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Flirting Tales (page 1)
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135+ Flirting Tales ... 1st of 25 pages (next page)
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... Flirting Stories that have Fun Flirting Hints ...


Victoria is a buyer for a top New York fashion designer in Manhattan, New York. She is looking for a person who is into fashion. However, her problem is most men she encounters in her business are gay.

"I guess it goes with the territory," she mused. "But, most guys in the fashion business tend to be gay. I have plenty of gay guy friends, but not many straight guy friends". Help me"

Well, Victoria, our advice is to go where the real men go: sporting events come to mind. Why not, as a total change of pace, go buy yourself tickets for you and some of your friends (straight or gay) and tailgate a Jet's game!

Now, pay close attention to any man that will seem well dressed for the occasion. Tip: Look for good taste in shoes and watches, since they are likely to be wearing standard team logo attire. The accessories will indicate what fashion they don when not reveling in the manly man heaven called a football game.

Claude is a proctologist in Arlington, VA. He complains that that he deals with "assholes" all day long. All kidding aside, he is looking for a woman that he can really open up with, but is not sure how to go about flirting. After all, given the nature of his "introspective" work, flirting is not only inappropriate but also potentially business killing.

"What can I do? People don't like to sing Blue Moon when we are in the middle of an examination," he joked. "People simply want to get it (exam) over with as soon as possible and then they are out the door."

Claude would do well by staying in close touch with a professional association or similar group outside of his job. Like minded-professionals, especially those with their own practices, will find his line of work, less uncomfortable to talk about than if they were patients. Therefore, sometimes, if you stay within your work profession for flirting opportunities, it can work just as well as working outside of it.



Joe is a union ironworker in Pittsburgh. He works a very dangerous job climbing bridges and tall structures. At the end of the day, he wants to smoke pot to unwind and throw down boilermakers with his fellow crew members.

"Most women I flirt with are a little too butch for my taste," he said, sighing. "I guess it is the bars I hang out at with my friends." Problem is I am too tired to go anywhere when I have time off."

It sounds like Joe is not seeing the building for the I-beams. He just said he goes out every day after work and drinks and does drugs with his pals. He needs to cut back on his unproductive and unhealthy after work activities and build up the energy to go somewhere different, like a park, to meet someone that might actually help improve his lifestyle, versus encourage it.

Doug is a life insurance stiff in Memphis, TN. He describes his job as "boring as watching paint dry, but it pays the bills." In his spare time, he auditions for commercials and works part-time as an extra for a casting company that helps find extras for movies filmed on location in Memphis. He played "guy # 5 walking down the street" in the movie "The Firm," staring Tom Cruise. He frets that nobody notices him when flirting.

Doug is his own worst enemy. He dotes on his boring full time job, but Doug is much more than his actuary tables. He needs to see his full worth. So do you if you tend to define yourself by your nine to five. There is so much more to life then work. It is up to you to decide if you "work to live or live to work," as the saying goes. We live to flirt.



Jen in Jacksonville is very introspective and this often times causes her to feel down about stuff. Worse, she wants to dump all her unhappy feelings on a guy.

"I like to have a man as a sounding board," she said. "I mean... I want a man to listen to what I have to say."

Our advice to Jen is that her approach might be okay if you were married to the guy. After all, men pretty much have no choice by then. But, flirting-wise, you are not going to have any success. Flirting is about staying positive and most guys will avoid the "sky is crying" gal.


Jill, a technology analyst in Brea, California, is extremely busy and never finds the time to flirt with anyone, even at work.

"I guess I want a want a man that is just as busy as I am," she joked, "But the problem is that if they are just as busy as I am, then how would we have time to even flirt with each other? It is a no win situation."

There is hope for Jill and all the other workaholics out there. You simply have to make flirting a priority in your life. Remember, all work and no play makes Jack (and Jill) a dull flirt. So our advice is when you sit down to schedule your hectic life, make it a point to "flirt three times" during the week, wherever and whenever those opportunities present themselves. Do not put a specific time to it; just make it a task to flirt.


Carson is a field and track coach in Scottsdale, AZ, for high school boy's team. He is into competition and health. He loves flirting attractive and healthy women into joining him for an occasional run at the stadium.

"I don't like stay-at-home couch potatoes," he told "I like a woman who keeps up with me running the steps down at the track."

He describes his sure-fired flirting technique of approaching women who look athletic and asking them if they would be interested in participating in one of the charity runs he sponsors. He said it tells him two things:

1) they like to stay in shape, and;
2) they have a good heart. Sometimes it works, he says. Sometimes it doesn't. More often than not, it works.

Carson is wise in that he uses his flirting as a screening method. He can easily deduce if the women is even worth his trouble in the long run. Ah, the long run, something Carson is highly into, which also reminds us of a good point about flirting. Don't get winded early and give up, because when it comes to flirting, the tortoise usually wins.

Jack in Austin, TX, is huge Johnny Cash fan and spends all day strumming his guitar in the hope that one day he, too, will hit the big time. He also likes Hank Williams, Sr.

"I want a lady that appreciates good country music," he said, with a charismatic grin. "Not this Shania Twain crap... I'm talking old school country."

Jack is obviously looking for a down to earth cowgirl that likes to enjoy the roots of early country music. This tells us that he is not into the latest fads or hip trends, but likes tradition. One is best advised to flirt with a man like this by appealing to his sense of tradition. For instance a gal might ask him to a square dance.



Brad from Chattanooga, TN, is very serious when it comes to flirting and does not flirt lightly. When he meets woman he clearly plays up the troubled image, the scoundrel who never met the right woman, the bothered artist whose vision of the world nobody ever fully appreciated.

Whatever gets his flirting going is okay by us. However, be forewarned. Some people define themselves by the chaos in their lives because it makes them feel more alive in a perverse way. We all know someone that seems like they have to have some kind of disaster in his or her life. It is almost as if they wish it upon them. We say avoid such people. In Brad's case, it may only be act, but still, pulling a Van Gogh and mailing your severed ear to a lover, is not a great flirting move. And Brad just might be thinking along similar lines. If you are too, don't. Do you hear us?