Whether you’re a guy or a girl, you know that you always pick your friends before a love interest.

What’s more, the cardinal rule of friendship is: you NEVER date a friend’s ex.

But what if you truly have unparalleled chemistry and compatibility with a friend’s ex?

Do you let it slide for social norms and run the risk of never finding anyone quite like him/her or forever wondering what could have been? Or do you jeopardize your friendship and risk being a social outcast by pursing your friend’s ex in what can only be a risqué move?

Whatever your decision may be, below are a few do’s and don’ts and tidbits of advice that can help make the process as drama-free as possible:

DO: Ask yourself if the “Ex” is worth it?

In such delicate situations, it’s important to set raging hormones aside and really ask, “is this girl/guy WORTH the trouble?” Is the attraction something you’ve felt with other people or truly something rare? Would this girl/guy be worth losing your friend? Would you feel guilty later on?

There’s no point jumping in fire if you find yourself equally attracted to five other people in your life in addition to your friend’s ex. After all, 50% of marriages fail and that number is much lower than non-nuptial relationships!

DON’T: Immediately make a move

Timing is key.

Making a move right after a breakup can make you the rebound for the  love interest and a horrible friend. Each scenario is different so it’s important to see how distraught your friend is and how available your friend’s ex is.

A rule of thumb is to wait until your friend starts checking out other people and starts showing interest in dating.

DO: Ask your Friend for Permission if the Breakup is Recent

If the breakup is recent, then the the best way is to confess your feelings to your friend. Express how you are interested in his/her ex and you don’t want to jeopardize your friendship.

Ask if there will ever be an appropriate time to ask the ex out and make sure to LISTEN to your friend.

If your friend gives a timeline (e.g. “It’s cool, but just wait for 3 months”) then STICK TO IT.

If your friend is unwilling to cooperate with your plan (e.g. “I can’t believe you can even ask me that! What kind of a friend are you?”), then consider waiting until the wounds are no longer fresh OR decide what’s more important to you–an established friendship or a potentially successful (or unsuccessful) relationship?

DON’T: Ask your Friend for Relationship Advice

If your friend gives his/her blessing–don’t EVER ask for relationship advice.

Trying to get details on what their ex likes and doesn’t like or asking for advice when you think something is wrong is just rubbing salt in their wounds.

DO: Disclose the Relationship to Your Friend

The worst thing you can do is hide your relationship from your friend and let him/her unexpectedly find out (à la Joey & Rachel). If you’re serious, then disclose the relationship to your friend and emphasize that your friendship is very important.

DON’T: Go over-the-top with the PDA in front of Your Friend

There’s nothing more tacky, tasteless or rude than making out and engaging in PDA in front of your friend.

Make sure your friend NEVER feels like the third wheel or just plain awkward in your presence–especially if their breakup is recent or your friend is not over the broken relationship.

When all is said in done, always remember that in 99 percent of cases, your friendship WILL change. Dating a friend’s ex makes it awkward for the friend so just make sure the ex is worth it!

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