This Is Why Men Shouldn’t Be Afraid To Take The Lead With ‘Intimidating,’ Successful Women

Take the lead.

Let me explain how I unwittingly fumbled onto this.

Many moons ago, I went to dinner with a CEO of a tech company in San Francisco. Not going to lie, I was a little intimidated and not sure how to handle the situation. I mean, she’s a boss—should I take the lead by planning the date, making the decisions and taking care of her—or would she rather be in control of the evening?  What do you want to do?  Where would you like to go?

I took the lead. Planned the date. It was supposed to be just dinner at a nice restaurant in her neighborhood, but when we had great conversation and chemistry (let’s call these “special feelings”), I took her hand, grabbed a cab, and took her to a bar atop one of the city’s oldest hotels with a panoramic 360 view. Once there, I gently dragged her onto the dance floor, and not long thereafter kissed her for the first time. And thus, we started dating.

I must admit, it was a strong move, especially for me, a “nice guy.”  Looking back, I probably let women lead most of the time on dates. But you know what this lady later told me?  She loved it. In fact, she had never gone on such a date, it was “not like her” to continue a first date dinner with drinks, and certainly not with a kiss.

She’s a boss, usually in control. Men don’t do that with her—take the lead.

She makes the big, stressful decisions all day as the boss, she loved being able to sit back and enjoy herself as I took care of everything.

That was unexpected, as I thought power women would prefer to be in charge on a date. Maybe it was just her. Then it happened again—I took the lead with a successful woman, and she loved it. And I started to ask women what they want, you know, in a man and relationship. And what they are most attracted to. I thought they would say the typical “asshole alpha” type man. But often, women said a “strong masculine man that can take the lead.”

Am I beating a dead horse, here, fellas?  I think my thesis statement is clear. Try this, and see if it works for you.

Especially if you are a “nice guy” or are not having the success on dates you want, consider taking the lead.

Now if you are already doing this, or are a bit of a manly/strong man already (I did not say asshole jerk), you may want to calibrate things by checking into your lady’s body language and facial expressions, or just flat out asking her if she is having a good time.

Here’s how to do it.

1. Get to know her.

Any food restrictions? Top 3 favorite kinds of food to eat? Give me three after-date activities you like (not Netflix, dudes. We need to elevate that game). More of a dive bar/karaoke queen, or live music or art show?

2. From what you know she’s into, plan a date that excites you and is something you want to do.

Start with dinner/drinks, and have a couple options for afterwards that you can lead to if things are going well for both of you (see special feelings above).

3. Take care of her on the date.

Pick her up at her place. Open her doors, pull her chair. When the time is right, hold her hand. If some slob is repeatedly looking her up and down, make eye contact with him, tell him he’s a creep and to knock it off. Make it clear she’s with you, you are taking care of her, and she has nothing to worry about but having fun with an incredible gentleman.