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Widower Furious After His Judgmental Sister Tells Their Mom He’s Pursuing A Relationship With His 8-Year-Old Son’s Teacher

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Dating when you already have children can be hard, but it’s especially hard when a well-meaning friend or family member gets in the way.

One Redditor “Equal_Fruit” is a widower who recently asked his eight-year-old son’s school teacher out on a date. His sister didn’t like the idea and told their mother, which he vented about on the “Am I the A**hole?” (AITA) subReddit.

The Redditor asked the thread: 

“[Am I the a**hole] for losing my s**t on my sister for telling our mother about my personal life?”

He explained first how he and the teacher became close.

“I’m a widower with an 8-year-old son.”

“His teacher is new in our town (she only arrived last September) and lives in our block, we’re practically next-door neighbors. Like, if we’re out on our balconies we can see each other and talk.”

“She obviously knew no one here, so over these past few months and especially during the lockdown, we grew kinda close.”

“We had a bit of a moment the other day, I asked her out, she said yes. But we both decided to wait until the school year was over.”

He shared the news with his sister, who did not react the way he was expecting. 

“I called my sister to tell her and she called me an a**.”

“She said that I shouldn’t be doing that to my son, because it’s not uncommon for boys his age to develop crushes to their teacher and that I don’t want to make things complicated for him.”

When he didn’t agree with her logic, his sister became more persistent.

“I told her that she doesn’t know what she’s talking about cause I was sure my son couldn’t care less since he already has a crush on a classmate of his. And also I wasn’t asking for her advice, I was just calling her with some good news.”

“She doubled down and told me that I was being irresponsible because 8-year-olds can be very fickle and get 3 different crushes in one week, so I shouldn’t count on him not becoming jealous of me.”

Then the sister changed tactics. 

“I told her that that was it with this discussion and I’d hear no more. If his teacher thought there’d be no problem, then there was no problem.”

“She apparently thought that wasn’t a good enough point either, cause since isn’t the most experienced teacher (she’s 25 and has only been working for a couple of years).”

“And then [she] started saying how she’s too young for me anyway (I’m 35) and that I always try to date younger and that maybe it’s time to look for women my age.”

Upset, he ended the call. 

“She wasn’t as aggressive with that last remark, but it still stung and I was already a bit riled up from what she had said previously, so I just told her that I had enough and hung up before I lost my temper.”

But that wasn’t the last phone call he received that day. 

“2 hours later, my mum called me and started saying the same things, parroting my sister. I tried to calm her down and promised that I’d be extra careful and that’d I’d break up at the first sign of trouble.”

Needless to say, he was furious. 

“But then I immediately called my sister and… yeah, it wasn’t pretty. I told her that she should have never involved our mother in this and that the last thing I wanted was to have her following my disappointing love life so closely.”

“I may or may not have called her various names, but I felt that she had no right to do that and it was a huge breach of trust.”

His fellow Redditors wrote in anonymously, commenting on the OP’s (Original Poster’s) story using the following scale:

  • NTA: “Not the A**hole”
  • YTA: “You’re the A**hole”
  • ESH: “Everybody Sucks Here”
  • NAH: “No A**holes Here”

Though the conversation did not focus particularly on the rating scale, there were questions about the sister’s logic.

One Redditor pointed out that, though she may be trying to help, the sister’s mentality around entitlement could be dangerous.

“I also have a question, why were you not already angry when she started spouting off that pretty much guano psychotic bullshit and ridiculous arguments?”

“I also would like to offer some advice on that potential development. If your son develops a crush on your partner in the future and get jealous of you then you deal with that then, same thing if he develops a crush on anyone else and get jealous at someone.”

“You don’t reinforce that kind of entitlement to other people, which is exactly what your sister is advising you to do. If you back off like your sister wants you would be teaching him that he is entitled to other people regardless of what they or their partner wants and that’s frankly both toxic and dangerous.”

“That would be teaching him that women are things that he is entitled to if he wants it and no one else is allowed to “steal” those things “from him”. This is incredibly troubling to be honest and bigger issue imo.”

“Also NTA.”GaiasDotter

A couple Redditors also pointed out how hard this could be on the son if the relationship didn’t work out.

“I think the only concern I’d have on dating a teacher is a) to wait until the kid isn’t in her class so nobody can accuse her of favoritism, b) make sure she knows if her school has its own policy first, c) see what the school environment is when it comes to gossip. If she’s 25 and a new teacher she may not have experience yet dealing with a gossip-y PTA, judgmental colleagues, etc.”

“It’s normal stuff that happens in a lot of fields and doesn’t necessarily have to be a deal breaker on dating altogether, but it may influence how fast or slow you want to become public or share with your neighbors.”

“I had a fairly young/new colleague about 25 do some serious damage to her reputation at my last company because she got romantically involved with a coworker. It’s definitely a ‘proceed with caution’ scenario.”

“As for the age gap… ‘there’s no normal life, just life.'”kelli-leigh-o

“Legitimately the issue is that the 8 yo simply has a relationship with the teacher so it’s more likely that he would get attached to her as a mother figure. And if it doesn’t work out, it would be hard on him.”

“But it seems like the OP would be aware of that and would try to keep things separate until they potentially got more serious.”

“I strongly believe that young children should be distanced from their single parents romantic lives simply because my own divorced parents didn’t do it and it was really hard on me and my sister. But I really do think the OP is aware of that.”


Others figured she had more issues with the age difference and simply mentioned crushes first.

“Notice how she gave that nonsense explanation of the son possibly getting a crush on the teacher and harped on that for a while before going oh by the way you also shouldn’t be dating women that much younger than you? Yeah, my money says that the whole student-teacher thing doesn’t bug her at all, and her actual issue was with him dating younger women.”Dan-D-Lyon

“She probably disapproved more of the age gap, and the fact that she is your kid’s teacher and had to come up with a quick reason that wasn’t outright calling you generally inappropriate. There needs to be more background info to condemn her, like what your history is of dating people a whole decade younger than you or something.”fullmoonpig

One Redditor offered a unique perspective on the issue with the age gap. 

“If the age gap is the real issue with your sister then I think you both have to sit down, talk, and really listen.”

“I’m in that age range and as mature as I’d like to think I am, in all honesty dating a widower in his mid thirties with a kid that’ll be in his teens in the blink of an eye is a big deal and probably more than I could handle.”

“Dating and having fun is one thing, but when feelings become real and attachments form it can be a lot to expect someone to become a de facto parent in their mid 20s. Even if you don’t think that you are pressuring the person or don’t expect them to do anything, in that situation they will feel like they have to step up as an obligation because ‘they [should] have known what they were getting themselves into’.”

“Mid 20s is mature, but all that this situation entails is a lot to handle. From a maturity standpoint I hate to admit it, but our brains are still on the tail end of fully developing.”

“Closer to your age would probably be better suited to dealing with this, especially if you became a widower when your child was very young. There’s a lot of grief that has to be hidden and avoided and selflessness that goes into being an active single parent will still dealing with your own grief.”

“Idk if I’m making sense. If what I’m think is what’s going on, I think neither of you are the A. You just need an honest dialogue. She might be worried about you and not know how to express it in a healthy way.”

“Sorry for the rambling, and best of luck!”DancingInAHotTub

It was surely frustrating to suddenly have his mother involved in the conversation, but hopefully the sister had the best intentions.

Written by McKenzie Lynn Tozan

McKenzie Lynn Tozan has been a part of the George Takei family since 2019 when she wrote some of her favorite early pieces: Sesame Street introducing its first character who lived in foster care and Bruce Willis delivering a not-so-Die-Hard opening pitch at a Phillies game. She's gone on to write nearly 3,000 viral and trending stories for George Takei, Comic Sands, Percolately, and ÜberFacts. With an unstoppable love for the written word, she's also an avid reader, poet, and indie novelist.