Welcome to the first of our "Head To Head Bloggers" series - two dueling opinions on the value of a wingman when you're out on the dating scene! First we hear from Carrie the Redheaded Writer, Then Dimitri from Dishing With Dimitri. Go!

CARRIE THE REDHEADED WRITER

How many times have you gone out for a drink and got cornered by someone who just won’t stop talking to you? Blah, blah, blah, they go on and on without letting you get a word in edge-wise. The next thing you know they are offering to buy you a drink, and before you can even reply, they not only ordered it, but have just stuck it in your hand! Wouldn’t most of us politely stand there, and sip our drink, feeling obligated? Of course, there are women who would smile at the guy, grab the drink and walk off with barely uttering a “thank you.” For the record, I am not one of them… Rude is rude, and two wrongs don’t make a right – at least that’s what my grandmother has always said.

Guys who do this, obviously, have a lot of confidence, are drunks, or own some very big conjones. Or, maybe all of the above! What do I know?

Here is where a wingman…er…uhm…your wing “woman” would come into play. She is your best girl and has known you since your under-age drinking days. She is the girlfriend who held your hair back when you barfed your brains out into the dirty toilet at the Sigma Phi Epsilon’s party. That is the girl who you are now looking for in the room while Mr. Cling-On goes on rambling and pressing you for your phone number, and repeatedly is asking why he can’t take you out on a date. Uncomfortable!

The bestie looks over and recognizes a horrified look when she sees one. You start casually playing with your right earring, the sign for “Get Dude Out of My Face!” She comes immediately over, grabs you by the arm and leads you away by saying, “I have someone I want you to meet.” In a smug way you smile at the guy and say, “Sorry, I have to leave.”

Now, maybe I haven’t been out with the right guy, but this is why it’s so important for a woman to have a female as their wingman. They get it. And why do they get it? Because most women have been in your shoes before – we all have.

If your guy friend had been there instead, he wouldn’t have understood the situation, nor would he recognize the panic look on your face. Why? Because all would see is a guy talking to you. And in his eyes, that’s harmless. That’s just the way guys are.

Women naturally feel very protective of their girlfriends. Men don’t have this instinct – unless they have an underlying interest in dating you - which is a whole other can of worms.

NOW DIMITRI'S PERSPECTIVE:

The Best Wingman Is Always a Woman (actually two women)

Behind every good pilot is an equally good wingman.

Don’t believe me, ask Ice Man about Maverick.

The fact is, when you’re cruising at a calm 700 m.p.h. 25,000 feet above the ground, in hostile airspace, you want the second best pilot with you covering your tail wing.

Same applies in dating.

Which leads me to this: The best wingman in the world is to have a wing WOMAN. Actually two or more wing-women.

I said it. I stand by it. I live by it. I eat by it.

How do I know this? In college I had two female roommates.

I lived with my wing women.

Both were very attractive, intelligent, fun-loving women with a penchant for making me look good. I know, I know, your imagination is probably running wild about what our nights must have been like behind closed doors…

It wasn’t Three’s Company nor was it a never-ending orgy with “no strings attached” (shameless plug for my last blog).

In fact, minus a few drunken nights of stumbling into the wrong room and accidentally lying down next to one of them, and putting my arm around her and….

… It was pretty innocent.

I learned a lot from the two of them but perhaps nothing more important than the fact that when a woman sees a man with two or more women, she is immediately wondering, “How did he manage to get two of them?”

And even though she may deny it, she has to find out for herself.

People always want what someone else has.

There were countless times we would go to a club or party and I would be there laughing and joking with them, only to look up and see a group of women staring at me like I was wearing a velvet smoking jacket, with pajama pants and slippers.

Hell your wing women don’t even have to say much. They can smile and talk to you about their boyfriends (without anyone hearing of course because if they do, you will immediately become “gay,” and women generally are not interested in Gay men. Or vice versa). All everyone knows is that they came with you and are leaving with you.

You have just achieved rockstar status.

You will be the envy of every man in the room and chicks love guys who are loved by other women.

Sure the naysayers will say, “But if he’s with two women, how can you trust him?” Or if he’s such a good catch why aren’t one of them dating him? I subscribe to the thinking of “anything worth talking about, is worth having.”

My wing women knew their role and played it well. They never talked about how great I was (much to my dismay), but instead chose to let me proceed unimpeded.

For the record it doesn’t really work both ways. A woman doesn’t need a guy wingman. All he’s going to do is get in the way. Most men won’t approach a woman with another man, so there is a drawback to being a wing woman. But guys are relentless. We’re always on the hunt. Consider a night as a wing(wo)man, a day away from the jungle.

My roommates and I “flew” many missions together and we always got our girl.

Which is exactly why I still keep a few good wing women in my life.