Should I Tell My Best Friend Im Dating Her Former Crush?

A 29-year-old woman is best friends with a 28-year-old woman, and for nearly a decade they’ve treated each other like safe ground. Then the safe ground turned into a landmine.

Six months ago, OP started dating Alex, the man of her dreams. The twist? Alex and her best friend Emily went on a few dates before, it fizzled out, and Emily always spoke about him like he was still in the room. Now Emily’s admitted she still has feelings and regrets it never worked, while OP has been dodging every question about her love life.

So the real question is whether OP tells Emily the truth, or keeps quiet and hopes time fixes what it already broke.

Original Post

I (29F) have been best friends with Emily (28F) since high school. We've shared everything - dreams, fears, and crushes.

About six months ago, I started dating the man of my dreams, Alex (31M). He's amazing, and we're incredibly happy together.

However, before Alex and I got together, he and Emily went on a few dates, but it never progressed beyond that. She always spoke highly of him, but he ultimately chose me.

I've never told Emily that Alex and I are now in a serious relationship. I know if she finds out, she'll feel hurt and betrayed.

For months, I've dodged questions about my love life, making up excuses to avoid revealing the truth. Recently, Emily confessed that she still has feelings for Alex and regrets that their relationship didn't flourish.

I'm torn between telling her the truth and potentially breaking her heart, or keeping our relationship under wraps to spare her feelings. So AITA?

The Complicated Nature of Crushes

This scenario dives deep into the emotional minefield of friendships and unrequited love. Emily, having once dated Alex, likely still harbors feelings, making the OP's decision to date him feel like a betrayal. The fact that they've been best friends for nearly a decade complicates things further; their shared history adds layers to any potential fallout.

Readers are likely torn because on one hand, they can sympathize with the OP's desire for happiness, but on the other, they understand the unspoken rules of friendship. Keeping such a significant secret could easily lead to feelings of resentment and mistrust, especially when love and friendship collide in such a delicate way.

Comment from u/banana_hammock98

Comment from u/penguin_lover77

Comment from u/coffee_queen123

Emily and Alex already had a “few dates” history, and OP’s silence is basically that chapter getting erased in real time.

OP says she dodged months of questions about her love life, but Emily just confessed she regrets how things went with Alex.

This is similar to the Reddit debate over whether to date your best friend’s crush.

The Community's Divided Reaction

The Reddit community's reaction to this dilemma showcases how varied perspectives can be. Some commenters might argue that honesty is the best policy, advocating for transparency, while others could empathize with the OP’s choice to keep her relationship under wraps to avoid hurting Emily. This split reflects how differently people navigate social boundaries.

There's also the question of timing; if Alex and Emily had a messy breakup, the OP's timing could be perceived as insensitive. But it’s also worth considering that feelings evolve, and the OP deserves love too. In this case, the balance between protecting a friend’s feelings and pursuing personal happiness creates a fascinating debate about the ethics of friendship.

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Comment from u/gummybear_junkie55

The moment Alex becomes “serious” with OP, Emily goes from almost-dating to watching her past feelings get replaced.

Now OP has to decide if telling Emily about Alex is the kind of honesty that heals, or the kind that explodes their friendship.

We're curious to hear your perspective. Share your thoughts in the comments.

The Takeaway

This story highlights the challenging intersection of friendship and romance, where the lines can blur and emotions run high. The OP’s decision to keep her relationship with Alex a secret raises important questions about loyalty and honesty. Can you truly be happy in a relationship if it comes at the cost of a close friendship? What would you do in this situation: keep the secret or come clean to your best friend?

What It Comes Down To

In this situation, the 29-year-old woman is clearly caught between her happiness with Alex and her loyalty to her best friend, Emily. Given their nearly decade-long friendship, it's understandable why she's hesitant to reveal her relationship, especially after learning that Emily still has feelings for Alex. This dynamic illustrates the emotional complexities of friendships—where one person's joy can directly impact another's feelings, creating a delicate balance that’s difficult to navigate. Ultimately, the decision to keep the relationship a secret might stem from a desire to protect Emily, but it also risks breeding mistrust if the truth comes out later.

Emily might not be mad about Alex, she might be mad OP let her think the story ended differently.

For a real love-triangle blowup, see what happened after someone hid dating a friend’s crush.