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5 Questions To Ask On A Second Date

Dating coach Connell Barrett gives you questions to ask on a second date, shares the classy way to end things, and how to play it after sex.

QUESTIONS TO ASK ON A SECOND DATE

Connell, my first dates go well, but then I lose momentum. I really want a girlfriend, but I can’t get past date no. 2. The conversations lag. Any tips on questions to ask on a second date that will help me out?

—Andrew, 33, Knoxville, Tenn. 

I once had an incredible first date with a smart, sexy woman named Kara. It was flirty, fun, and it ended with a passionate kiss straight from a rom-com. 

Our second date had a similar vibe, which I thought was a good sign. But when I texted her to ask her out again, she basically said, “Thanks but no thanks.”

Huh? What happened? 

A second date needs go deeper than the first date. Yes, you still want to be fun and flirty. But you also want to open up, be more vulnerable and “real” with her—and help her do the same with you. 

The first date is about chemistry. The second date is about connection—learning how comfortable you are as a potential couple. 

Here are five powerful questions to ask on a second date. Be prepared to answer these questions as well. (It should be a discussion, NOT an interrogation.) 

1: “What was the most defining moment of your life”?

Your date’s answer will reveal some of the values that are most important to her. 

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

This gives her a chance to admit regrets she may have about past mistakes, giving you a window into her level of self-awareness. 

3: “What’s most important for you in a relationship?”

Is it honesty? Kindness? Adventure? Her answer is basically telling you, “Here’s what I want.” You’ll want to know this, and she’ll want you to know it. 

4: “If you could change anything about yourself, what would it be?”

This question gives you both the chance to be vulnerable about your flaws, as well as daydream about the people you’re both trying to become.  

5: “What would you like to ask me?”

This question blows women’s minds, because you’re basically saying, “I’m an open book. Turn to whatever page you want.” Simply asking the question will tingle her pleasure center because this level of vulnerability is rare in men. 

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THIS IS THE END, BEAUTIFUL FRIEND

What’s your advice for how to end things when it’s just been a few dates? Do I have to do it in person? By text? Can I ghost her?

—Darnell, 25, Brooklyn, N.Y. 

Depending on how many dates you’ve had, you may be under no obligation to “officially” end it. You could merely stop asking her out. She may get the hint without you sending an “I’m not feeling it” message. It’s not ghosting unless you outright ignore her messages, which I do NOT endorse. 

Draw a line in the dating sands at three dates. You can go up to three dates and feel no pressure to proactively tell her that it’s over. You don’t need to explicitly break it off unless you’re prompted.

When should you make it clear that you’re ending things? When you’ve had four or more dates, when you’ve had sex, and/or when she keeps reaching out to see you again. After four-plus dates or after being intimate, it’s likely that one or both of you have developed deeper feelings. At this point, the right, respectful thing to do is call it quits if you see no long-term future for the two of you. 

If you decide to tell her it’s over, be honest, kind, and empathetic. Close the door, but gently. Frame it as a chemistry issue, rather than there being anything wrong with her. It hurts to hear, “You’re not enough.” It feels less personal to chalk it up to incompatibility. The message is, “It’s not you, it’s not me—it’s us.” 

When you end it, compliment her. A spoonful of sugar helps the rejection go down. Say something like, “I’ve had a great time getting to you know you, but the romantic spark isn’t there for me. It’s chemistry. I know you’ll find someone who’s as fantastic as you.” 

THE MORNING AFTER 

I’m a divorced dad, and thanks to your online-dating advice, I’ve been dating a few amazing women. Recently, I had my first-ever hook-up on a first date! (I was married young and barely dated in my 20s.) A gentleman doesn’t kiss and tell, but it was incredible. But I wasn’t sure how to act “the morning after.” Do you play it cool? 

—Leo, 42, Atlanta 

Hey, if a woman hits the Egyptian cotton with you, help her feel great about her decision. Be sweet. Spoon and pillow-talk, if she likes that. Offer her breakfast and coffee. Either drive her home or order her a ride-share car.

After you part ways, text her something lovey-dovey later in the day. Here are some texts to consider. Adjust as you see fit and add all the heart-eye emojis that you want. 

  • “My bed smells like you. This is a good thing.” 
  • “You were amazing last night, and you’re making it VERY hard to concentrate on work.” 
  • “This is my casual, chill way of saying that I had so much fun with you and I’d love to see you again.” 
  • “I can’t stop thinking about you and the way you [fill in the blank]. Just wanted you to know.”
  • “I’ve never been SO glad to be SO tired. #TotallyWorthIt”

Need more dating advice? Read What To Do On A Second Date To Spark Chemistry here.


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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NYC Dating Coach Connell Barrett

106 W 32nd St, New York, NY 10001

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