5 Questions to Ask Yourself Before You Date a Friend's Ex

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Written by Writer’s Corps member Demetria Osei-Tutu

You never think anything could breakup you and your best friend, but you could be wrong. Everyone has unspoken rules or guidelines around what is and is not okay to do in their friendship, otherwise known as bro or girl code. These guidelines might be as harmless as not giving unsolicited advice to more serious deal breakers like not abandoning your intoxicated friend at a party. But one of the most famous and universally agreed upon deal breaker is this: never-ever date a friend’s ex.

While we can all agree the ex-files is not territory we should be steering into, sometimes life happens and we fall for people unexpectedly. So, let’s say this is the case. You’ve fallen for your friend’s ex and your head is spinning with questions.

Will dating this person hurt your friendship?

Are you definitely feeling butterflies or is it something else?

It’s not like you’re actively looking to date someone from the ex-files but perhaps the chemistry you share with this person is undeniable so, naturally, you are considering what might be considered the unthinkable. for bravery, for ensuing drama. Below are the top 5 questions to ask yourself before your date a friend’s ex.

1. Will It Make Your Friend Uncomfortable?

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Let’s face it, some relationships end messy making it extremely difficult to consider that person anything other than off limits. If your friend’s relationship was rocky to begin with, you might be asking a lot of them to be around that person again. Beyond mutual unhealthiness, was their relationship abusive? If so, there are two things you should seriously contemplate:

Has the aggressor sought guidance: Have they received counseling from a counselor or other support group to change their behavior? Do you see evidence of lasting change?
This could be triggering: Your friend may never feel comfortable being around them again. The emotional and mental effects of mistreatment resulting from an abusive relationship may linger long after the relationship has ended.

Ideally, you won’t have to hide your new bae or your feelings for them from your friend so getting clear on their comfortability with your new relationship is paramount.

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Side Note: A history of violence or aggressive behavior is a huge red flag that should not be ignored. Even if your potential partner is kind and loving at the start of the relationship and actively seeking counseling to curb their controlling and aggressive behavior there is always the possibility they will repeat past behavior. Stay alert for any of the 10 Signs of an Unhealthy Relationship and seek help (call 911 for immediate assistance, campus security or the National Domestic Violence Hotline 1-800-799- 7233) if you feel unsafe or uncomfortable at any point.

2. How Long Ago Did They Breakup?

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There’s a difference between dating an ex from kindergarten and one from last month. Your friend might not care that you’re going out with their 8th-grade fling, they may even welcome the relationship with a little humor, but they will care that you’re dating an ex from a year ago or less. Breakups take time and closure, dating a friend’s recent ex can seriously impede their ability to move on. More than that, it may warrant more than a few side-eye glances you’re your mutual friends. Before you proceed, be sure both parties (your friend and their ex) have had ample time to get over each other.

Side Note: If you date a friend’s ex soon after the breakup, it might seem like you were waiting for your chance even if you weren’t which isn’t a good look in the long run or the short one.

3. Is Your Friend Over Their Ex?

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Was the relationship serious? Here’s the thing, the length of a relationship does not necessarily equate to the depth of feeling they had for each other. Serious relationships take time to get over. The last thing you want to do is start something with someone that has unresolved feelings for your friend or vice versa. Talk to your friend about the seriousness of their relationship with the person you’re thinking about dating. And when you do, pay attention to their body language and tone of voice. Remember, you know your friend better than anyone else, so you’ll know when they’re holding back their feelings and when they’re keeping it real.

Side Note: Communication is a must for every healthy relationship. If you leave the conversation still feeling unsure about your friend’s feelings than more conversation may need to be had.

4. Are They Doing It For The Right Reasons?

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No one wants to believe the person they’re into is dating them for the wrong reasons but, there are many levels to pettiness. It’s one thing to risk your friendship for a genuine connection that can’t be helped but what if they’re using you to get back at their ex (your friend). Some exes (unfortunately) do have ulterior motives and it’s important to suss them out as best you can before you become emotionally invested. Ugh, so messy.

5. Are You Willing to Lose a Friend?

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One of the most important questions you should ask yourself is this: is this relationship worth permanently or temporarily losing a friend? Sometimes friends will seem like they’re okay with something but will distance themselves from you later. It doesn’t necessarily mean they want to punish you but the reality of you getting close to their ex might (understandably) be too much. This isn’t meant to scare you but to prepare you for the possibility of suddenly being ghosted by your friend.

Side Note: Let your friend have as much space as they need especially if their actions point to some reservations about your new bae.

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Life is never black and white and there is no hard and fast rule that says you can never date a friend’s ex. Be thoughtful and considerate of their feelings and be as transparent as possible when discussing your desire to date that special person. You never want your friend to feel blindsided if you decide a relationship with their ex is worth a shot.