I Am a Nice Guy With Little Dating Experience. How Do I Get a Woman to Go Out With Me?

Good Morning Evan,

I have a bit of a dilemma. I am almost 21 years old and I have only dated one woman in my life and I dated her for 4 years. She broke up with me in the summer of 2006. I’ve asked out several women since then, and they all rejected me. Just a few months ago I moved to Florida, and I’ve asked out two women and they both said no to me, too. I think I must be cursed. I feel scared to ask out any other women for fear of being rejected. The worst thing about this is that the last woman told me to never change who I am because I gave her a rose for New Year’s Eve. She said a man had not done that for her in a long time. But if she won’t go out with me, how can I be myself? In a way, I have an identity and a dating crisis.

I heard you were an expert, so how do I get a woman to go out with me?


Nice guys rarely do well with women, but it’s not BECAUSE they’re nice. It’s because they have no confidence.

Dear Alex,

Your crisis isn’t an identity crisis or dating crisis; it’s a confidence and perception crisis.

Your sample size of experience is so small that you’ve turned every tiny setback into a disproportionately large failure. This is impacting your perception of the world to view yourself through a prism in which you are “cursed”, “scared”, “rejected” and afraid all in one paragraph.

Ready for Lasting Love?
Ready for Lasting Love?

So let’s shake you out of this funk and set your record straight.

(This goes for any other reader – male or female – who has ever felt a lack of confidence in his/her ability to date. Dating failures are almost ALWAYS perception and confidence problems and not real problems.)

Okay, Alex. Your question says it all: “How do I get a woman to go out with me?”

The answer is: “You don’t. You become the man that she wants to go out with.”

It may sound like wordplay, but I assure you, it’s not. Our job as human beings is not to make anybody do anything. Every email I receive that says, “How do I make a man want to commit to me?” misses the point. You can’t make a man do anything. All you can do is be the kind of woman that makes a man never want to never leave. The focus is on who you are, not on how you want him to act.

Same for you, my rose-giving friend.

You’re a nice guy. Nice guys rarely do well with women, but it’s not BECAUSE they’re nice. It’s because they have no confidence. They don’t inspire, they ask permission. They don’t lead, they follow. They don’t trust their judgment, they want to see if their judgment is okay with their girlfriend. And they certainly don’t believe that they’re good enough to get any woman interested in them – they just feel fortunate to be in the conversation at all. In short, nice guys have to grow a set of balls.

This isn’t my opinion. This is me, as a dating coach, translating what I’ve heard from thousands of women. They don’t like bad boys BECAUSE they treat them poorly – they like them IN SPITE of it. Why? Because bad boys inspire, excite, lead and generally appear to have things all under control.

Seriously, bro, you’ve asked out TWO women in Florida who weren’t interested – and now you’re afraid you’re cursed?

Women want to be equals with men; they don’t want to be able to control us. The second they can control you, Alex, they’ve lost all respect for you.

I’m guessing that you’re sending out a pretty strong signal to women that they can control you. This is something that feeds on itself and has led you to this crisis of confidence. Seriously, bro, you’ve asked out TWO women in Florida who weren’t interested – and now you’re afraid you’re cursed?

By extension, a baseball player who hasn’t gotten a hit in his first two at-bats must fear he’ll never get a hit again. An oncologist who has lost two patients to cancer must consider hanging up his scrubs. And someone who is unemployed and sent out two resumes without a response should pretty much resign himself to a lifetime of unemployment.

This is what I mean by your lack of perspective.

I’m not making fun of you – not at all! I’m a guy who had to ask out three people before he got a prom date; a guy who didn’t lose his virginity until his sophomore year in college; a guy who didn’t have a relationship over a year until he got married. This stuff doesn’t come naturally to lots of folks, which is precisely why I still have a job. And I am living proof that you can learn – with considerable practice – how to understand the opposite sex. Your problem is that you are more focused on having the opposite sex understand you.


This is very common (especially for women, who should reread that last sentence.)

Instead of hoping that the opposite sex suddenly starts appreciating you, your focus should be on understanding what the opposite sex finds attractive and making small steps to becoming that person.

A nice guy can still be nice and do well with women.

A strong woman can still be strong and do well with men.

But something fundamentally has to change in your attitude, Alex, in order to make a breakthrough.

For the sake of brevity, I’d recommend three things:

1) Drop the idea that you’re a failure. Nobody wants to buy a car from a salesman who doesn’t believe in his own product. Your insecurity and negativity and fear is all over you.

2) Find a few guy friends who are good with women. Hang around them. Take mental notes. I remember the first time I did this and realized that my friend – the rush chair of his fraternity – was so great with girls simply because he didn’t hit on any of them. He was like the mayor of the party – getting everyone drinks, dancing with everyone, making everyone laugh. He was so NOT concerned with what anyone thought because it was HIS place; he could do no wrong. Make the world your place, Alex, and women are going to want to hang out there.

3) Get used to failure. Thomas Edison tried 10,000 different ways before inventing the light bulb. Maybe he should have just stopped at 2 because he was “cursed”. Every successful person has failed at something. Most of us have failed a lot more than that.

And if you’re reading this and saying to yourself, “This makes sense, but HOW do I make these changes to develop more confidence and perspective?”, click here to learn more about my coaching. You’re probably a lot closer to success than you even realize. You just need a little push.

Good luck.