Let me preface this by saying, I am the most flirtatious and charming guy you will ever meet. I don’t say that to brag, but to explain my nature. I have been a flirt since I was a small boy – it is my nature. I aim to be charming with everyone – from a hottie walking down the street, to the freakin’ mailman. It doesn’t matter if the person is 8 or 80, I enjoy making people smile and laugh and take joy from the positive feedback I receive. This isn’t done to get someone in bed, or even start a relationship – it’s just to share in a little positivity.

I have had to sit back and evaluate this part of my personality in light of my new relationship. It adds an entirely new element to “my nature.” Now, I have to deal with feelings of guilt, jealousy, and more. Is it right for me to flirt with a member of the opposite sex? Is that something that can coincide with a healthy relationship? Will it cause fear and doubt in the mind of my spouse/girlfriend? Is it okay to flirt and be charming as long as the subject is someone that I would have no interest in (someone too old, too young, wrong sex, etc.) ?

Is it fair to the object of my flirtation? I have no doubt that my current relationship is “the one.” Should the fact that I am “off the market” make it cruel or mean of me to give false hope to someone else?

If I were single, would this change the answer to any of those things? If I am viewing all these flirtations as superficial, fun diversions – it that fair to the flirtees?

Or, is the act of flirtation innocent and something that should be enjoyed by all involved? How do you go about doing that yet still making it perfectly clear that it is just simple hi jinx and nothing more?

I am guessing that 1) flirting with others while in a relationship is something that should be curtailed whether you mean it innocently or not, 2) flirting with others while not involved is something that is fun, but you need to be careful to not mislead someone. What are your thoughts?