Is It Wrong to Date Your Best Friends Ex After Getting Approval?

A 29-year-old woman is dating her best friend’s ex, and it’s turning into a full-blown friendship meltdown in real time. At first, it seemed like a win-win, Amanda gave her blessing, Jake and OP felt a real connection, and everyone was supposedly on the same page.

But after they started seeing each other casually, Amanda went distant and cold. When OP confronted her, Amanda admitted she was struggling to watch them together, even though she initially said she was okay. Now Amanda wants OP to end things with Jake to “respect her feelings,” and OP is stuck choosing between a longtime friendship and a relationship that’s only just starting.

Here’s the part that makes it messy: the approval came first, but the regret hit later.

Original Post

I (29F) have been best friends with Amanda (28F) since high school. We share everything and have always been there for each other through thick and thin.

Amanda dated Jake (30M) for a couple of years before they broke up last year due to personal differences. After their breakup, Jake and I started talking more and realized we had a strong connection.

He asked me out, and I said yes. Before things got serious, I made sure to have a conversation with Amanda to let her know about my feelings for Jake.

Surprisingly, she was very supportive and told me she had moved on and was okay with us dating. So, Jake and I started seeing each other casually.

However, recently Amanda has been acting distant and cold towards me. She barely talks to me and avoids meeting up.

When I confronted her about it, she confessed that she's struggling with seeing me and Jake together, even though she initially gave us her blessing. Now, Amanda wants me to end things with Jake to respect her feelings, but I'm torn between my friendship and my newfound relationship.

AITA for dating my best friend's ex despite her initial approval?

This situation raises the question of how well we really know our friends. The OP initially received approval from her best friend, but that blessing seems to have come with strings attached. Ama's subsequent regret complicates things, highlighting the emotional volatility that can exist in friendships. It's one thing to give a thumbs up when the idea is fresh, but once feelings get involved, things can shift dramatically.

The OP now finds herself in a position where she must balance her own happiness against her friend’s feelings. This tension is palpable and reflects a common struggle: how do we prioritize our romantic pursuits without sacrificing the emotional bonds we've built with friends?

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OP didn’t just “jump in,” she sat down with Amanda before things got serious with Jake, and Amanda actually sounded supportive at the time.

The Risk of Approval

The story's conflict centers around the concept of 'approval'—a tricky term that can mean different things to different people. When Ama said it was okay for the OP to date her ex, did she truly understand the implications? Or was it a knee-jerk reaction to avoid conflict? The OP’s dilemma reveals a broader truth about relationships: sometimes, the ‘okay’ isn’t as straightforward as it seems.

This ambiguity resonates with readers who’ve faced similar situations, leading to a heated debate on loyalty, love, and the boundaries of friendship. Can you genuinely support a friend's new romance if it involves someone who once held a significant place in their life?

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Then Jake and OP started casually dating, and Amanda’s mood shift was immediate, she barely talked to OP and avoided meeting up.

This loyalty debate echoes the AITA where someone dates their best friend’s ex despite her disapproval.

Emotional Fallout and Regret

The aftermath of Ama's approval is where the real drama unfolds.

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When OP finally confronted Amanda, Amanda admitted she couldn’t handle seeing them together, despite that earlier blessing.

Community Reactions and Divided Opinions

The Reddit community's response to this post reveals just how divided opinions can be on matters of love and friendship. Some users empathize deeply with the OP, understanding that love can often blur the lines of loyalty. Others side with Ama, arguing that no amount of approval can erase the emotional history between friends and their exes.

This debate touches on a universal truth: relationships are rarely black and white. Readers can’t help but project their own experiences onto the OP’s story, which makes it resonate even more. Whether they see it as a betrayal or just a complicated love story, everyone has a stake in the discussion, illustrating how intertwined our personal lives can be.

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Now Amanda is asking OP to end it with Jake, and OP has to decide whether her friendship matters more than the relationship she just found.

Share your thoughts and experiences in the comments section.

Why This Story Matters

In the end, this story serves as a poignant reminder of the complexities that come with love and friendship. The OP’s experience resonates with anyone who’s ever faced a choice that could jeopardize a close bond. What do you think? Is it ever truly okay to date your friend's ex, even with their blessing?

What It Comes Down To

The OP's situation highlights the often murky waters of friendship and romance.

OP is about to learn whether “blessing” really means “no strings attached.”

Wondering if you’re overreacting like the best friend who dated your ex without asking? Read this AITA about confronting a best friend over dating your ex.