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Dear Gay Best Friend,

I have a dilemma and I need your advice. I’m a 29-year old successful, educated, well-rounded (you know, the credentials of every great woman), yet I am still single. Why?!? I don’t know.

Lately, I have been meeting men only to have a few conversations on the phone but no dates. Some friends of mine tell me that there is nothing wrong with asking a man out on a date and that I should be more aggressive. Others state that I should not ask men out and let them ask me first. Personally, I’m a firm believer that if a man wants to spend time with you he will ask you out regardless. It should not be a game. Why should I have to ask first?  That’d not my line. He is the man; I am the woman. I know my position. Am I right?!?!

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So I put this “women asking men out” theory to a test… is my story.

I recently met a guy at a party. It was obvious we were attracted to one another so we exchanged numbers. We talked on the phone to get to know each other and the conversations were nice, but weeks would go by and still no actual date. At this point I would have stopped talking to him, but I figure let me try this “theory” out to see what the outcome would be.

During one of our many conversations on the phone, I asked him when he is available to hangout. His response, “I have a flexible schedule just let me know when your available.”

Now, at that very moment, I am thinking, okay maybe this theory does work after all.

Then, two days later go by, I text him that I have an opening and we should meet up for dinner and drinks at a chill spot. He texted back, “sounds good.” I texted back with the day and place. He never replies back.

Now, I know he got my text message and he was open once he texted me back with a “sounds good.”

Days have gone by and I haven’t heard from him since. I took his number out my phone because obvious something went hellah wrong. Maybe I overstepped my position as the woman? Maybe he was not interested in the first place? Could he already be involved?  Was I not aggressive enough?  What the hell happen?!?!?!

So my question to you, Terrance, and the Hello Beautiful readers: Should women ask men out or initiate a first date? Please give me the hardcore advice/truth. It will set me free. – Hopeless Dater

Dear Ms. Hopeless Dater,

Well, he’s not the one for you. And, I wouldn’t put too much energy or focus into it. But, Ms. Honey, I will say this: You tried your theory on ONE guy and now you’re making an assumption that ALL men don’t like women asking them out.

And, it just goes to show you, and what I know to be true, that when you are committed to a “story,” or an “idea/thought,” the universe will provide you with the very experience to make your “story,” and “idea/thought” the very reality that you believe to be true.

The ONE man you found attractive, and had some conversations with, and then after several weeks and he had not asked you out, you decide to ask him. But, with that little bit of doubt in the back of your mind, that hesitancy, and reluctance, you figured you’d ask him and see if the theory of asking a man out isn’t such a big deal. And, I’m sure as you’re asking him, you’re thinking to yourself, “This isn’t going to work. This is some bull-ish. Why am I asking him out? He should be asking me. Nothing good is going to come of this.” And, lo and behold, you got what you thought, had been feeling, and continue to think. Now, you get to be right in your self-righteous thoughts that men should ask women out, and not women asking me out.

So, if you really want to date, and you really want to meet a man, and you really want to see if the theory is true, then you’ve got to test more men. You’ve got to get out of your head, out of your negative thought process, and let go of the idea that only men should ask women out. If you truly will let that idea/thought go, then I’m sure you will have a different outcome. And, if you’re wondering why you are single, then, it could be that you’re waiting on Mr. Right to come along. And, sometimes, you may have to speak up and let Mr. Right know that you are available. You may have to approach him, and get his attention. I’m just saying.

But, if you’re committed to the idea that a man should ask a woman out on a date, and that no woman should be so aggressive, or assertive with a man, then don’t worry about what your friends think. Don’t worry about what anyone thinks for that matter. Be patient, and wait on the man. Don’t lose sight of your morals and values because of what others think. If you believe wholeheartedly what you believe, then no one can fault you or make you wrong for it.

But, I am curious as to the part of your story where you say you texted him with a day and place for you two to get together, and he never replied. Sooooooo, why didn’t you call him? This boggles my mind that you were awaiting for him to respond, and when he didn’t, you immediately deleted his number from your phone because you assumed he was not interested. But, yet, you never called him to find out if he got your text. You never called him to confirm the day and place.

You see, this is why I always call folks after I send them a text confirming something if they don’t reply. Because there are times that technology does not always work, and many texts do not go through. I’ve had many friends tell me that they sent a text, but unfortunately I never got them. And, then they discover that it either didn’t go through, or they thought they sent the text but didn’t, and, sometimes my phone was acting up and days later I would get the text. Technology is not reliable, but a phone call is!

Therefore, do what makes you happy. Whatever you feel brings you joy, happiness, and the possibility of being with someone, then do it. But, keep in mind that you’re 29-years old, single, well-rounded, got it going on, but, you’re sitting at home on the weekends while others are out having fun. Mr. Right is not going to show up at your doorstep and ring your bell. You’ve got to put yourself out there and take some chances. I’m just saying. – Straight From Your Gay Best Friend

You can follow Terrance Dean on Twitter, HERE!

Make sure to get your copy of my new book,  Mogul: A Novel (Atria Books – June 2011; $15). It is available in bookstores everywhere, and on Amazon, click, HERE!


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