Should I Set Up My Best Friend with My Ex? A Moral Dilemma

A 28-year-old woman refused to say “yes” or “no” to a simple idea, and it somehow turned into a full moral tangle. She and her ex, Alex, broke up amicably, and she still calls him a friend. So when her best friend Sarah hinted she wanted to meet someone special, OP started imagining a match.

Here’s the complication: Sarah and Alex have never met, and OP has not told Sarah that Alex is the person she wants to introduce. The plan is basically, “Let them hit it off,” but secretly. That means OP is juggling loyalty to her ex, loyalty to her best friend, and the awkward fact that one of these people is walking into a moment with missing context.

And once you realize OP might be engineering the meeting behind Sarah’s back, the real question becomes whether “good intentions” can still be a betrayal.

Original Post

I (28F) recently broke up with my long-term boyfriend (30M), let's call him Alex. The breakup was amicable, and we remain friends.

Now, my best friend (27F), Sarah, has been single for a while and has mentioned wanting to meet someone special. Here's where things get tricky: Alex and Sarah have never met, but I think they could really hit it off.

They have similar interests and values, and I believe they would be great together. I haven't told Sarah about my idea of setting her up with Alex because I'm not sure how she'll react.

On one hand, I want them both to be happy, but on the other hand, it feels a bit like meddling in their lives without their consent. So, would I be the a*****e if I secretly orchestrated a meeting between Sarah and Alex, hoping for a romantic connection, without Sarah knowing about my involvement?

The Ethical Quandary of Friendship

The OP's dilemma taps into a deep-rooted tension in friendships: loyalty versus honesty. Setting up a best friend with an ex without her knowledge raises major ethical questions. On one hand, the OP might believe she's doing her friend a favor by introducing her to someone she thinks could be a good match. On the other hand, it feels deceptive to withhold crucial context—especially since the ex is her former partner.

This situation illustrates a moral gray area where intentions clash with the potential fallout. If the friend discovers the truth later, it could not only hurt her feelings but also damage the trust in their friendship. Such scenarios resonate with readers because they highlight how complicated love and loyalty can be, leaving many to wonder if the OP's actions stem from genuine care or selfish motives.

OP’s breakup with Alex was calm, but the second Sarah starts talking dating, the mood shifts fast.

Comment from u/CoffeeLover42

YTA. That's a major breach of trust towards both Alex and Sarah. It's not your place to play matchmaker, especially with your ex and best friend without their consent. Total recipe for disaster.

Comment from u/GamerGirl_86

NAH. You're coming from a good place, but this setup could backfire badly. It's best to be transparent with both parties. Communication is key.

Comment from u/PancakeEnthusiast

ESH. While your intentions might be good, keeping Sarah in the dark about this could lead to a messy situation. It's best to have an honest conversation with her before making any moves.

Comment from u/throwaway98765

Well, it's a tough call. On one hand, you're trying to help them both find love. On the other, interfering in their personal lives without their knowledge isn't the best approach. Proceed with caution, OP.

Instead of bringing up Alex directly, OP keeps the whole setup idea to herself, which is where the trust starts cracking.

Comment from u/catwhisperer22

YTA. You should never set up your best friend with your ex, especially without her knowledge. That's a recipe for disaster and could potentially ruin your friendship.

This twist echoes the WIBTA dilemma of keeping a secret relationship with your friend’s ex-boyfriend, without telling her.

Comment from u/theunknown123

NTA. It's a tricky situation, but you have good intentions. However, make sure to consider all possible outcomes and be prepared for any consequences.

Comment from u/chocolatelover999

YTA. Playing cupid with your best friend and ex could lead to complications and unnecessary drama. It's best to avoid getting involved in their potential romantic connections.

The ethical mess gets louder when you remember Sarah has no idea her “special someone” is her best friend’s ex.

Comment from u/redditrocks786

NTA. You clearly want the best for both Alex and Sarah, but make sure to approach this with caution and ensure both parties are comfortable with the idea before proceeding.

Comment from u/pizzaparty4life

YTA. Meddling in your best friend's love life without her knowledge is a risky move. It's important to prioritize honesty and open communication in situations like this.

Comment from u/StarlightDreamer77

I think YTA.

By the time the comments roll in, both sides are basically arguing over the same thing, consent, and whether OP gets to control the outcome.

We'd love to hear your take on this situation. Share your thoughts below.

Community Reactions: Divided Opinions

The Reddit community's response to this post reveals the complex nature of romantic entanglements.

The Bigger Picture

This story highlights the delicate balance between friendship and romantic interests, leaving readers to ponder where the line should be drawn. The OP's situation resonates because it challenges us to think about our own values regarding loyalty and honesty in relationships. Would you want to know if your friend was setting you up with an ex, or would you trust their judgment? This scenario invites us to reflect on how we navigate the sometimes murky waters of love and friendship.

The Bigger Picture

The original poster's dilemma stems from a genuine desire to help both her best friend Sarah and her ex Alex find happiness. However, her reluctance to inform Sarah about her matchmaking intentions highlights the tension between loyalty and honesty. By considering a setup without Sarah's knowledge, she risks breaching trust, which could lead to significant fallout if the secret is uncovered. This situation underscores the complexities of navigating friendships and romantic connections, leaving many to question whether good intentions can truly justify deceptive actions.

Sarah deserves to choose a match, not be pulled into one OP arranged in the dark.

Secrets about your ex and best friend can blow up, just like this crush setup.