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Flirty Questions To Ask a Girl

Dating coach Connell Barrett on flirty questions to ask a girl, why rejection is no biggie, and how to get a second date.


Flirty Questions To Ask a Girl

It keeps happening. I always hear, “You’re great, but… I’m just not feeling it.” My first dates seem to go well, but it rarely leads to a second date. I think I need to be better at flirting. What are some flirty questions to ask a girl in those first few dates?

—Bradley, 41, Ottawa, Canada

The best flirting arises in the moment, but if you want a cheat sheet of pre-planned questions to help you dial up the romantic tension, here’s some help. Here are five flirty questions to ask a girl.

“What’s the sexiest place you’ve ever visited?”

Everyone likes talking travel, but some destinations are sexier than others. (There’s a big difference between Paris, France and Paris, Texas.)

Free to tack a cheeky joke onto the end of the above question: “What’s the sexiest place you’ve ever visited? I mean, since you haven’t seen my apartment yet…”

“What celebrity do you think would be best in bed?”

This gets you both thinking about S-E-X, but without you having to ask in a vulgar way.

“What’s one thing you want to ask me but are too nervous to?”

A superpower question! This gives her permission to ask you something personal or intimate, and when you’re both being more vulnerable, it can heighten romantic connection.

“How old were you when you first felt those, you know, feelings?”

It can be intimate and bonding to talk about how it felt when the hormones kicked in. Pro tip: Go first, to see how she responds. I’ve said this on a date or two: “I pretty much began puberty when watching Jennifer Beals in Flashdance. Legwarmers still drive me crazy.” By leading the conversation, you give her the green light to open up.

“What’s something exciting you’re dying to try?”

Save this question for well into the date, after you’ve both loosened up. She may hit you with a sultry answer (“I think it’s pronounced, ‘ménage-a-trois’…”). But hell, even if she says pizza-bagels, don’t worry. She’ll send the same question your way, and you say, “Do you want my G-Rated or R-rated answer?”

The Life-Changing Magic of Getting Rejected

Arrg! I constantly see women I want to approach, and no matter how hard I try, I can never man up. Help! How do I smash through this?

—Seth, 39, New York City

man with tie - flirty questions to ask a girl

I know how it feels to want to approach a beautiful woman yet not be able to. It can feel like there’s an invisible force field that you just can’t break through.

I wrote on how to beat approach anxiety. Literally.

My new book is called Dating Sucks but You Don’t, and what “sucks” more than anything? Rejection.

Dating sucks because rejection sucks. You take a chance with your heart—you ask a girl out, you send that flirty text, you approach—and if you get turned down, you feel wounded.

But what causes the pain is not rejection itself? It’s how you interpret it. You give it a painful meaning. You turn it into evidence that you’re not attractive to the kinds of women you want to date.

You see, all men (and all people in general, really) want to feel special and important. This driving force is hardwired into our psyche. It’s why we climb mountains or pump iron. Hell, I wrote a book in part so I can tell the world, “I’m an author, bitches!” It makes me feel cooler.

One of the most powerful ways to feel special and important is through dating. Validation from the right woman can be intoxicating. It helps you realize something powerful: You are enough. And there’s nothing wrong with this.

But when you get rejected, it can make you doubt your romantic worth. You feel less special, misinterpreting that rejection as a sign that you’re unattractive. Then you extrapolate: If you’re not attractive to women, if you’re not enough, then maybe you won’t get to give or receive love, and that would lead either to loneliness or to settling—both awful outcomes.

That’s heavy stuff.

Viewing rejection through this lens turns any romantic risk into Judgment Day for your worth as a man. So you don’t take risks and approach the kinds of girls you’re drawn to, because rejection would cut deep, making you feel unattractive and less of a man.

And if you DO take a chance and, say, approach a woman you find attractive, you can’t relax and be your best self, which leads to MORE rejection. It’s a vicious downward spiral.

I want you to see rejection through new eyes.

When I take a client out for in-person wingman training, I WANT him to see me get rejected. I have him choose a scary approach situation—say, a large group of girls on the dance floor—and I go in, talking to the cutest one.

I often (but not always) get rebuffed. I do this not because I’m a masochist. My client needs to see rejection not as something to fear but as part of the dating process. It’s required.

You can’t approach women and NOT get turned down from time to time. You can’t get Tinder matches and NOT get ghosted occasionally. It’s part of putting yourself out there.

What if you saw rejection as painless? What if you were immune? What if you gave far fewer fucks? You could take new, bold actions and with lots of confidence.

I want you to see rejection for what it is: no biggie. A woman’s rejection is not—I repeat, NOT —evidence of your worth or importance. It’s merely evidence that she’s not interested. Maybe you’re very attractive but just not her type.

Rejection means next to nothing. You can brush it off, just as you do when the restaurant hostess “rejects” your request for a brunch table on a busy Sunday, or when the Delta ticket agent “rejects” your request for a business-class upgrade.

Look at dating rejection the same way. Your worth isn’t on the line. It’s not personal.

The truth is, a woman who barely knows you can’t truly reject you.

Now, if your girlfriend says, “I don’t love you, you’ve never made me orgasm, and I’m leaving you for Fabio,” okay, now THAT is rejection.

But if a woman you barely know blows you off, she may simply be saying she likes the Beatles, and you’re the Stones. No shame there. The Stones flippin’ rock!

How To Ask For a Second Date

Are there any differences in how you ask for a second date by text, as opposed to in-person?

—Cody, 33, Biloxi, Miss.

how to ask for a second date

In person, you want to let your emotions inform the words you use to ask her out. With texting, you can craft the precise, flirty message you want to send.

Here are five text messages you can send after a date, ranging funny to sincere to cheeky. Each one lets you ask for a second date with charm.

  • “Last night was great. We should do it again. Do you have a Yelp page where I can leave you a review?”
  • “Did you have fun last night? Text 1 for yes, 2 for HELL yes, 3 for ‘let’s go again’ ”
  • “I think we both agree that this needs to happen again, right?”
  • “I had this CRAZY dream last night that I met a cool, awesome, sexy woman who [insert something memorable they said or did]. Date 2 next week?”
  • “Hey, I just wanted to let you know that you had a really good time last night, and you’d like to see me again.”

Want some tips on how to get more swipes on Tinder or what to say when asking a girl out? 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 has been called one of the best dating coaches in the world. He's appeared on talk shows such as Access Hollywood and The Today Show. He's also been published in magazines such as O Magazine, Maxim, Cosmopolitan, and more. Connell helps men get out of the friend zone and find the women of their dreams. 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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