5 Questions to Never Ask a Woman on a First Date.

via instagram @wineandshine


In my 25 years of being a relationship expert and personal matchmaker, I found that women love to be with men who inquire and ask meaningful questions. They demonstrate that you are interested in her as a person, able to focus your attention, and can sustain a conversation. However, asking the wrong questions can kill a date no matter how well it’s going. Here are 5 questions to never ask on a date and what to ask instead.

Book Your 90-Minute Relationship Coaching Session with Level Connections Founder, April Beyer

Why Are You Still Single?

You meet a woman who seems confident, smart, and beautiful. How is it possible that she’s still single? Before you know it, the question comes flying out before you notice the look of shock on her face.

What to do instead:

Some of the most incredible women are selective and not in a rush to marry the wrong man. Don’t rush to judgment. Be happy she’s still available!  Ask about her previous most meaningful relationship and what attracted her to him. If you’re listening, you’ll hear why it didn’t work and get a sense of her ability to choose good or bad guys.

Where would you like to go for dinner?

Every woman wants a man with a plan. New women in your life can’t gauge your income level or what’s comfortable for you in choosing a location. Even if you’re being nice, asking the question makes you look like you’re not in charge and that will backfire later.

What to ask instead:

“I’d love to take you to one of my favorite restaurants near your office/home. How about Friday at 7 pm?” If she has any dietary restrictions, she’ll let you know.  It’s not about the restaurant, it’s about the company!

Want to come back to my place?

Slow your roll. I don’t care how hot the chemistry is, don’t ask a woman back to your place (or hers) on a first date. It makes you look like you only want one thing and gives the appearance that you’re desperate in a hurry.

Would you like to go out again? (during your first date)

If you’ve ever wondered why a woman said yes to a second date on a first only to later ghost or change her mind, it’s directly tied to WHEN you asked her. The worst thing you can do is ask a woman out mid-date. She’s a captive audience and will say yes just to not be uncomfortable mid-date.

What to say instead:

“I had a great time tonight. I’ll give you a call soon so we can get together again. Can you text me when you get home so I know you arrived safely?” (Brownie points!)

How many bad dates have you had on the dating apps?

Every day, all over the world you can hear the constant echo of singles complaining about the last ridiculous and painful dates they’ve been out on. It’s common and it’s nothing more than a crutch when you can’t think of anything else to say or ask. Don’t do it. Even if the person you’re with is lamenting about her past blind dates, don’t engage.

Instead, ask/say:

“Tell me what you’ve enjoyed the most about dating.”

By being more thoughtful about your questions you’ve just opened the door for some great connection and started out on a positive instead of a negative.  Not to mention, you’re going to stand out in a sea of other guys trying to get her attention. Date smart and you won’t go wrong.

Questions are the key to inciting chemistry and figuring out if your values align.  LEVEL asks these questions before you go on your first date so conversation should be easy.  We already know you share the same values!

“In my 25 years of experience working with single men and women, I’ve found successful relationships are built on a solid foundation of self-knowledge, clarity, and confidence. With my private relationship coaching, you can embark on a transformative journey that will lead you to a deeper understanding of your core values and align you for successfully developing a truly fulfilling relationship that can last a lifetime.”
– April Beyer, Founder & CEO of LevelConnections.com

Leave a Reply

Your email address will not be published. Required fields are marked *

You’ve got options, we’re here to help you choose the right one.