Dating Elite School Boys

Many of us girls dream of a romantic, chivalrous guy who will sweep us off our feet. And many believe there’s no better place to find such men than in elite all-boys schools.

These institutions pride themselves on turning boys into gentlemen and producing future doctors/lawyers/insert-high-salary-jobs-here that our mothers would love us to date.

But how far can we believe elite schools are mass-producing perfect men? These 9 Singaporean girls who’ve dated guys from all-boys schools spill the tea and share with us the good, the bad and the ugly.

Names were changed to protect identities.

1. “Boys’ school boys are more gentlemanly and take care of you better.”

Most of the guys I’ve dated came from all-boys schools. As compared to guys from mixed schools, I find them more gentlemanly.

They’d hold doors open, make sure I walk on the inside of the road and drop a “Thanks for the nice dinner” text after a date more often than guys from mixed schools.

Once, when I had just started dating my current boyfriend, I got drunk at a classmate’s birthday party and was afraid my parents would find out.

So my boyfriend booked us an Uber to his place and tucked me into his bed. The next morning, I woke up and found him sleeping on the sofa.
Sarah, 19

2. “They’re too elitist to associate with others.”

My ex-boyfriend was from an elite all-boys school whereas I was from a neighbourhood school. When we got together in JC, it felt like a Romeo and Juliet love story because we came from such different backgrounds.

When our relationship became more serious, I tried introducing him to my friends. But he always turned me down. Confused, I questioned him and he admitted he’d rather not talk to people from ITE or Poly because they “weren’t on the same intellectual wavelength”.

No wonder he never introduced me to his friends the entire two years we dated. He was ashamed of my ‘inferior’ neighbourhood school background as it was ‘beneath him’ to be associated with people like me.

Needless to say, we broke up shortly after.
Rachel, 20

3. “Boys’ school boys make you feel more cherished.”

At 16, I dated my first love who was the most supportive and adoring boyfriend I’ve ever had. He was always there to listen, whether it involved a text about scoring well on an exam or a rant about a tiring day.

He’d remember the little things like my Subway order and surprise me by buying me things I’d casually mentioned I liked. He was generous with compliments, but also completely real and honest with me.

I feel like boys’ school boys put in more effort to make you feel special because they know better than to take a girl for granted once they’ve got her.
Marissa, 24

4. “They’re more insensitive.”

When I was in J1, I thought I snagged a good guy. He was from a well-to-do family and would treat me kindly and with respect.

However, he had a hard time recognising his own privilege. When I didn’t get an overseas scholarship, he couldn’t understand why I was so upset. He thought getting my parents to pay for the expensive tuition was no big deal.

He’d also often criticise his classmates’ grades when they scored poorly on tests, saying they should’ve bought more private tuition.

Hanging around him became frustrating as I had to keep explaining to him why his comments were insensitive. It wasn’t his fault he wasn’t ‘woke’—he was just raised too sheltered to understand what others were going through.
Jennifer, 20

Also read:

Why My All-Girls School Education Was The Best Thing That Happened To Me

5. “Boys’ school boys are all talk, no action.”

I had a classmate who made a name for himself as an F-boy, and was always boasting about his sexual conquests. In J2, he took an interest in me and repeatedly asked me to hook up with him.

When I finally agreed, he did a 180 and changed his mind. He even told people in school I was the one who creepily came onto him and that it made him uncomfortable.

Turns out, I wasn’t the only one among my friends who encountered such guys. It made me realise that a lot of these elite school F-boys are bluffs. They can hit on girls as much as they want, but at the end of the day, they don’t have the balls to follow through with their actions.
Rachelle, 20

6. “They become jerks when they’re with their clique.”

I’ve been dating my boyfriend since we were 17. When he’s with me, he’s sweet and respectful, but with his rugby bros, he becomes the biggest asshole. They’d spend breaks sitting in the canteen, making degrading jokes about the girls who walk past.

Even though I knew about his gross behaviour, I thought he’d respect me enough to never speak about me that way. But when I found out he’d been discussing my ‘awkward’ performance in bed with his teammates, I was shocked, disgusted and humiliated.

I’m still dating him but I really wish he’d change. He’s a great person when he’s on his own, but the whole toxic ‘banter’ culture he grew up with just seems too ingrained to erase.
Bethany, 21

7. “They’re better conversationalists and more intelligent.”

I’m on dating apps a lot and I find I’m usually more attracted to guys who come from all-boys schools because of how they carry a conversation.

Of all the first dates I’ve had, dates with boys’ school boys always go well. They have a way with words, which they demonstrate through their wicked sense of humour and ability to sweet talk.

The conversation never gets boring because they can talk about everything from the latest memes to local politics. Through chit-chatting, their intelligence shows and I find it incredibly sexy.
Amanda, 24

8. “They’re fake nice guys.”

My OG mate kept pestering me to go out with him since the beginning of orientation, insisting he wanted to get to know me better. But when he failed to turn my consistent “no”s into a “yes”, he told the whole school I was a “cold-hearted bitch”.

Sadly, my school was full of boys’ school guys like him, and they accepted it without question. It bothers me how these guys thought it was normal to come up with lies to ‘explain’ why a girl wouldn’t go out with them.

It just goes to show they’re not as nice as they think.
Tanya, 19

9. “They don’t prioritise you.”

When I entered one of the top five JCs, I knew it’d be a norm to prioritise academics over romantic relationships. But what I didn’t expect was how I’d be a victim of ‘breakup season’.

Whenever exams rolled around, my ex-boyfriend would dump me to focus on studying for exams and ask me to take him back once the exam period was through.

It’s understandable if a guy has trouble juggling studies and other priorities, but it bothers me how these guys saw relationships as insignificant and disposable.
Sharon, 18

Don’t Judge A Book By Its Cover

While some of these all-boys school stereotypes may be true, it’s important to remember everyone is different and every relationship has its own obstacles. In the end, what matters is you understand who he really is, not what you’ve been led to believe.

This post was first published on 21 March 2018 and last updated on 26 September 2023.
Cover image: Source

Also read:

Shit Boys Say To Girls When Growing Up In Mixed Schools In Singapore