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!

find mr. right this year
  • This field is for validation purposes and should be left unchanged.

Sign up here for a powerful gift!

BREAKTHROUGH-to-LOVE Premium Coaching Session!

Limited time offer- Free



Tired of loneliness and disappointment in your love life or marriage? This will change everything...

As a relationship expert, I've helped thousands of women get the love they want-even when it seemed impossible.  I'm Dr. Diana Kirschner. You might know me from my PBS Special, seen me on Oprah, or have read one of my bestselling books.

I want to do everything I can to give you hands-on personalized support that will make a lasting difference.

That's why I'm excited to offer a FREE 40 minute Breakthrough-to-Love-Coaching Session via Skype, Zoom or phone.

During your powerful and dynamic one-on-one session, we will help you with your unique relationship or dating situation. You'll walk away inspired, with a clear step-by-step path forward to move through any obstacles and get the love you want.

Here's what women like you are saying:

"My session was an incredible game-changer! I was finally able to see a way forward with my boyfriend and he has proposed!

I'm very grateful!" -Jenn in New Mexico

matchmaker, dating coach, dating tips, dating & relationship advice"I was fifty-two years old with a career that was enviably successful. But my love life was not. And I couldn't figure out why. As my love mentor, Diana helped me understand that I not only deserved to have but could have a strong, loving life partner who would always be there for me.  I found true love in three months! And after 4 plus years of marriage, my husband and I still pinch ourselves every day to make sure that it's not a dream!" - Midge Woolsey


  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

Leave a Comment