assumes she’ll say yes if she wants to. So, no phrases like “. . . unless you don’t want to” or “. . . if you have time.”

6. Don’t start tossing out possible days for the date. If her schedule is busy, she’ll have to keep turning you down (“How about Monday? . . . Okay, Wednesday? . . . Maybe Thursday?”), which makes you look too available and too eager. Instead, give her a window of time, and use this magical phrase: “What day(s) works for you?” This way, she’ll tell you when SHE’S free.

7. Add a sweet, sincere comment such as, “It will be cool to finally meet you.” Remember: It’s not about the wine or the karaoke. It’s about the two of you getting closer.

When you put it all together, asking her out will sound something like this: “Hey, Rebecca. You like red wine, so let’s grab a couple glasses this week. I know an awesome spot not far from you. It would be cool to see you. What night works for you?”

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7 Style Secrets That Let You Dress to Impress

I have a bad feeling that my style bites. A little help?

—Renaldo, 40, Phoenix

What to Say When Asking a Girl Out. Fashionable man 

The right clothes help unlock your confidence. In a Men’s Health survey, 78 percent of women said that dressing well is the hottest thing a man can do. In addition, 85 percent said that a well-dressed man is sexier than a man with lots of money.


Here are seven style rules for first dates (and dating in general.)


1: Your shirts, pants, and jackets should be tailored for your body, or appear to be. The biggest style mistake men make? Baggy, ill-fitting clothes. Your duds shouldn’t be too tight, nor should they billow. Think somewhat snug.

2: Own at least one pair of quality, dark denim jeans (blue or black). And please, no pleated khakis! Be a hot guy, not a Helpful Honda Guy.

3: As for shirts, favor button-downs, polos, and quality tees. In an Esquire survey, women preferred plain white tees on a man more than any other kind of shirt.

4: Have at least one pair of fun, stylish sneakers (NOT gym shoes), such as Stan Smiths or Chuck Taylors. As for dress shoes, consider a classic loafer, brogue, or lace-up Oxford (brown or black.)


5: Be well-groomed, and smell absolutely amazing.

6: Your hair (or lack thereof) should look “on purpose,” whether you’re rocking a cool fade, or shaving your head. Consider a consultation with a hair stylist. If you’re balding, keep it very close-cropped, or go full Kojak.

7: Wear boxer-briefs. In a GQ survey, 65 percent of women preferred boxer-briefs on a man (compared to 19 percent for boxers and 5 percent for tightie-whities.) True, it’s only the first date, but it’s best to be prepared.

How To Keep it REALLY Real: Radical Authenticity

Radical authenticity

I watched one of your videos about being “Radically Authentic.” I like the sound of that, because I don’t want to be some fake, weird “pickup artist” guy. Could you go deeper about what that means?

—Nish, 31, Stockholm, Sweden


Being Radically Authentic is about removing the masks that men wear with women and showing her your best, most real self.

I wore many masks over the years. For example, take my interactions with a woman named Lisa. I met her back when I was searching for what worked with dating. I was way into her. She was the perfect combination of smart and sexy, and had some wicked one-liners. After our first date, I was schoolboy smitten, all but scribbling “Connell + Lisa” on a spiral notebook.

But I felt out of my league with her—a Toledo Mud Hen playing in Yankee Stadium. What would a bright bombshell like her see in a bookish nerd like me? She was into SCUBA and hiking, and so on our second date I pretended to be the rugged, outdoorsy guy I thought she wanted.

Which is to say, I made a bunch of shit up. I told her I was studying to get my pilot’s license (lie), loved skydiving (double lie), and swam with sharks in the Caribbean (double-dog lie.) I have a terrible poker face, and as I spun these tall tales, my forehead became a Slip-n-Slide of sweat. After that date, she friend-zoned me, of course. Because when you feel unworthy and pretend to be someone you’re not, women can tell.

You need to remove the mask.

Yet when you’re authentic, you’re at ease, making you more confident and attractive. Also, you give women a singular experience. After all, you’re not one in a million. You’re one in seven billion. It’s the difference between a watered-down wine spritzer and a strong Scotch.

Women want to catch a buzz on the good stuff—the top-shelf, 80-proof, barrel-aged you.

Here are the (drumroll please….)

5 Pillars of Radical Authenticity


Never lie to women and never present a false front. Share your sense of humor, your points of view, your passions. The more honest you are, the more you accept your authentic self.


Let your flaws, fears, and mistakes show while fully owning them. It takes strength to be vulnerable, and women love strong men.

Taking Action

Align your actions with your words and values. As Shakespeare wrote, “Action is eloquence.”


It’s the thing women want most in a guy, according to a 2019 survey of 64,000 single women. So be nice.

Growing and Giving

In dating and in life, the more you grow, the more you give—and the more you give, the more women want to give back.

In dating, Authenticity is King—forever may he reign.

Want some tips on where to go on a first date or how to flirt with women? Read Connell's column here and subscribe so you never miss an update!

Want to be coached by Connell? Order the book Dating Sucks But You Don't, and learn how to approach women and get the girl here. It comes with incredible bonuses like live group coaching!

Connell Barrett is a NYC dating coach for men. He's helped men all over the world find the woman of their dreams with actionable advice such as how to get out of the friend zone. His work has been featured on Access Hollywood and the Today Show. In addition, you can find him in print in Maxim, O Magazine, and Cosmopolitan. Ask Connell a 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

106 W 32nd St, New York, NY 10001

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