How to Attract the Man of Your Dreams/shoud I flirt?

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Question
Dear Dennis
I am an attractive and confident woman.  I have dated many handsome and rich men, but I have not found myself emotionally attracted to any of them. But recently I met this guy. His appearance is totally average. Nevertheless, he has something draws my attention. He is humble, big hearted and very dedicated to what he does. And I just love the way he talks and treats other people.  I think I am having a crush on him. It is an amazing feeling. I have not had this kind of feeling since I left high school 10 years ago.
Now, the question is, how to let him know that I am actually interested in him. I am cheeky and flirty.  But this man is different. He is funny but he is not cheeky type of guy.  He always treats me with great respect.  If I flirt with him, he might be disturbed.  
Second problem is, I have been sending signals that I am happily being single – I did this to avoid being asked out by guys around me and guys that I need to work with on a regular basis. I think he might have picked up that signals too. What I should do now?
Most importantly, I have fears of hurting him. If we break up one day, it will be an embarrassment to both of us, especially to him.  
I know I am playing cool. But the fact is I am very into him. I know he is the guy that I can love and trust. I have feelings that I will find true peace and happiness if I am with him. I can not stop thinking about him. Please help me with the above three questions. 1, how to let him know I am really keen on him. ( I am friendly person and I like everyone, but I need him to know that my feeling for him is special) 2, he knows I dated rich guys and handsome guys before… will he feel uncomfortable about this and will he reject me because of this? 3, should I or shouldn’t I have fears of hurting him? If we date then break up, will it bring tension to us and our friends?
I look forward to having your advice.
Nina  

Answer
Hello Nina!

No, you're not playing cool - you're playing cold - maybe even frozen! I have to say, you sure put a lot of power into your own hands here. You want to be responsible for everything from guys interest in you to their careers and possible embarrassment! Frankly, that makes you come off as pretty damn arrogant.

Let me get to your questions:

1) You tell him, but you tell him intelligently. Instead of just saying, "Hey! I like you!" say to him, "You know, I'd be interested in getting to know you a little better - maybe over a drink one night?" Here, you're not asking him out specifically, but you're opening the door in order for him to make the next move. If he's interested, he's very likely to do so.

2) I don't know him and I don't read minds, so I can't say.

3) What the hell business is it of yours whether he hurts or not? That's his choice - not yours! You should be worried about whether he breaks YOUR heart, not the other way around.

Unless....

You plan on staying stone-cold and trying to lead him on where you don't invest yourself at all and he has to do all the giving. This again isn't so much about him however as it is about you.

What I sense here Nina isn't that you're really so cocky-confident that you're really not interested in guys; it's that you're very insecure and terrified if being hurt. Thus, you're only looking for the situation where that can't happen. Let's face it, if you don't invest yourself emotionally in someone else, it's not going to happen. Of course, you'll simply remain alone the rest of your life too and that's not a very lofty goal in my opinion; although it is pretty safe.

Dating, sex and relationships are situations where the benefits you recieve are directly related to the risks you take. There is no such thing as a "healthy relationship" where both people aren't equally invested emotionally and thus, share the risks of being hurt.

Frankly, I'd want more for you, but it's not up to me - YOU have to want more for yourself.

Best regards...

Dr. Dennis W. Neder
President
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Remington Publications
818.334.8826
http://beingaman.com
Publishers of "Being a Man in a Woman's World I & II"

How to Attract the Man of Your Dreams

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Dr. Dennis W. Neder

Expertise

Literally, any question related to finding and meeting the man of your dreams. I am the top-rated expert in "General Dating Questions", "How to Attract the Man/Woman of your Dreams" and "Places to Meet People". In fact, over the past few years, I've answered over 32,000 letters from readers, have written over 700 articles, written numerous books, recorded CD's and DVD's, done hundreds of radio and tv shows and have millions of readers all over the world. If your question is particularly sensitive you can also write to me privately and securely at: dwneder@beingaman.com.

Experience

I've written many books on every aspect of dating, sex and relationships. My new book, "How Women Can Approach Men" is already quickly becoming one of our best-sellers! Women have many tools at their disposal and shouldn't have to wait for "Mr. Right" to come along! After reading some of the advice the women in this section are getting from other women, I think it's a good idea to offer a man's perspective.

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Numerous boards and commissions, civic organizations, etc.

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Thousands of websites, magazines, radio and TV.

Education/Credentials
Doctor of Philosophy

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