5 Biggest Mistakes Women (Unconsciously) Make That Keep Them Single

You can set yourself up for failure from the very first date.

Last updated on Oct 13, 2023

Awkward date Liza Summer | Pexels / Africa images | Canva

By David Wygant

I got a great email the other day from a woman who was writing just to brag about how amazing she is, but had one question: "Why am I single?"

Actually, she said she was writing to ask me why can’t ever get a boyfriend. Her email, however, was entirely about how great she is. She told me that she was successful. She’s sexy. She can run her own business. She’s running her own department.


Don’t get me wrong. I’m thrilled that this woman feels so confident about herself. The problem for a lot of women like this is that they take their business side with them when they go out on first dates. They act like interrogators when they're on a date. They don’t flirt. They sit there and basically conduct a date like a business interview, asking the guy questions and putting him on the spot.

RELATED: 14 First Date Do's And Don'ts Guaranteed To Score You A Second Date


Here are the 5 biggest mistakes women unconsciously make that keep them single:

1. Conducting your date like a business interview

When a woman is not very flirtatious, the guy will leave that dating feeling like he’s just been on a job interview. He will be wondering why this woman interrogated him for two hours. He will be wondering why, on the first date, she asked him whether he wants to have kids and how many kids he wants to have.

I have seen women do this over and over again. They think that they are weeding out the wrong guys by asking all these questions on a first date. In reality, though, they are conducting a business interview. A date is not a business interview. A date is a way for you to get flirtatious, have fun, and be sexy and playful.

All these questions you’re firing at the guy, you will find out anyway. Within the first month, you are going to find out about all this stuff you seem too anxious to know on date number one. You don’t need to drill someone about them on the first date.

2. Competing with the guy

So many women who compete with men in the business world take that same personality and compete with men on dates. I know that when I was single, I never cared if a woman made more money than I did as long as she didn’t act like an interrogator on our date.


As a man, I don’t need to be the breadwinner. I just want to feel wanted and desired — sexually and emotionally. The problem is that a lot of these women don’t allow a man to feel that on a date. They are adversarial.

RELATED: Researchers Identified The Tactics Women Use To Flirt Competitively Against Other Women, But Do They Work?

3. Forgetting to flirt

You need to flirt on a date. Period.

What do I mean by flirting? You need to look into a guy’s eyes, smile, compliment him, and laugh when he says something funny. When you don’t do these things, you’re just in business mode. This is what so many women do. They stay in business mode instead of being in flirtatious, fun mode.


4. Not touching him

Another thing that a lot of women fail to do on a first date is touch. No, I don’t mean to grope a guy or touch him in any kind of overtly sexual way. Not touching a guy at all, though, is a mistake.

Touch his hands or his shoulder as you walk. If you don’t touch a guy at all, then you’re not showing any form of sexual communication. Touching a guy in this way is just a nice, subtle way to show the guy that you’re interested.

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5. Not dropping any hints

Would you like to get together again? You need to drop some hints. Men love little hints.


Say you’re talking over dinner and he mentions his favorite band (which happens to be a favorite band of yours as well). Instead of just saying that you love that band’s music, say something like “I think they’re coming here in concert soon.” By saying that, the guy will be likely to say something like, “If they’re playing here soon, then you and I are going.”

It’s a little bit like fishing. If you drop the bait, the man will take it. You have to drop the hint so the man asks you out again.

If this sounds like you — if you’re a successful woman who goes out on a lot of first dates and almost no second dates — then you need to really rethink the way you are conducting yourself.


You’re getting dates. That’s half the battle. The other half is how you conduct yourself on those dates. That might be the real battle for you.

RELATED: How To Get A Man To Make A True Commitment

David Wygant is a dating coach who spent the past 20 years helping men and women transform their love lives. As a lead writer for Ask Men and Huffington Post, his advice has been featured on television, newspapers, and magazines, including MTV, The New York Times, MSNBC, Fox News, Cosmopolitan, Men's Health, E! Entertainment Television, and more.