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14 Deep Questions To Ask a Girl

Dating coach Connell Barrett provides deep questions to ask a girl, the secret to motivation, and the easy way to flirt with charm.

Deep Questions To Ask a Girl

I know I need to keep things light when getting to know a woman, but I also love having deeper, stimulating conversations. Is it OK to “go deep” and talk about real stuff? What are some deep questions to ask a girl?

—Carter, 40, Auburn Hills, Mich.

Early on in a recent relationship—two or three dates in—Brianna and I were sitting on her couch playing Scrabble when she asked me if I’d ever cheated on any of my exes.

“Yes,” I said. “More than I care to admit.”

Her reaction? Understandable shock at my infidelity, but she also felt something bordering on excitement. I was being so bracingly candid with her, and that part she liked.

I went on to tell her why I had been unfaithful, and how I had learned from it—and, of course, had mended my ways. (I used to be a mind-bogglingly self-interested person.) The talk brought us closer together.

Now, I’m not saying that on date no. 2, you should admit all your past sins. I just want to underscore the power of “going there” and having a deep conversation.

Yes, Carter, the overall vibe of your interactions in the courtship phase of dating should be light and fun. But you can—and should—burrow below the surface.

Real talk can create real connection. The right questions can help you both become more vulnerable and emotionally naked.

Here are 14 deep questions to ask a girl. (Heads up! Always be prepared to answer any question that you ask. And “deep” does NOT mean “depressing.” (Keep things positive!)

1: “What was the best day of your life?”

This summons good vibes, gets you both swapping stories, and makes you share a sense of gratitude. (I LOVE talking about my dad’s surprise 85th birthday party, which I planned with my three sisters… and which my ailing mom was able to witness not long before she passed. Best. Day. Ever.)

2: Who is your hero?

Whether it’s her dad, a former college professor, or Harriet Tubman, her answer to this question will give you a deep insight into who she admires as well as who she is at her authentic core.

3: What’s the most courageous thing you’ve ever done?

This question lets you take turns talking about being the hero in the story of your life.

4: If you could go back in time and give your younger self some advice, what would it be?

A fun time-travel thought experiment that lets you admit regret and share life lessons.

5: What’s your biggest flaw?

Don’t give the bullshit, job-interview answer here. (“I care too much.”) Keep it real, yo! It takes confidence to admit flaws, and women love confident men.

6. What do you love most about your job/career?

This question lets you both talk about work in a positive, emotionally evocative way, rather than boringly asking her, “What do you do?” And you can follow up with, “Why do you love that so much?” This helps her dig deeper.

7. What’s your hidden talent?

Can she do cartwheels? Rock the karaoke mic? Recite all the state capitals? This question allows her to show off a bit while also revealing a secret—and sharing small secrets builds trust on first dates.

8. What’s your dream travel destination?

Hey, everyone likes talking travel. It’s aspirational, and the two of you might find out you’re both just dying to see Machu Picchu, or run with the bulls in Pamplona.

9: Who would you want to play you in the movie of your life?

This question caters to your date’s ego—and the actor that she chooses will clue you in on how she sees herself.

10: Who did you see for your first concert? 

Music is a great first-date topic. Prepare to be impressed when she mentions Beyoncé, or playfully tease her when she admits that it was Nickelback.

11: What’s a favorite memory from childhood? 

A first date once told a great story from grade-school, about the time she got dressed up as a clown for Halloween and went to school… on the wrong day! All the other kids were dressed normally, while she sat there in her red wig and clown makeup. Sharing stories from childhood offers your date a chance to be vulnerable or tell funny stories. Also, teeing your date up to tell a story lets them shine, and take center stage.

12: What do you love to do for fun?

We all love to talk about our passions and hobbies, so this question is likely to kick-start a stimulating conversation. To take it up a notch, add some cheeky confidence by saying this, with a sly grin: “What do you love to do for fun—besides go on first dates with charming, attractive men like me?”

13: Who was your first kiss?

Everyone remembers their first kiss. This question takes things in a romantic direction, but also keeps the vibe innocent. But you can spice things up by asking…

14: What’s the craziest place you’ve hooked up?

If things are going well and you’re both opening up, feel free to ask this riskier, PG-13 question, which can help spark a sexy vibe. Just be ready to answer your own question!

Now that you have a list of fun, deep questions to ask a girl. Go try them out!

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What's My Motivation?

I know I should be out trying to date, but I just don’t feel motivated. And it’s taking a toll. I’ve gained about 20 pounds during lockdown, my social skills have all but vanished, and I’m lonely. I’d love to find a wonderful girlfriend, but I can’t get excited about dating. Can you give me some motivation?

—Gabriel, Portland, Ore.

couple outdoors - deep questions to ask a girl

At the end of “The Wizard Of Oz,” the Scarecrow, Lion and Tin-Man all learn that what they wanted—brains, courage, heart—was within them all along.

Motivation works the same way. No one can give it to you. You have to summon it from inside.

Here’s a great way to do that. Give yourself a clear, compelling, specific vision for your dating life that gets you excited and juiced.

I call this your Amazing Dating Outcome. When you lack this vivid vision, you lack direction and motivation, leading to loneliness and, in your case, low confidence and even weight gain.

This is the problem with New Year’s resolutions, which have an 80 percent failure rate. (Most people quit by mid-February.) You feel PUSHED by sheer willpower. But you need to be PULLED by excitement to achieve a great goal.

When you know exactly what your outcome is, even when you get off-track, you know your destination and can correct course. When a jet takes off from JFK for a coast-to-coast flight, it strays from its intended flight path much of the time, as the pilot adjusts for turbulence and other planes. But it lands at LAX right on the white stripe.

Your Amazing Dating Outcome should have three elements.

1: It’s amazing to YOU. It excites and juices you.

2: It’s measurable (examples: “two dates weekly”; “get a sweet girlfriend I love by the holidays”).

3: It’s an outcome—a place of arrival.

To turbocharge your Amazing Dating Outcome, know your WHY—the deeper reasons you want to achieve it. What will your outcome let you feel or give? How will you grow?

A strong WHY gets you in touch with your deeper purpose, fueling you to massive action. (At the same time, understand that life-changing results will take time. Your love life is like an ocean liner—there’s a lag between turning the captain’s wheel and changing course.)

Here’s an example of an Amazing Outcome from my client Brad: “To overcome approach anxiety so that I can meet women at night in the bars and also in the daytime. I would like to date around for a while and then choose a great girlfriend based on who I connect with the most. I would like to be in a relationship in six months or less.”

His WHY: “It’s about feeling more confident and attractive, knowing I didn’t settle. Also, I love being a boyfriend and having that companionship.”

Flirty Deeds

I’m single again, and I’m trying to flirt with women I talk to in my local coffee shop, but it’s not going well. I went up to one woman and said, “You are the most beautiful creature I’ve ever seen.” It didn’t work. Got any flirting advice?

—Chaz, 36, Atlanta, Ga.

deep questions to ask a girl. How to flirt

Don’t call a woman a creature—unless you meet in a black lagoon and she has gills.

Here’s the thing: There’s a fine line between flirting and fawning, and it sounds like you’ve been fawning over women, not flirting with them.

An easy mistake to make is fawning—being too impressed by a woman too quickly. Such comments might include, “You are just so amazing,” “I’ve never met anyone like you,” and “Wow, you are so beautiful!” Those things are fine to say after the two of you have made a genuine connection.

But if you lay it on too thick too soon, you can come across as her groupie, not her equal. That’s a big turn-off because  it makes you seem “beneath” her. And no one wants to date beneath themselves.

So don’t fawn. Flirt. I define flirting as showing a woman that she’s affecting you but in a casual, no-big-deal way. This makes her feel sexy and attractive, without putting her on a pedestal.

Here are examples of being affected by her but not fawning over her.

  • “Sorry, what did you say? Your lips were distracting me.”
  • “That dress is very . . . wow. Anyway . . .”
  • [On a date, after she says something you approve of] “That makes me want to make out with you, but I’ll try to behave myself.”

To see a master flirt in action, watch clips of comedian Craig Ferguson on his old CBS talk show, “The Late Late Show.” Whenever a beautiful starlet was his guest, he always let his attraction show with humor and class, and he never fawned.

Want some tips on what to say when asking a girl out or where to go on a first date? 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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