'AITA for reacting 'wrong' to my brother's engagement? I knew his fiancee in high school.' UPDATED 4X (2024)

Here's where it gets complicated—I knew Jessica back in high school, and she was not what you would call a kind soul. She had a particularly nasty streak. She would not pay attention during class and always tried to cheat off of people's homework (and I assume got away with it). She tried (semi successfully) to steal my boyfriend. She bullied one of my best friends, calling her fat among other things.

This bullying worsened (if not caused all together) her eating disorder, and it's something I've never been able to forgive or forget. She is just one of those people who would just mess around with other people's lives like it's a game, and not something she is invested in. About 6 months ago, I had a heart-to-heart with Harry about Jessica.

I laid out my concerns and the history of her behavior, hoping it might make him reconsider or at least think deeply about their relationship. He said he'd consider what I said, but didn't continue the conversation much more. Since then, we talked regularly as usual, and things seemed normal between us. He didn't talk about Jessica often, but he didn't hide their relationship either.

I really was happy it sounded like it might be dying off though. I had no idea he was getting engaged to her until he announced it. I don't know if he has been telling other people in the family besides me, or if it was really just an abrupt decision. To make it worse, I am worried that he told Jessica about our conversation 6 months ago.

In her announcement on Facebook (annoying ring on hand photograph in tow) she wrote something like "I know not everyone in our family's are supportive, but we have each other and that's what matters".

So, he ignored my warning, AND he told her all about it.

Part of me wonders if I should just swallow my feelings for the sake of family harmony, but another part of me feels like I'd be betraying my old friend, my own values, AND my brother by pretending to be happy about this engagement. And I am bad at holding back my truth. So, AITA for feeling upset and possibly wanting to voice my concerns again, even though it might cause friction in my family?

Or should I just keep my feelings to myself and let Harry make his own decisions (and mistakes)? I just feel like there's nobody who I can talk about this with that will really understand.

Not long after posting, OP shared a small update.

Okay, thanks for all the responses people. I will take some advice:

Talk to mom and explain exactly what it is that Jessica has done and try to make her understand.

Talk to Harry about our conversation before and find out how much of it he shared with Jessica and how she responded to what I said.

Potentially talk to Jessica.

Seek therapy (someday haha).

I'm really not in a position to go no-contact with my family, and I still do want them in my life. I might post an "update" but also it seems like the rules are kind of strict on that which is fair. Message me or something if you want to hear what happens haha.

The comments kept rolling in.

Pretty_Lifeguard_1 wrote:

INFO: when was the last time you talked to Jessica? Lots of people who are a-holes during high schools change immensely during college or thereafter.

OP responded:

I haven't talked to her in at least two years (aside from kind of saying hello over speakerphone), but from her social media I really don't think she's changed. She's acting like an AH in general and a "pick me" towards my brother.

IamIrene wrote:

"afterwards my mom called me and told me that I was rude for not being excited."

No you weren't. You just weren't excited. You are entitled to your own feelings.

"and that I need to reconsider my behavior if I want to be invited to our vacation in the spring."

Oh, I see. So if you don't react the way your mother wants you to react she'll exclude you from family events. Got it. That's messed up.

I wouldn't worry too much if Jessica is aware of your conversation with your brother, if she is at least she knows you're wary (and rightly so). You are NTA for feeling the way you do or for your reaction to the news. Your mother is a bit of AH though...that's some Class A manipulation she's using.

Time will tell if things work out for your brother and Jessica or not but as long as you are polite without compromising your personally values, things should be fine.

If she decides to get nasty, don't hide your experience of it or your feelings about it, but also know that very often people outgrow their immature tendencies and she could become a very decent person. This whole situation reminds me of that movie, "You Again", lol.

OP responded:

Thank you. TBH I'm kind of used to this kind of thing from my mother, she likes to hold stuff over our heads. One time my siblings and I all got forced to miss a play we were going to see because "we weren't actually excited for it" even though I had been learning all about it and was really looking forward.

Part of me wonders if she just didn't want to spend the money haha. I'm not sure that this is what's going on here though. I truly do hope she's either outgrown it, or Harry sees her nasty side before the wedding.

fooftato wrote:

So in other words, your mother is passive aggressive, manipulative and abusive. And Harry is marrying someone exactly like your mother because it's what he's used to. Got it. My advice to you is to be polite but form a healthy life outside of your family and try to stay away and as much as you can and not let them control you. It's kind of a crap show as you can see. Can you do therapy?

See Also

'AITA for asking for separation after my wife told me to get over the loss of my friend?' UPDATED

That would honestly be great for you. Not because there's anything wrong with you, but because there is clearly a lot wrong with them and therapy would help you navigate how to deal with how cruel they were. Because what your mother did when you were kids with that play was honestly very cruel and I bet you have a lot more stories like that.

And it will help you deal with issues that come up as Messica integrates herself into the family and she and her mother power struggle as to who is going to be the meanest. Because there are going to be struggles. Let me tell you. And you are going to be forced to pick sides from one to the other.

And if you don't pick right there's going to be drama. Can you like move across the country or something? Haha. Honestly let your mother be nasty about you not going on the family vacation. Why would you even want to? It sounds like a nightmare. Tell her you can't get off of work or have too much school work or something. There's no such thing as a free family vacation if you know what I mean.

OP responded:

Hahaha, maybe you are right and I should do therapy. I had never thought about how Jessica is kind of like (a worse version of) my mom when it comes to manipulation...maybe that is a thing. I guess I don't need my family, but I do want that. Fortunately, the moving across the country this is already done, I went out-of-state for college while Harry and the rest of my family still live in our home city.

ParsimoniousSalad wrote:

NTA. Sadly, following her FB post, you know you still cannot trust Jessica, and you probably need to be more cautious with what you share with Harry as that goes to both of them. And don't voice your concerns again. He's made his choice. But you don't have to pretend to be enthusiastic either.

OP responded:

I'm so bad at holding my tongue, but thank you haha.

A few days later, OP shared another update.

So, a lot of people commented and sent me messages asking for an update to my previous post about unenthusiastic reaction to my brother's engagement announcement. Well, here it is. After reading people's replies, it sounds like the predominant opinion was that while I might not have been the AH immediately.,I would become one if I kept pushing too hard against my brother's relationship.

And I really don't want Harry to think I don't support him, or to not talk to me about personal relationship matters. So, I pretty much had decided to keep quiet and just go along with whatever Harry wanted. On Tuesday, he messaged me asking if I want to be a bridesmaid (in Jessica's wedding party) or a "groomsmaid" (in his wedding party).

After a little bit of back and forth, it became clear that he asked me because he knew I wasn't totally keen on Jessica, but still wanted me involved with the wedding. I was trying to be supportive so I said it would be great to get to know Jessica better by being a bridesmaid (though I wasn't exactly looking forward to the experience). I admit though, I had a little bit of an ulterior motive.

From what I know of Jessica, she completely changes how she acts based on who she is around (which is how she manipulated Harry into proposing, of course). I thought that, just maybe, if I could show Harry how Jessica acts with her "girls", he might reconsider his decision to marry her.

Anyway, on Thursday I got added to a Facebook messenger chat named "BRILLIANT BRIDAL B*TCHAZZZZ" wherein Jessica laid out her "ground rules" for being in the bridal party. They are, almost verbatim:

Participation in my bridal party is not just an honor; it's an investment. Be prepared to spend at least $1,000 on attire and accessories alone. I can make exceptions but only if you ask me.

I alone will dictate the narrative of my wedding on social media. Any premature posts, especially unflattering photos of me, will result in immediate expulsion.

Your weight will be monitored weekly. Anyone not fitting into their dress will be kindly asked to step down. This wedding will look picture-perfect, and I can't have you ruining the aesthetics.

From now until the wedding, I expect you to be on call 24/7. Wedding emergencies are real, and your commitment to solving them will be a true test of your friendship.

You will fund and organize a lavish bachelorette party in my honor. Think exotic destination, luxury accommodations, and Instagram-worthy moments.

You will have fun! Not just for your sake, but for me as well.

Upon reading this, I just burst out laughing. Screenshot, click! I think I might be able to convince Harry from marrying Jessica after all. I'm just deciding now if I should play it cool and act like the rules are normal but bring it up with Harry, or maybe show my mother because I know it would make her flip (and almost certainly forgive me for sighing when Harry told us about the engagement).

The comments came rushing in.

Bonnm42 wrote:

Wow.. if Harry was smart, he would RUN!

OP responded:

He has got to, right?

Crabbie_one_5443 wrote:

OP be smart. Tell your brother you changed your mind and when he asks why send him the screen shot and say you are not following these rules. You have to lead the horse to water but you can't make him drink. You can't make him see then he will just have to figure it out.

He will likely say those rules don't apply to you but you can say I don't think the bride would agree. Play it cool. Again the more you force them apart the closer they will become just to prove you wrong.

Haunting-Comb-9723 wrote:

Okay, if you want to play dirty, don't go to your mother and like "aha! See I told you!" Go to her crying and worried. $1,000 for clothes and accessories. Where are you going to come with that kind of money? And why should you lose all that money for a party? Remember, if you ask your parents to help pay for things that's at least $1000 out of their own pocket.

OP responded:

That's actually a really good idea hahaha, ask her to lend me some money, she'll ask why, and I'll tell her.

badpuffthaikitty wrote:

Sit back and watch the train wreck. Have you talked with the other bridesmaids yet?

OP responded:

Nope, they are all Jessica's friends. I honestly think they might be used to/expecting this. Though I don't understand how they could read those "rules" and think "sounds reasonable, count me in!"

badpuffthaikitty responded:

You must have one bad picture of her. Go for the instant disqualification route. Get fired, don’t quit.

OP responded:

Bahahaha, that's hilarious. I don't think I want to though, not yet at least.

Ten days later, OP shared another update.

Thanks for all the advice and support from my whole situation with my brother getting engaged to an incredibly annoying former(?) b*lly who has been manipulating him. I'm posting an update since a lot of people asked.

I'm gonna have to be a bit of a disappointment though. After my last post, a lot of people were suggesting that I should be tricky and go to my my mother and ask to borrow money to make the appropriate "investment" for being in Jessica's bridal party...I thought about that but realized it would be a little bit *too* over the top.

So, instead, I just sent a screenshot of Jessica's rules (and a couple other insane things she posted in the group chat) to Harry and asked for his advice, telling him "I know I said that I wanted to join the bridal party to get to know 'Jessica' better, but I'm worried it might not actually be good for me."

"Do you think I could bail and join your party instead?".

He called me instead of texting back and definitely sounded pretty surprised by what I showed him.

I'm certain that the side of Jessica shown in those "rules" and other messages (including a new one saying that if your BMI is over 22, you are out of the wedding) in the group chat is NOT the side of herself that she showed to him. We had a good hour or so of conversation about what things were like between the two of them, and I learned a lot about where he was coming from.

From what he told me, it sounds like getting married was really Jessica's idea. She had been going through some tough times later and apparently has struggled with depression in recent years. She's always wanted this perfect wedding and perfect married life, and she told him that it would make her feel better and fix all her issues of he proposed.

So, Harry, being the good person that he is, did it. He took pity on her even though he didn't really feel ready yet. He says he doesn't regret it though. She has been so much happier since the proposal, he said, and he is no longer worried about her running away, or harming herself or worse.

That said, he said he was still shocked by what she posted to her "girls", and said he didn't know what to do next. I told him I am worried about him and his future if he stays with Jessica and goes through with the marriage. He thanked me and hung up. He still sounded pretty shaken. The next day, he asks me to call him so I do that.

He explains to me that everything was okay, and he talked to Jessica about the whole situation. She told him it was just a joke and the kind of thing her friends are used to sending in their messages. Apparently she apologized and said that it was her fault for not making sure I was "on her level" (Harry's words trying to quote Jessica, FWIW).

I'm pretty skeptical of that, though. She seemed serious to me. She also seemed serious when she messaged me privately:

"You are on thin ice."

She also sent another message in the main group chat saying "This is all of y'all's reminder that I need your full support, and any undermining of my and my wedding will have serious consequences." So...that's where things stand. I told Harry that I don't really believe it was a joke, and I believe that Jessica is trying to control him just like she's trying to control her bridesmaids.

He just said that he is in a difficult situation, she is stressed out, and he trusts her. So that's where things stand. Apparently I am still in the darn bridal party. Dress stuff is happing in the next week or two. I really thought Harry would get to his senses but apparently not yet. Now I need to decide what the heck to do next.

The internet was concerned by the update.

Justrennt wrote:

It was not a joke because she threatened you with "You are on thin ice." I would not be surprised, if she isolate him from you after the marriage. Your brother is not believing you, nor he sees the red flags his beloved Jessica is waving. Well, you did your best. I just hope it doesnt take years to find out that she is not the person she pretended to be. It's a sad story.

ALittleBitEnchanted wrote:

Send him the text she sent you, and then insist he sign a prenup. She sounds awful.

OP responded:

I will at some point, but I'm scared if I do that now then she'll just say it's another hilarious joke.

Here4CatVideos wrote:

If it were me I’d bail. Nothing is worth having to deal with a gaslighting manipulative b****. I’d be worried that she’ll try something to hurt or embarrass or turn the whole family against me. I wouldn’t care what the family would think. They all sound horrible anyway. The mom is just as manipulative and brother is a spineless pushover.

He’ll regret this after the wedding, when the wedding high is gone and they’re back to their normal lives and realizes he’s in a one-sided marriage where he doesn’t have much of a life and only does what Jessica wants him to. Book a vacation for the wedding day and just chill and treat yourself to a stress free weekend.

MidianMistress wrote:

Decline. Don't be in the troublemaker's wedding party, only those who support the marriage should be in the party. You know the marriage is going to be a s**tshow, you know that your brother will end up hurt in the end, so don't even pretend to support HER.

Tell your brother, she isn't your sister and you aren't there to support her, you want to support him, if he doesn't want you in his party, I would ask to attend as an invited guest.

Stand up for yourself, she can gaslight him, don't let her do it to you. This is part of a plan of hers to separate him from his family, so tread carefully, or she will win, and your brother will be the one left broken and alone. Make sure you are there for him when it happens, because, it will.

A little over a week later, OP shared another update.

Thanks again for all the support and advice throughout this situation. I'm the girl who is in a messed up situation with my brother who proposed to his really-not-good girlfriend who I know from school. And, until recently, I was a member of her bridal party. Warning that this is dark and mentions s*icide.

So, the update:

I had time at home for spring break, so I finally showed my mom the text messages from Jessica in person, including the insane list of "rules" for the bridal party and her follow up message to me saying I was on "thin ice" after I told my brother.

My mom seriously broke down. She didn't apologize for being mad at me when I wasn't pleased to hear the news from the "happy couple," but at least she doesn't seem to hold it against me. Aside from that though, I am honestly surprised mom took it as seriously as she did--I thought she would say something more like "well, it's his life", instead of butting in.

Anyway, Mom called Harry right away to talk to him. I asked her to put it on speakerphone and she did after a bit. I think that the combination of my own warnings, plus our mom's sheer exasperation at the whole situation finally caused Harry to come to his senses.

He heard what Mom had to say, and in that moment I was able to convince him that Jessica wasn't just joking around with her list of rules (especially with the help of the "thin ice" message). Harry sounded really shaken up and agreed to meet us without bringing Jessica along (phew!). We had dinner at our house and discussed everything.

To him, it sounds like he was more in love with Jessica ~6 months ago than he is today. He said that over the course of more recent time, he's seen Jessica become more and more reliant on his support and he hasn't felt like there's much he can do except cave in to what she wants.

I think that seeing the tone of her communications with people outside the relationship meant him feel like her depression was more of an "act" than a real thing. I'm not a psychologist so I can't say how real that is, but I could believe it. Harry and our mom cried for a while and then came up with a plan for Harry to call off the engagement and begin to move out over the next few days.

He went home and we stayed in close contact for a while. He told us he was feeling ready and did tell her that he needed to reevaluate some things on his own. Apparently, she did not take it well.

Harry stopped responding to us for a day and a half and then called me. Jessica had begun saying that she had nothing to live for except Harry, and that if he abandoned her after all this time then she would have no reason to keep existing. Harry just cried on the phone and said he felt so trapped.

I didn't even know what to tell him. I wish I had told him he needed to forget about Jessica and that she was only playing him, but I don't know if he would believe me anyway. Now Harry hasn't answered any of my calls and is only giving very short and slow answers to texts from our mom and I.

Jessica meanwhile made a Facebook post of a picture of a heart with tears on it saying "If only you knew how much you meant to me, you would never hurt me". Se's also posted a lot of nonsense in the BRILLIANT BRIDAL B*TCHAZZZ group chat and appears to be loving the attention from her friends.

I don't know if she forgot I am in there, or if she wants me to see her messages and thinks it will make me feel guilty or something. I just need to make sure that Harry is okay. To be honest, I don't really care what happens to Jessica.

Sure it would be best for her to get help, but she has caused so much damage in the lives of people I care about and I doubt she'll ever stop. Like honestly f#$k her, I just want my brother back.

Sorry I'm writing this post all gloomily so far...to be honest, I think things will be okay. Harry and our mom both know that he needs to end it with Jessica, and now Harry just needs to make that happen. Then we can all laugh together about Jessica's BMI tracking strategy and minimum bridesmaid spend requirement :)

The internet was quick to respond.

No-Background-6199 wrote:

Hopefully Jessica gets the help she needs. And your brother gets the space to clear his head and decide what is best for him. Based on updates and post he needs space away from her.

OP responded:

Thank you <3

I wish he had just stayed with us longer and gotten more time away from her

ferrets-are-awesome wrote:

I highly recommend a welfare check be called in since you know she was threatening s*icide.

Dachshundmom5 wrote:

If she's making threats to her life, he needs to call the p*lice and report it. Then, notify her friends/family. If she's sincere, she needs more help than he could ever give. If she's attention seeking, it gives him time to get his things and get out. Either way, he needs to remove himself as the object she's fixating on.

It's a tactic of ab#sers to threaten self-harm to maintain control. Until he accepts that he can't "fix" her, he is trapped.

The concern needs to extend that she isn't bluffing and might try to take him with her.

Intelligent-Ad-4568 wrote:

Jessica had begun saying that she had nothing to live for except Harry, and that if he abandoned her after all this time then she would have no reason to keep existing.

"When someone does this believe them. Okay, you are saying if I leave you will h*rt yourself? It that what your telling me? Yes. Okay, I'm calling for an ambulance."

Its an manipulative tactic, but it also could be true. So believe them, get them help and call their family to meet them at the hospital. And leave. If your brother calls you and tells you he can't leave or doesn't feel safe because she is threatening self harm. Believe. Call the authorities, call her family and get her the help she needs and then leave.

Electronic_Goose3894 wrote:

Honestly, at this point after reading everything that's going on. I'd just send a message to your brother reaffirming that you love him, but you're done. That he'll always have a place with you if he needs it, but you're not going to watch him tailspin into misery.

Because the thing is, he's not okay in any capacity but he's already decided that being in a manipulative and loveless marriage isn't a deal breaker for him because as you said yourself, he's well aware of who and what she is so you aren't going to change his mind, nobody will until he decides to do it himself.

This is beyond stressful, hopefully Harry fully steps away and saves his own future.