Reader question: Is it ever OK to date a friend's ex?
This is quite a controversial topic, and perhaps I will have some people disagreeing with me here, but my answer in short is . . . maybe? I think a lot of people would see this question and immediately say, "No, not ever, not under any circumstances," which I get! We're taught to follow a moral code that is black and white, and usually dating a friend's ex sit firmly on the not OK side. However, I am a firm believer that emotional conflicts can never be absolute. There are a few factors to consider here.
How does your friend feel?
Figuring out how your friend feels about it is clearly the most important factor to consider. I think it's a little single-minded to assume that dating a friend's ex is wrong without consulting that friend. I have exes that I would be totally fine with my best friends dating, but there are others where I could not deal if they were dating a friend of mine. It's not a good idea to ever assume when it comes to touchy emotional subjects, so make sure you are open and honest from the get-go.
I think no matter what 'kind' of ex, this person is to your friend, so having a conversation is important. Whether this is an ex-boyfriend of three years or a someone your friend slept with for a few weeks, if you care about your friendship at all, you'll have this chat before anything happens. I think most of the hurt that comes from friends dating exes is the betrayal that comes with it being a secret for any period of time. Make sure your friend has the option to give the green or red light before you do anything concrete.
Don't listen to outside opinions
Your friend's opinion is the only one you should be worried about. A lot of the time, other friends who aren't involved will have opinions on what is morally 'right'. Often friends will project their feelings onto a situation — they will imagine how they would feel if you were to date their ex. Don't listen to anyone except the friend in question. If they are fine with you dating their ex, none of your other friends need to get involved.
Friendship . . . or relationship?
Now, here is the part that may be controversial. I think if your friend says that they aren't comfortable, you have the choice between your friendship or your relationship with their ex. I think it's important to weigh it up (of course), but I have always found the notion of someone "owning" someone else for the rest of time after they have dated to be a little . . . unreasonable? Clearly, humans tend to gravitate toward those with complementary personalities, values and interest. It isn't completely out of the question that more than one person in a friendship group would get along with another person's ex.
Calling 'forever dibs' on another human just doesn't sit right with me. It's similar to the idea of 'girl code'. It implies ownership of a person, and is almost dehumanising for the person in the middle of the tug of war. What does matter though is being honest about your feelings to your friend and their ex. If you really do see a future with a friend's ex, assuming there's been a decent amount of time since their breakup, the best you can do is be completely transparent with your friend, and explain to them your feelings for their ex.
At the end of the day, it comes down to one question: What's more important, your friendship or this new relationship? Be honest with yourself and your friend and go from there. It's a tough situation, but no one will benefit from lying or betrayal. Good luck!