Dating a Friend's Ex: Should You Date a Sibling/Mate's Ex?

Whether you’ve always had a connection or whether there’s something new brewing between an ex-flame of your friend or sibling, can you really take things further? Would dating a friend’s ex be awkward? Would it end the friendship/ Can you really date your friend’s sibling or friend’s ex without any weirdness?

Here are a few things to consider:

Can you date your sibling’s or friend’s ex? Technically, yes. You can date whoever you want if they’re of legal age and fully able to consent.

Socially incestuous dating happens when the same group of people interact a lot. It can occur between different friend groups, in a small town where the dating pool is shallow or when current partners or exes have family members in common.

On the flip side, it can be seen as tacky and desperate to date someone your friend dated.

Dating a sibling’s ex is even trickier. Especially when it comes to family gatherings, particularly if your sibling is less than supportive.

When I was a fresh-faced, naïve eighteen-year-old, I succumbed to the charms of an older guy who had dated my mum’s best friend. Now, that was messy.

Dating a friend’s ex? Yes, you can. But should you?

Before you have a conversation with your friend, make sure you want to risk the friendship for their ex. Do you have similar values? Do you want the same things in life? Are you compatible? The chances are you will have gotten to know this person while they dated your friend so, ultimately, the risk is up to you. Make sure you’re not being used to get back at your friend.

But, if you care about your friend and don’t want to lose the friendship but you really want to date their ex, here are some tips on how to broach the subject and hopefully come out of it with your friendship still intact.

Communicate openly and honestly: Before pursuing anything with your sibling/friend’s ex, have an open and honest conversation with your friend. Discuss your feelings and intentions, and make sure they are comfortable with the idea.

Respect their feelings: Understand that your friend or sibling might have lingering feelings or concerns about their ex. Be respectful of their emotions, and if they express discomfort or disapproval, consider whether pursuing a relationship is worth potentially damaging your friendship.

Give it time: If the relationship has recently ended, it’s wise to give them time to heal and move on before pursuing a romantic relationship with their ex. Jumping into a new relationship too quickly might be hurtful.

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Consider the nature of the breakup: If the breakup was amicable and both parties have moved on, it may be more acceptable to explore dating a friend’s ex. However, if the breakup was messy or involved betrayal, it’s crucial to tread carefully. If their ex was a walking red flag, you might be setting yourself up for heartbreak.

Ask them for their blessing: If your sibling or friend is genuinely supportive and gives their blessing for you to date their ex, it can help mitigate potential conflicts. However, ensure that their approval is sincere and not coerced.

Maintain boundaries: Establish clear boundaries with both your sibling or friend and their ex to avoid any awkward or uncomfortable situations. Being transparent about your intentions and respecting everyone’s feelings is crucial.

Be prepared for consequences: Understand that dating a friend’s ex may have consequences, even if you navigate the situation carefully. It could strain your friendship or cause discomfort within your social circle. This might also mean you and your friend take a break from each other, only see each other when their ex isn’t around, or lose them. You might also lose your social circle completely. Family gatherings might be tense and awkward for a while and be prepared for people to take sides.

Consider the significance of the relationship: If your sibling relationship or friendship is extremely important to you, weigh the potential romantic relationship against the value of this connection. Sometimes, dating a sibling’s ex may not be worth it.

Take responsibility for your actions: If you decide to pursue a relationship with the ex of someone close to you, be prepared to take responsibility for your choices. If conflicts arise, address them openly and honestly rather than avoiding the issue.

It’s essential to approach these situations with sensitivity, empathy, and self-awareness. Every relationship is unique, and the factors involved can vary significantly.

Ultimately, the decision should align with your values, priorities, and the overall well-being of everyone involved. If in doubt, seeking the advice of a trusted friend, family member, or counsellor can provide additional perspectives.