How To Sleep With Your Friend's Ex

People are not things -- they are not owned. One does not come upon a person and pull grasses, throw stones and plant upon them the colors of one's empire as though they were a previously unknown land which can be possessed in the name of a distant monarch. People are individuals, full of their own desires and gifted with an agency equal to one's own. As such, one cannot lay claim to them, or take possession of them, or prohibit others from setting sail along their coasts. But people are emotional beings, too, and when they love and lose, they feel entitled to the ghost of what might have been -- whether this nostalgia is colored with grief, anger or remorse. It is for this reason that it is important to proceed with caution when one considers dating a friend's ex.

1. Consider your friendship.

Did your friend care deeply for this person? Did your friend suffer at their hands? The emotional turbulence experienced by a friend during their relationship and the amount of time that has passed will influence how they receive the revelation of your interest. You must take into account a number of emotional variables when you sit down to assess whether this undertaking is worthwhile. The likelihood that pursuing a friend's ex will negatively impact your friend is high, and you must prepare yourself for that reality. Expecting a friend to be cool with it is both naive and insensitive -- especially if little time has elapsed between their break-up and the birth of your interest. You must ask yourself whether the possibility of love or pleasure is worth risking the years of friendship you have accumulated with your friend.

2. Check in with your love interest.

However you got to know your friend's ex, it's important to verify that this person is equally interested in pursuing something with you. Sit down with them in private at the first appropriate opportunity and verify this. An appropriate opportunity, by the way, is not at a party where your friend or mutual friends may perceive something is going on. Be discreet. When you talk to your romantic interest, let them know that the situation is a sticky one because their ex is a friend of yours, and explain that this means that you are going to have to proceed with far more tact than is common in new relationships. You're going to have to determine when to disclose the relationship and to whom, and in what order, and manage all pertinent information even as your soul is crying out to scream one another's name from rooftops, as so often happens during the early stages of romance. You may even have to determine some boundaries in terms of group activities that involve your friend. Is your love interest capable of working with this?

3. Always stab in the face.

The first person who needs to know about your new relationship is your friend. This is especially important if you suspect that your friend will be injured by the new relationship. If you are going to stab someone you care about, always do it in the face. It adds insult to injury for a friend to go mad with suspicion and have to confront you about the new development -- or worse, to learn only from a mutual friend that they have been walking around with a knife in their back.

While you do not need to ask permission to date a friend's ex, as people are not possessions, you have gauged the intangibles and decided to pursue a relationship, so stand with conviction in your decision. Don't do it over text, but don't make a big production about having A Talk, either. No one likes the impending doom of a Talk over their calendar. Get together as you usually would and do it. You may have an inclination to bury the lede in a monologue about how much your friend means to you. Don't do it -- it may come off as insincere sugar-coating. A simple, "I want you to be the first to know that I am pursuing a relationship with _____," will do. Your friend may be frank in responding: allow this, even if it becomes a personal attack. Such things, underneath the abusive language, are merely expressions of grief. Try not to hold on to anything you hear, however unpleasant. Whatever your friend's reaction, let them know that you care about them and that you are aware that this is not a good situation. Let your friend vent. Do not argue.

If you are as terrified of facing a live-wire of emotion as I am, you may find the book Nonviolent Communication: A Language of Life by Marshall B. Rosenberg to be very useful. It will help you navigate the messy nature of such outbursts, find the hidden needs being communicated within, and show you how to let the other person know that you hear them.

4. Proceed with caution.

Do not expect things to be the same after you reveal your new relationship to your friend. Even if they took the news well, it's possible that they may need time to process the information. If you had made plans to do something together prior to the revelation, check in with your friend to see whether they're still interested in pursuing these plans with you. Be gracious if they imply that you should bow out. This is not the behavior of a dog with its tail between its legs -- it's an act of courtesy. A dog with its tail between its legs would not show its muzzle again, and you're not bowing out of your social circle in silence. You're communicating with the aggrieved party and making sure they are comfortable during this period of transition. Resist the temptation to break previous plans with your friend without talking to them. Face your friend, check in. If they do not want to see you, accept that, but don't just disappear.

5. Be discreet.

Without a doubt, your friend should be one of the first to know about your new relationship. It is unpleasant to be the topic of gossip and by letting the friend know in advance, you give them time to acclimate before the rest of the world finds out what's going on. This helps a friend avoid embarrassment, which should be a primary concern. A secondary concern is, of course, ensuring that the friends you share are not made uncomfortable by your new relationship or forced to choose sides. To this end, it is appropriate to avoid bringing your new partner to outings, parties, and other social gatherings where you may be seen by your friend and by mutual friends.

If you are in the same industry and must attend conferences or networking events with your new partner, ask politely that you both conduct yourself professionally with one another, stay apart throughout, and try to arrive and leave separately. Do not flirt on social media, check in at the same places, or post images that disclose information about your new relationship -- that's tantamount to snogging in public, and it's lacking in tact. Treat this transition period as one of mourning, and give it at least six months to get everyone used to the idea.

6. Check in with your friend.

From time to time, check in with your friend to see how they're doing -- not whether they're okay with your relationship, but how they're doing in general. As much as you can, be a friend. Show that your commitment to your friendship remains the same. In time, it's possible that this will guide your friend to a place of acceptance.

It's also possible that your friend will never recover from what they perceive to be a breach of trust. Having gauged the options at the beginning, you will be able to walk away from this ultimate rejection with the knowledge that you did what you thought was best for you, and even if your relationship with your friend's ex doesn't work out, you will be able to rest assured that despite the rather uncomfortable position into which love put the three of you, you always acted with courtesy with regard to the feelings of others.