A certain woman has been on your mind for quite some time. With a personality and body that make you lose focus, she is your ideal partner. Or so you think. The problem is that her former boyfriend and
 your best friend are the same person. So what on earth do you do? There are many factors to consider before you even begin to fathom a relationship with her.
Your Relationship With Your Friend

Some men form a bond based on trust and mutual respect. If that is the case with you and your best friend, you may want to step off and look for another woman. If the friendship has endured since grade school, for example, why would you risk it over a woman?

No matter how good she is, she cannot replace what you have with your best friend. The sex is not worth it alone, nor is the emotional investment. A best friend is a precious commodity that will endure a lifetime, provided you do not sleep with a woman he once cared about.

There is another type of best friend that men have, of course. That would be the fun but sick and depraved kind. The one who you would team up with for a three-way or compare a sexual conquest with. Could he be the same best friend as above? Perhaps, but the chances are slim. Because the same best friend is also the kind who would be open to the prospect of you and his ex as an item.

The fact of the matter is that some men have a wolf pack mentality on the subject of women. We want our pack to score often and revel in the unspoken endorphin rush we receive when we date (and sleep with) the same woman. I equate the misunderstood phenomenon to an episode of good fortune passed on to your best friend. You got some, so you want the pack to get some as well.

But some men do not like to "share." And when genuine emotion is at play, the situation could become complicated.
Your Relationship With His Ex
To determine the nature of his relationship with his ex, you have to be an expert judge of character. The stereotype of man as defective communicator is often accurate. Even our best friend may not be aware of how we feel about our ex. If you suspect that to be the case, you should play archaeologist and dig for information. Did the relationship end on a sour note? Who left whom? Did he love her or was she a mild interest that he had to gratify? Better yet, does he respect her?

You know how some men are -- all dog and player. I suspect that type may not have a problem with your affection for his ex. But then again, his real nature could emerge if you make a move and he could become possessive and resentful.
How Long Since The Break?
Even if your best friend had a close bond with his ex, there is still hope for you. The more time that has passed, the less painful and more palatable it will be for him to deal with your interest in her. If they broke up last week and you want to make a big move today, you could be in for it. But then again, if he discarded her and has another woman on his mind, you could be free and clear.

Time is a subjective thing. Some men have a one-year rule with their best friend. Some place a five-year moratorium on dating an ex. And then you have the group of men for whom the subject is taboo. They adhere to a strict code of honor set in stone: no matter the circumstance, an ex is never to enter the radar screen. Hardcore but definitive and effective for some men.

Why should it be a taboo subject?


Why Should It Be Taboo?
My opinion is that a woman is not a commodity, so why the restriction? As long as the intention is honorable and the interest sincere, a best friend should be free to explore a potential partner. She could be the one, after all. No best friend should be restricted from that possibility, given the proper time to heal and move on.
Your Approach
Even if your best friend has given you his proverbial blessing, be sensitive and take your time with his ex. As foreign as it may be, sit down and have a heart to heart with him; be a man and face the music. Tell him how you feel about him as a friend and that you would never want to sacrifice that for anyone.

Divulge your genuine interest in his ex. Stay away from your physical desire for her, as men are protective about a former bond with the anatomy of an ex. A gentleman can finesse his way out of danger and assuage his best friend. The point is to be prepared for an extreme reaction, from rage to silence.
The New Relationship
One giant supposition I have made in the scenario at hand is that the ex has an interest in you. So now we can assume that your best friend is cool and you have made a move. You start to date and an exclusive relationship is around the corner. Out of respect to your best friend, there are a few steps you should take:

Limit his exposure to you as a couple: Make a concerted effort the first month or two, to ease him into the new reality.

Limit your public displays of affection: Once you start to socialize as a couple, you may not want to make out in front of him or tap that behind. Display your affection with class and not in a gratuitous manner.

Do not complain or seek his advice: It could depend on what type of person he is but as a general rule, I would not advise you to go into detail about the relationship. If you have a problem with her behavior for a particular reason, deal with it on your own. He had to and so should you. A discussion about her could be painful.

No sex talk: Unless your best friend should fall under the depraved category, refrain from pillow talk. Gossip with another friend who has no association with him, if you must.

An obstacle or two is inevitable. His ex (and your new woman) may need reassurance now and then that she has not come between the two of you. Both you and your best friend must make an effort to let her know that the opposite is the case.

On the other hand, she may need a lesson in class in order not to flaunt the relationship in his face. You need to take a stand from the outset to ensure that everyone is on the same page. A hidden agenda or unspoken opinion could destroy more than one relationship.

Consider what is at stake, communicate and check your motive before you start.