Dating Best Friends Ex: A Friendship Dilemma

A 28-year-old man and his best friend have been inseparable since college, until one breakup turned into a very awkward kind of “what if.” He was there for her when she and Alex fell apart, and he watched the two of them pick up the pieces, side by side.

Then months later, Alex and the OP started getting closer. The chemistry became real, they confessed feelings, and now he’s staring at the messiest question possible: does he follow his heart, or does he respect the “girl code” his best friend has been loud about for years?

Because the person he wants to date is the same ex she said would be off-limits.

Original Post

So I'm (28M) and I've been friends with my best friend (27F) since college. We've always been close and shared everything together.

One day, she started dating this guy, let's call him Alex (30M), who I also became friends with through her. They dated for about a year before breaking up due to personal differences.

I was there for both of them during the breakup and supported them as best as I could. Fast forward a few months, and Alex and I started getting closer.

We found that we had a lot in common and enjoyed each other's company. Sparks flew, and we confessed our feelings for each other.

We decided to start dating, fearing how my best friend would react. I know she wouldn't approve due to her past with Alex.

However, I can't deny the connection I feel with him. Should I go for it and risk ruining my friendship with my best friend or listen to her relationship advice and let this opportunity go?

For background, my best friend has been vocal about her feelings towards me dating any of her exes in the past. She's always said it's a breach of girl code and would be hurt if any of her friends pursued a relationship with them.

However, I can't help but think that Alex and I could have something special together. I'm torn between following my heart or respecting my best friend's wishes.

What should I do? Really need some outside perspective on this one.

The Heart vs. Loyalty

This dilemma hits home for many because it raises the classic question: how far should friendship stretch when love is involved? The OP's friendship with his best friend isn’t just casual; it's built on years of shared experiences since college. The emotional stakes are heightened by her firm stance against dating exes, which complicates the potential romance with Alex.

Dating an ex is often seen as a betrayal, especially when the friend has been vocal about their feelings. The tension here isn’t just about romance; it’s about trust and loyalty. The OP's desire to pursue his feelings for Alex could mean risking a long-standing friendship, creating a moral grey area that many readers can relate to and debate over.

That “I supported both of them during the breakup” moment is exactly why this romance feels like it could either be fate or a betrayal.

Comment from u/AdventureSeeker23

YTA if you pursue Alex behind your best friend's back.

Comment from u/CoffeeBeanLover

Honestly, this is a tough situation. You should consider having an open and honest conversation with your best friend about your feelings for Alex. Communication is key in maintaining friendships, and she may understand your side if you explain it properly. NTA for developing feelings, but YWBTA if you don't talk to her about it.

Comment from u/MidnightDreamer

NTA. You can't help who you have feelings for, and it's natural to be drawn to someone you have a connection with. However, you should talk to your best friend and express your dilemma. Communication is crucial in resolving conflicts like this. Best of luck to you.

Comment from u/OceanicSoul123

Wow, this is a tricky one. I get that you have feelings for Alex, but your best friend's feelings matter too. Ignoring her relationship advice could strain your friendship. It might be worth discussing your feelings with her and seeing if there's a middle ground. YTA if you don't consider her perspective.

When the OP and Alex started getting closer after “a few months,” his best friend’s past warnings about her exes suddenly stop sounding theoretical.

Comment from u/TravelerAtHeart

YTA. Going after your best friend's ex, especially when she's expressed her discomfort with that situation, is not a great move. It could damage your friendship irreparably. Respect her boundaries, talk openly with her, and then make a decision. Don't just act on your feelings without considering the consequences.

It’s like the OP debating whether to secretly set up their best friend with their ex, without her knowing.

Comment from u/MoonlitSky25

Hmm, this is a tough spot to be in. It's understandable that your feelings for Alex are real, but your best friend's feelings are valid too. Before making a decision, try to have an honest conversation with her. Consider her perspective and then decide what's best for you and your friendships. Good luck, OP!

Comment from u/GuitarGuru99

YTA. It could create a lot of tension and hurt feelings. Consider your friendship first and respect her boundaries.

The confession part, where they admit they have feelings, is where the friendship math gets brutal, because her stance on Alex is already on record.

Comment from u/StarlightDancer88

NTA for having feelings for Alex, but YWBTA if you act on them without discussing it with your best friend. Open communication and respect for her feelings are essential in this situation. Be honest with her and see if there's a way to navigate this tricky scenario without damaging your friendship.

Comment from u/WildernessExplorer7

YWBTA if you pursue a relationship with Alex without considering your best friend's feelings. Girl code or not, your friendship should take priority. Have a heart-to-heart talk with her, explain your emotions, and see if there's a way to move forward that respects everyone involved.

Comment from u/CoffeeLover5555

Hoo boy, this is a sticky situation. Your best friend's feelings are important, but so are your own. Maybe it's time for a real heart-to-heart chat where you express what's going on and how you feel. Communication is key in navigating these complex emotional waters. Best of luck, OP!

Now he’s stuck choosing between the connection he feels with Alex and the years-long bond he’d risk with his best friend over the same guy.

What would you do in this situation? Share your opinion in the comments.

Caught in the Crossfire

The fallout from this situation could have ripple effects beyond just the OP and his best friend. If he chooses to date Alex, it could not only strain his relationship with her but also impact Alex, who might find himself caught in the middle. This adds layers to the already complicated friendship dynamics; it’s not just about one person’s feelings but how they affect a whole group.

Interestingly, community reactions are divided. Some readers empathize with the OP, seeing it as a chance for him to pursue happiness. Others argue that crossing this line could cause irreversible damage. This conflict highlights the complexity of human relationships and how difficult it can be to balance affection for friends with newfound romantic interests.

The Bigger Picture

This situation perfectly encapsulates the messy intersections of love and friendship.

What It Comes Down To

The situation faced by the OP is a classic tug-of-war between loyalty and love, especially given his best friend's firm stance against dating exes. After years of friendship and supporting both her and Alex through their breakup, it's understandable that he feels conflicted about pursuing a romance with Alex, despite the potential repercussions for his friendship. His emotional connection with Alex has grown, which complicates matters further, as it raises the question of whether personal happiness should take precedence over established boundaries. Ultimately, this dilemma reflects the intricate dynamics of human relationships, where the stakes are high, and the risks palpable.

He’s not just dating Alex, he’s rolling the dice on his best friendship.

Still worried about dating your best friend’s ex, even after her blessing? Read the AITA case where mutual friends judged it.