May 28, 2026 at 6:15 pm

The Boarding School Trap: Why a Father’s Elite Ambitions for His Son Triggered an Unresolved Marriage Crisis

by Michael Levanduski

Parents in disagreement

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All good parents want what is best for their children, but sometimes it is hard to figure out exactly what that is. There are many situations where there are multiple good options, but you have to choose only one.

What would you do if it was coming up on time to pick what high school to send your son to, and you wanted to send him to a boarding school like you went to, while your wife wants to keep him close to home at a normal school?

That is the situation that the couple in this story is in, and they are having a hard time coming to an agreement. There are obvious pros and cons to both options, but the father says that this boarding school will give him a major advantage when it comes to getting into top universities.

In many ways, it is these conflicts in life that are the most difficult to overcome. There is no doubt that both parents want what is best for their child, and both have strong and valid arguments for their desire. At the end of the day, they just need to come together and pick one and live with the decision. Read on to see all the details that are making this such a hard choice.

AITA for wanting to send my son to boarding school?

So I [41] want to send my son [11M] to boarding school for high school, and my wife [39F] is super against it.

Boarding schools can provide a wonderful education. Of course, being away from friends and family can also be very hard.

So, what’s happened is, I am trying to send my son to a top boarding school in New England (Andover/Exeter/Deerfield/Hotchkiss/Groton/etc).

I personally went to one of those schools, and I’ve seen first hand the resources and connections they have to offer.

There is no doubt that these schools can set kids up for a great future.

They’re also top feeder schools to top colleges. I messed around too much in high school and ended up at Tufts (a great uni, but still) where as my wife went to a top school (Harvard/Yale/Princeton). She went to a standard high school though.

She and I both agree that we want our son to go to a top college, but our methods are very different. I prefer a more hands on approach vs her more hands off approach.

I doubt anyone would argue that these schools aren’t a wonderful opportunity.

Now, you’d be kidding yourself if you acted like those high schools didn’t provide a significant advantage in the process.

I want to position my son now to be ready to have the best shot of admissions (basically tutors and counselors and the sort) whereas my wife thinks that’s too much for someone his age, and that it’s okay if he doesn’t get in.

Of course not, but neither is his wife.

So, basically, am I really out of line for wanting what’s best for my son?

AITA?

This is one of those difficult situations where nobody is doing anything wrong. It is obvious that a boarding school can provide their son with a significant head start toward his future. On the other hand, it is equally obvious that sending a child off to school is very difficult on everyone, and many kids do great at a normal school.

At the end of the day, this Mom and Dad, along with input from their child, need to come to an agreement and make the best of it.

If you enjoyed this story, check out this post about a woman who restored a vintage camera with her own money and doesn’t want to hand it over to family.

Let’s see what the people in the comments have to say about this difficult story.

Here is someone who says Dad is framing the two sides of this issue unfairly. I don’t think I disagree with him.

Comment 1 117 The Boarding School Trap: Why a Father’s Elite Ambitions for His Son Triggered an Unresolved Marriage Crisis

It is possible that they could find some type of middle ground.

Comment 2 117 The Boarding School Trap: Why a Father’s Elite Ambitions for His Son Triggered an Unresolved Marriage Crisis

This commenter thinks that he is too concerned about this too soon.

Comment 3 116 The Boarding School Trap: Why a Father’s Elite Ambitions for His Son Triggered an Unresolved Marriage Crisis

I think this commenter is looking at it wrong. Both parents just want what is best.

Comment 4 115 The Boarding School Trap: Why a Father’s Elite Ambitions for His Son Triggered an Unresolved Marriage Crisis

This commenter is half right. The child would be a legacy since his mother went to an Ivy League.

Comment 5 112 The Boarding School Trap: Why a Father’s Elite Ambitions for His Son Triggered an Unresolved Marriage Crisis

When it comes to parenting, few disagreements are harder to overcome than those where both parents are right. This couple needs to find a way to get on the same page. At the end of the day, one parent will have to give in and let the other have their way.

While this can certainly be difficult, it doesn’t have to cause conflict. Whichever school they decide on, both parents need to come together to help their child thrive. One other thing to consider is that this will impact their child more than anyone else. They should get his input too.