Many of us establish a set of dating guidelines for ourselves to determine who we date and how we'll behave. These might include rules such as not dating a colleague at work or not having sex on the first date. However, one of the dating commandments that's high up on most people's lists is "Never date a friend's ex" - and for good reason. It's very rare that you'll be able to keep both relationships working, and you may even end up losing them both.
Timing
The first issue to tackle is timing. Dating a friend's partner behind their back is an accident waiting to happen. Even if your eyes lock and there's instant chemistry between the two of you, do the decent thing and make sure that your new found love breaks it off with your friend before you act upon any of your feelings. Give yourselves a decent interval before you get together; the wounds may still be fresh some time later and jumping into something too soon will undoubtedly cause your friend distress and hurt. Make sure that they are positively over their ex and that there are no unresolved feelings lingering in the air before you make your next move.
Letting Them Know
Even if your friend and their ex broke up some time ago, you may feel that you are in an awkward position. However, no matter how uncomfortable you feel, you must be upfront about your feelings, don't even think about going behind your friend's back.
Ask them how they would feel if you were to date their ex; be honest about your feelings and try to be as open as possible. It may be that your friend is completely over their ex and has moved on in their life and does not see your new relationship as a problem. However, you must be open to the possibility that your friend may be hurt and upset about the idea.
Deciding Your Priorities
When dating a friend's ex, you run the very real risk that you will end up losing that friend, no matter how tactfully you have dealt with the subject. You have to ask yourself whether your new relationship with the ex is worth risking your friendship. Good friends are hard to come by, and you may decide that your friendship is more important than a relationship that may not even work out.
