Is It Wrong to Set Up My Best Friend with My Ex Without Mentioning Their Past?

A 27-year-old woman thought she was doing something sweet, setting up her best friend Sarah with her ex, Alex. It sounded like a win-win on paper: Sarah is ready to settle down, and Alex is suddenly back in the picture, asking about Sarah like it’s fate.

But the twist is the part she wants to skip. OP and Alex broke up a few years ago on good terms, and everyone seems friendly. Still, Sarah would not know that the guy OP is pairing her with is the same person from OP’s past, which makes the whole thing feel like a trust test disguised as matchmaking.

Now the question is whether “amicable” is enough when Sarah’s feelings, and OP’s friendship, could get messy fast.

Original Post

I (27F) have been friends with my best friend, Sarah, for over a decade. We've shared everything and always supported each other through thick and thin.

Recently, Sarah mentioned being tired of the dating scene and feeling like she's ready to settle down. Coincidentally, my ex, Alex, just re-entered the picture and has been asking about Sarah.

Alex and I had an amicable breakup a few years ago, and we're on good terms. I think they would be a great match.

Would I be the a*****e for setting them up without disclosing that Alex is my ex?

This situation has all the elements of a classic love triangle mixed with the complexities of friendship. The OP's dilemma of whether to disclose her past with Alex to Sarah isn't just about honesty; it's also about the potential fallout if things go south. If Sarah ends up developing feelings for Alex and later finds out about their history, it could lead to a significant breach of trust. It’s a high-stakes game where one person's happiness could inadvertently hurt another's.

Moreover, this isn't just a casual fling; it's about Sarah, who is described as the OP's best friend. The stakes feel even higher when the bonds of friendship are on the line. If things go wrong, can the friendship survive? That's a question that resonates with many readers.

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OP has been best friends with Sarah for over a decade, so keeping Alex’s identity from her feels like a bigger deal than just a harmless little secret.

Why Readers Are Divided

The community's reaction to this matchmaking proposal showcases the deep-seated values we hold around loyalty and transparency. Many commenters have pointed out the ethical implications of withholding information about a significant past relationship. It raises the question: how much does one friend owe another in terms of honesty, especially when it involves an ex?

On the flip side, some argue that the OP has the right to pursue her own happiness without having to disclose every detail of her past. This kind of moral ambiguity is what makes the Reddit debate so compelling. Readers are grappling with their own experiences and biases, which makes for a rich discussion.

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That’s when Alex starts asking about Sarah again, right as Sarah says she’s tired of the dating scene and wants to settle down.

This is similar to the woman refusing to set her friend up with her ex, even after being told to move on.

The Complicated Nature of Ex-Relationships

What’s particularly fascinating about this scenario is how it highlights the murky waters of past relationships. The OP and Alex shared a romantic history, but that doesn't automatically dictate how Sarah should feel about him. It raises interesting questions about how we compartmentalize relationships and whether a past romance should linger over any potential future ones.

In many ways, the OP might be trying to give Alex a second chance through her friend, which complicates matters even further. It’s a risky move that could lead to heartbreak for all involved, and that tension adds a layer of drama that readers can’t help but engage with.

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Of course, the moment OP imagines Sarah finding out later that Alex was her ex, the whole setup turns into a potential betrayal story, not a romance story.

The Ethics of Matchmaking

This situation underscores a broader issue of ethics when it comes to matchmaking. The OP's desire to set Sarah up with Alex may stem from good intentions, but it raises questions about consent and informed choice. If Sarah's unaware of Alex's past with her friend, is she truly making an informed decision about entering a relationship?

Moreover, the OP's choice to keep this information under wraps could be seen as manipulative, even if unintentionally. This moral grey area is what ignites such passionate responses in the Reddit community. Everyone seems to have a stance, and that's what makes this story particularly engaging.

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So readers end up split, with some saying OP should protect Sarah’s trust, and others saying OP shouldn’t have to unload every detail about her past with Alex.

Share your thoughts and experiences in the comments section.

The Bigger Picture

At the heart of this narrative is a complicated web of friendship, loyalty, and the ethical dilemmas that arise when it comes to love. The OP's choice to potentially obscure her past with Alex could have significant implications for her relationship with Sarah. As readers weigh in on this dilemma, it raises an important question: how do you navigate the tangled web of friendships and past romances? Should the OP prioritize transparency, or is it acceptable to let her friend explore what could be a new romance without revealing everything? It's a conversation worth having.

The original poster's dilemma highlights the tension between friendship and romantic history, especially given her long-standing bond with Sarah. The fact that Sarah is feeling ready to settle down while Alex has re-entered the picture adds urgency to the situation, prompting the OP to consider matchmaking despite the potential fallout. This decision reflects a desire to see her friend happy but also raises ethical questions about transparency and trust, as withholding past details could lead to deeper complications if emotions evolve. Ultimately, it’s a balancing act between loyalty to a friend and the complexities of past relationships, making this a relatable and engaging scenario for many readers.

If Sarah finds out Alex was OP’s ex after the match starts, the friendship might not survive the “good terms” part.

Before you play matchmaker, read how lingering feelings complicate setting up Sarah and an ex.