Dating Dilemmas of Successful Women: Should You Ask Him Out and Plan Dates?

ask him out

Should you ask him out and plan dates?

As a smart, successful woman, it can also feel natural for you to take the lead. After all, you do so in many other areas of your life. After a job interview, you follow up the next day with a thank you note listing all the reasons you’re qualified. And when you don’t hear back, you send another email. So, if you meet a guy and like him, should you ask him out on a date?

Have you ever found yourself going into overdrive trying to “make” a relationship move forward? This can be oh-so-tempting when you like a guy. You want to make sure he’s getting the memo that you’re interested, so you might go out of your way to ask him out, plan dates, initiate phone calls and texts, maybe even bake him his favorite cookies.

Dating is its own kind of dance.

In the beginning, it’s best to lay back and let the guy take the lead in planning.
As I mentioned in my blog post on Accessing Your Irresistible Feminine Power, men thrive on being the ones who do things for you. They love women who are receptive to their pursuit, their suggestions and ideas. It brings out the best in them. And you’ll be surprised by how much you enjoy it too!

What’s more, you want a guy who goes out of his way for you. Someone who is crazy about you!! Letting him take the lead allows his interest to come forward and shine. And you get to assess whether he is right for you.

So, in the early stages, it’s best to sit back and let him do the work. Only pick up the ball in the process of fleshing out something you have both agreed to do. For example, if he asks you out to dinner and wants to know what you’re in the mood for, tell him what you like. Or if he suggests you get together and has trouble planning a date or offers two options for activities, let him know your preference. But for the most part, stay open-minded and let him impress you, even if it doesn’t quite hit the mark.

Over time after a few dates, you can begin to suggest activities like asking him out, as the friendship that underlies great love begins to flourish. By that time you will know that this is a guy who is truly into you!


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Dr. Diana Kirschner

Diana Kirschner, Ph.D. is a relationship advice expert, frequent guest psychologist on The Today Show and the creator of a globally available dating coach and Love Mentor® program. Dr. Diana is also the best-selling author of the acclaimed best-selling relationship and dating book, “Love in 90 Days”. Love in 90 Days was the basis of her PBS Special on love. Connect with Dr. Diana through her Dating Tips & Relationship Advice Newsletter.

“Diana Kirschner’s work is life-changing, love-affirming and wonderfully effective.”
~Dr. Christiane Northrup, Internationally bestselling author of Women’s Bodies, Women’s Wisdom.


  1. Jason on December 4, 2016 at 5:00 am

    Hi Diana,
    Congratulation on this short, sweet post. This is really awesome.
    I love the idea that girls should let the man ask first. But asking someone out is really terrifying, so the man is probably only going to do it if he’s absolutely, positively, beyond a doubt sure that there’s a good chance of her say yes. Otherwise he may chicken out. This is why it’s essential that the girl make it pretty clear to the guy she’s flirting with that she’s receptive to the idea of his asking for her number or inviting her to hang out.
    Great share, and thanks for the good tips.
    I’ll be sharing with my friends. 🙂

  2. Gustavo Woltmann on January 12, 2017 at 8:59 am

    For me, there is nothing wrong if a girl ask for a date. It will make me feel happy that someone likes me.

    – gustavo woltmann

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