Kavita looking silly on the beach

Are you afraid to look stupid with men?

Today I want to tell you a story about my client Kelsey.

Kelsey is a powerful woman who works to raise millions of dollars for nonprofits. If you were to meet her on the street she would have the kind of outfit you would love to have put together. When she speaks she is eloquent and you immediately know how smart she is.

Overall, she definitely has her life together.

Kelsey was introduced to a guy through a friend, and they are long distance (she lives in NYC and he lives in Austin). When she was visiting Texas a couple of months ago to see her mom, they decided to meet and have dinner. They had a great time and he asked when she would be back. She said probably in May.

So, this past month when she went back, Kelsey was even more excited to go on a second date with Ben. She wanted to get to know him better by asking questions and revealing more of who she was. More than anything, she just wanted to feel comfortable being herself.

As soon as we got on the phone for our last session, she launched into how embarrassed she was and that there were multiple times on the date she felt really stupid.

At the beginning of the date he asked her to put a collar straightener into the collar of his shirt and she didn’t know how to do it.

During dinner they were talking about social media and Ben said he doesn’t really like being on Facebook because it can be distracting. Kelsey responded with, “Yeah me neither” meanwhile she had been “stalking” him on Facebook for several months since their last date.

At the end of the date when she wanted to say something flirty what came out was, “Thanks for the intellectual stimulation.”

That last one was where I started laughing. Knowing who she was, it was hilarious what came out of her mouth out of nervousness at the end of the date!

Kelsey said to me, “I know it is funny! But I felt so stupid. What do I do now? I feel like I totally embarrassed myself . I just wanted to be myself and this is how I reacted.”

I said to Kelsey immediately, “You didn’t do ANYTHING to screw this up. I actually think the fact that you felt stupid several times during the date was REALLY good. Often you can look so put together that men feel like ‘Why would this woman need me?. She’s perfect. She’s got it together.’ The fact that you were flustered and embarrassed at times was so good.”

Being willing to look stupid shows your humanness and realness. It softens you.

I explained to Kelsey that the more she can feel stupid in life the better, because it is an indication of her getting outside of her comfort zone. It is a way for her to let go of control (which I know we all love) and let her guard down and let someone see who she really is, which is a smart, loving, flawed human being.

On this date, Kelsey actually revealed parts of herself in a more spontaneous way than she ever had.

Have you ever watched a speech that someone gives, whether it be at a wedding or something formal?

The speeches that touch your heart and move you are the ones that show someone’s humanness, imperfections, goofyness, and honesty.

In those moments they are risking looking stupid (not looking perfect) and that is what moves people.

It is the same on dates. The more you let yourself make mistakes and look stupid, the better. When you are with the right man he will see that as the most endearing quality you have.

Kelsey and Ben are still talking and he is looking forward to seeing her soon.

This week, Your Lovework is to share in the comments below a moment you felt stupid on a date or with a man you just met. How did you handle it? I want to hear.

In Love,


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