First of all you need to question why you are looking at any other guy than your boyfriend with dating on your mind. The fact that you're bored enough with your current relationship that you're considering what it would be like to date someone else suggests that you have some strong issues going on between you and your partner that are being ignored. Are they his issues or yours? Or do you feel that the relationship has gone just about as far as it possibly can? How is your boyfriend feeling about it? Do you think he is also starting to look at other women with a view to some kind of relationship? Or do you think he is completely unaware that there's a problem (or two) between you that needs to be sorted? If these things could be worked out, would you be happy to stay with him, or would you still want to move on to another man?

If you think he's completely unaware, then you need to talk to him. Tell him how you feel about things. Tell him that you don't want to be in the relationship as it is any more. If you think it can be worked out, then you need to come to some kind of understanding between you. If you aren't interested in working it out, then you need to make a clean break of it.

Now you've got your current situation under control, how are you going to approach dating your now ex's best buddy? Guys are different than girls, and whereas a girl's best friend would usually not want to upset her friend by dating her friend's ex, a guy may not see that as a problem. As far as he's concerned, his friend is no longer dating you, you are available and interested in him, and so why not! There are a few guys who would think about their friend's feelings, but not many! In the guys dating field it's every man for himself!

What you need to keep in mind is that it's very likely that your ex will have discussed you with his buddy, and buddy is likely to discuss you with your ex (if your ex is still speaking to him!). You also need to remember that buddy isn't particularly interested in what happened between you and your ex, as far as he's concerned, it's a done deal. So don't discuss your past relationship with him. Guys don't usually want to hear about the other guys you've dated anyway, and just because this ex is/was one of his best buddies, doesn't change that fact.

Although most guys won't turn your attention down just because you broke up with their friend, you have to be prepared that a few of them -- especially when it's a relationship that goes back to grade school -- will turn you away simply because they don't like what you did to their buddy. It won't matter to them that their buddy was in any way part of the cause of the break-up, they will only see that dating you would be a huge disloyalty to their friend. It won't happen often -- but sometimes, guys can be as close to their buds as girls can!