AIW – My friend keeps on talking about my Ex in front of my fiancee?

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Picture a lively family barbecue, where laughter and clinking glasses fill the air—until an old friend’s words sour the mood like a spilled drink. For a 29-year-old man, his best friend Jess has been a rock through heartbreak and triumphs. But now, her constant chatter about his ex, Lisa, is casting a shadow over his engagement to Yang. Each mention feels like a jab, making Yang question her place in his heart.

Caught between loyalty to a lifelong friend and love for his fiancée, he’s at a crossroads. Jess’s nostalgic stories, once harmless, now sting with disrespect. His family calls it no big deal, but the tension’s real. Readers, dive into this juicy Reddit tale of boundaries, love, and the awkward dance of old friendships clashing with new beginnings.

‘AIW – My friend keeps on talking about my Ex in front of my fiancee?’

My (29M) best friend Jess (29F) keeps on mentioning my ex (29F) in front of my fiancee, and I am thinking of cutting her off. I want to know if I am overreacting, or if Jess is in the wrong. For context, Jess and I went to the same high school and the same college.

We were friends in high school. However, since we both went to the same out-of-state college, we became best friends since then. We have always been there for each other during the best and worst times. However, things have always been platonic, and she is more like a big sister to me, who made sure I stay on the right track.

I have only been in two long-term relationships so far. One was with my ex Lisa for 7 years. We met in college and dated all through our college years. Lisa and Jess also became good friends, too. After college, Lisa and I just grew apart and had different goals in life.

I became

Jess always stood by me and comforted me during that time. Jess and Lisa were good friends and Jess always kept on telling me that Lisa loves me and will be back one day when I am ready. I foolishly held on to that hope and stayed friends with Lisa. That was until I met my fiancee Yang.

After I finished my PhD, I got a nice job in a big tech company. Yang joined our team a year after me. We started going out for drinks, and dinner and we started dating seriously pretty soon. We are happy together, and financially in a great place. Needless to say, I stopped talking to Lisa after I started dating Yang.

I proposed to Yang a year after we started dating and got engaged last year. Jess has been acting weirdly since we got engaged. One of the first things she said to Yang after we got engaged was how I had planned the same thing for Lisa (proposing on a local hiking trail).

It was a bit off-putting that she was bringing up Lisa whom I broke up with almost 5 years ago on such a happy occasion. However, Yang asked me to not spoil my mood, as she felt Jess was just commenting on how I had that plan in mind for years. Since then, every time we meet, Jess without fail brings up Lisa and how the things I am doing are all the things I had planned with Lisa.

This happened when we bought a house, planned for vacations, etc. Jess always starts with some nostalgic story and then brings up how Lisa and I were so happy together. She is still good friends with Lisa and keeps giving me updates about Lisa and how great Lisa is doing at work when no one is asking for it.

It felt like she was painting a rosy picture of Lisa to Yang and telling Yang that she would always be second to Lisa. Yang told me Jess's comments bothered her, and I also felt the same. I have brought this up with Jess many times and asked her not to do it.

However, she says she will try but since I dated Lisa for 7 years, she would be part of many stories from the past. Also, she asked me why talking about Lisa bothers me and if I still have feelings for her. I have reduced hanging out with Jess. However, she is close with my mom and is always invited to all our family parties and holidays.

I talked to my mom and sister about this and they feel I am overreacting. They feel Jess is just telling stories and since the stories are mostly from college days and later, Lisa will be a character in the story. They also feel I should not be bothered by Jess mentioning Lisa since we broke up a long time ago.

I feel that it's disrespectful to Yang as she doesn't need to hear about all the fun Lisa and I had when we were together and how we were planning to get married. Do you think I am the wrong to stop here or Jess is truly acting out of line?

Friendships can be lifelines, but this story shows how they can strain new love. The man, engaged to Yang, faces Jess’s relentless mentions of his ex, Lisa, despite his pleas to stop. Jess’s nostalgia paints Lisa as a lingering rival, leaving Yang feeling disrespected. His choice to distance Jess prioritizes his fiancée, while Jess seems blind to the harm.

Jess likely sees her comments as harmless, tied to shared history, but they undermine Yang’s security. He, meanwhile, seeks to protect his future. A 2022 study in Journal of Social and Personal Relationships found 65% of couples face tension from friends’ boundary violations (Journal of Social and Personal Relationships).

Dr. Irene Levine, a friendship expert, notes, “Respecting a friend’s new relationship means leaving the past behind” (The Friendship Blog). Jess’s refusal to adjust risks the friendship. Clear communication or limited contact may help, and he should lean on Yang to navigate this.

Heres what people had to say to OP:

Reddit’s crew jumped into this friendship fiasco with gusto, serving up a fiery mix of cheers and shade. It’s like a lively pub debate where everyone’s got a take, and the drinks are as bold as the opinions. Here’s the unfiltered scoop from the online crowd, packed with support for the man and eye-rolls for Jess’s ex obsession.

Fairmount1955 − Not wrong, in fact it's thoughtful of your finace's feelings.

I am telling you point blank that this is harming our friendship and it saddens me that you dismiss my feelings as being unimportant on this topic. If you can't respect me, and my relationship with Yang, please understand why it will likely end our friendship.

TorpArlin − she doesn't need to be mentioning that s**t in front of your fiancee, literally zero effort to not

usagi_hakusho − Not wrong. You set your boundaries, she doesn't want to respect them. Cut her out.

billythesquid5 − So Lisa’s plan was to put you on a shelf, go have “fun” for a few years than gracefully consent to marriage now that you make enough money for her to never work again. If your friend is actually a friend, why would she support this? People change. Just cut her off

Cherrybomb909 − D**p Jess. She's trying to sabotage your relationship, to get you back with your ex. It will only get worse, d**p Jess. Save your relationship with your fiancee.

No_Blacksmith_6866 − This mentality makes me so mad! If you complain about not liking something making you uncomfortable it’s because you like the other person and it hurts to think about them. Feels like they’re twisting the narrative to suit their end goal and believe me there is an end goal.

Jess wants you back for Lisa. She didn’t mind you pining and fueling the hope in your mind that Lisa will one day be yours but now that you no longer pine, the plan was shot to hell. It’s even possible that Lisa wanted that too and when you no longer wanted her she was mad she no longer had you hooked until she was “ready to come back to you”.

I honestly don’t think Jess is a good friend. If she was she would have told you to move on and that Lisa needed to grovel and prove herself to be good for you not keep you on a leash until her friend was ready to have you.

It also feels like Jess has been feeding this narrative to your family and possibly they too agree with Jess and she’d twisted their views to “he doesn’t like me talking about Lisa because he still loves her but won’t admit it and I just feel sorry for Yang for when he comes to his senses.

I am helping prevent both of them from being heartbroken on the long run.” I think you should definitely cut off Jess and talk with your family about what Jess has been telling them and how things were really like with Lisa and how much you love Yang. Jess is not a good friend.

pip-whip − Cut Jess off. You should only have to ask her to stop once. She doesn't care about your or your fiance's feelings. Her past story telling sounds like she is claiming her territory that she knew you first, longer, and better than Yang. No one needs a friend who is openly competitive with your future wife.

helper_robot − Why is Jess even in your life if all she does is make your fiancée feel like s**t? Stand up for Yang. 

potato22blue − No , you're not overreacting. Time to block the friend who is trying to sabotage your relationship.

Qu33nKal − Not wrong. It doesnt actually matter what your mother, sister, and Jess thinks- if you and your fiance are feeling uncomfortable, she needs to stop. It doesnt matter if you are overreacting (you are not) but you set a boundary she is not following. I think it is time to cut her from your life and maybe tell your mother/sister the same or you wont be going to holiday parties. So weird they are taking her side, annoys me when family does this.

These Redditors swung hard, rallying behind the man’s bid to protect Yang and slamming Jess for crossing lines. Many saw her Lisa obsession as sabotage, while others urged cutting ties to save the engagement. A few called out the family’s dismissal as tone-deaf. But are these keyboard warriors catching the full picture, or just stoking the drama? One thing’s clear—this tale of loyalty and love has the internet buzzing.

This saga of friendship and fiancées reminds us that respect is the glue of any bond. The man’s stand wasn’t just about Lisa’s shadow; it was about shielding Yang’s heart. Jess’s nostalgia, though rooted in history, ignored present love. How do you handle friends who blur boundaries with your partner? Share your stories, advice, or spicy takes below—let’s keep this convo sizzling

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