Will They, Won’t They? Exploring Relationships Evolving From Friendships

CHIN NGIOK SHUAN dives deeper into friendships to explore the potential of best friends turning into lovers.

Emily Deschanel (left) and David Boreanaz (right) as Temperance Brennan and Seeley Booth respectively in the Bones series that ran from 2005 – 2017. Brennan and Booth are the main couple of the show. Photo taken from Patrick McElhenney, FOX.



Ngiok Shuan Chin Sub-editor
Hype Issue #55

Published on
May 20, 2022

“Do you like him?” and “When are you two going to get together?” are common questions I’ve gotten from my friends when I tell them about my male best friends. Back then, I’d usually brush the questions off with a laugh, telling them that it was impossible and that we’d never cross the fine line between friendship and relationship.

It was only when I first recognised the crush I had on my first male best friend, did I realise that maybe my friends were onto something. 

(Spoiler alert, it went nowhere. I confessed when I was 13, and he told me he didn’t like me in a romantic sense before adding he had a crush on another one of his close friends. We’re still good friends, and we laugh about it occasionally – but that definitely did hurt 13-year-old me.) 

But just imagine knowing someone like the back of your hand – all their likes, dislikes, worst fears and most embarrassing stories. Picture you two sharing your deepest, darkest secrets with just one another and only ever talking to that one special person – because you both are just that close.

Try taking that a step further. 

Admittedly, the friends-to-lovers trope, be it in books, movies or television shows, has always been one of my favourites. Something about someone knowing you inside-out, embracing all your flaws and imperfections and still loving you through everything just gets to me. 

Television show characters Cory Matthews and Topanga Lawrence from Boy Meets World, Seeley Booth and Temperance Brennan from Bones and book characters Bree and Nathan from The Cheat Sheet are a few of my favourite fictional couples who started off as best friends before they became partners. They make the transition from friends to lovers look so easy, that you can’t help but wonder if you would end up in their shoes one day.

Ben Savage (right) and Danielle Fishel (left) as Cory Matthews and Topanga Lawrence respectively in the Boy Meets World series which ran from 1993-2000. Matthews and Lawrence were best friends who got together in the second season of the show, and continued to play supporting roles in the Disney spin-off Girl Meets World. Gif taken from WiffleGif.

With all that said, while some believe that best friends commonly fall for each other at a point in their friendship, in reality, only a few will act on their emotions and confess. If they’re lucky, the other party reciprocates their feelings and they get together. If not, a few pairs manage to maintain their original friendship. In the worst case scenario, they stop being friends completely. 

But why do best friends fall for each other? What can be some pros and cons of dating your best friend, and is it a smart decision to enter a relationship with them?

Why do best friends fall for each other?

“It is expected that some see the natural progression for their relationship to turn from friends into partners,” Max Chai, 19, says. “As you spend the days, months and years with your best friend, the precious memories that the two of you share will definitely encourage some to want to make even more intimate memories with their best friend, leading them to enter a relationship and taking the next step to spend even more time together.”


In an interview with WHYY, Paul Eastwick, a researcher at University of California, said that most romantic relations tend to form within friend groups, and these couples usually start dating after about a year of being friends. 

If this is possible between friends, what does this mean for best friends? Subjectively, best friends tend to spend more time together than ordinary friends, and this would cultivate a deeper understanding of each other as compared to the understanding ordinary friends have.

Not only that, most friendships would have already endured some hard times. I’ve had fights with my friends over a multitude of issues – whether they should stay with their partners, whether they should fly overseas to meet their favourite celebrity during school terms, et cetera. While most of the fights weren’t pretty, we did manage to work through the issue together and come out stronger than before.  

An article by Love Life Links says the friendships that have undergone certain troubles make both parties consistent and steady counterparts for each other, thus, it wouldn’t be difficult for them to stick together throughout future problems. 

As with friendships, relationships also stem from common interests, which makes it easy for them to get along when they have various interests to discuss. The more common interests there are, the more they are able to converse with each other, making it easier for them to forge deeper bonds. 

“When friends have common interests, they spend a lot of time talking about these interests. The more they talk, the more they learn about each other as well. When this happens and they become closer, feelings develop eventually,” says Heng Jingwen, 17.

Are there pros and cons of dating my best friend?

While some may see more pros than cons or vice versa, there are various reasons as to why a number of best friends make the transition to becoming a couple. What some see as benefits might be seen as a risk to others. To me, it depends on how willing you are to throw caution to the wind. 

There could be more pros and cons that I didn’t think of, but these are some of the more important ones I would personally weigh before making a decision about getting into a relationship with my best friend. 

Pro: You two are already familiar with each other

The familiarity that you feel as friends can ease the process, since you already know how intimate both of you are with each other.  

From the bad habits to the little quirks, you tend to pick up on the little things your best friend does that others may never notice. There’s an unparalleled level of trust and comfort between the two of you, and with shared interests and experiences, there is no need to learn how to connect with them when you already know how well you get along with each other. 

“I think it’s because best friends spend a lot of time together that they know so much about each other and accept each other for who they truly are. That’s why they fall in love, because they see so many sides of each other that others may not see,” says Ms Valerie Tang, 22, a student at Nanyang Technological University.

That’s why they fall in love, because they see so many sides of each other that others may not see.

- Ms Valerie Tang, 22

Student at Nanyang Technological University


“As best friends, you are already intimately familiar with each other, their likes, dislikes and so on. You know what your partner would love most from the get go, and what to avoid doing to get on their nerves,” Max says. “A relationship born [out of being] … best friends is bound to be easy initially, with the months and years of communication you’ve had with each other.  Becoming partners also means that you would be able to spend even more time with the person who you most likely already enjoy and spend a majority of your social life with.”

Pro: Both of you are more willing to work through your problems 

When problems arise during the relationship, it’s the emotional investment you and your best friend have in each other that would make you want to work together to overcome the problem instead of working against each other.

With both of you knowing how important you are to the other, you are less likely to give up on solving the problem when you know that you have already worked through other issues with them by your side.

Since both parties know how the other functions, such as what ticks the other off or calms the other down, you can compromise to find the solution that you two need and work towards it together. 



Emily Deschanel (left) and David Boreanaz (right) as Temperance Brennan and Seeley Booth respectively in the Bones series that ran from 2005 – 2017. After an argument revolving around another man’s confession to Brennan, both of them talked it out during a car ride.  Gif taken from GIPHY.

“Your best friend is your partner, the one who has been there every time you feel down. Since best friends already know each other so well, they can always be there for each other through thick and thin,” says Jingwen.

Con: You might be risking more than your relationship with your best friend

It’s normal that when you enter a relationship, you enter it with preconceived notions of what you want from your partner. Maybe you expect flowers before every date, or fancy dates at expensive restaurants that are bound to make your other friends jealous. These things are far from what you and your best friend are used to because neither one of you have ever done or experienced it before.


However, it’s these newfound expectations that you have for your new partner that may cause strains, especially if both parties are not on the same page about these new expectations.

“With relationships, come expectations for your partner, and that’s where things get messy,” Max says. When prompted about what expectations he meant, he said, “The things that I might’ve done as their best friend, such as me forgetting their birthdays or being late to our meetups, they might have laughed and made a joke over in the past. But after getting together with them, these habits may turn into annoyances because of the new expectations, and that drives a wedge into our relationship.”

Should the relationship end on a sour note, the original friendship might die out as well due to the awkwardness both sides may feel.

In an article written by Joy Youell for betterhelp, she says that the hurt from a broken relationship with your best friend can cause distance between the two of you, which leads to the friendship falling apart. 

(I can confirm. My first boyfriend was one of the best friends I ever had, and breaking up with him lost me my confidante. We still talk every now and then, but we’ll never be as close as we were back then.) 

“If the relationship doesn’t work out, there’s a chance of losing your best friend forever and that it will be harder to find another relationship like the one between you and your best friend in the future,” Jingwen says.

Con: Your friend group may end up splitting

This is another big risk that could put others off the idea of getting together with their best friend. 

It might not be too far-fetched to assume that best friends tend to run within the same friend groups. If everyone gets along well, there’s no new blood that might upset the delicate balance with the whole group. There’s also no need for anyone to get used to any awkwardness there might be from adding a stranger into the mix. 

But what happens when a fight occurs?

When arguments happen, it’s common that we seek the support of our friends to back us up, which can prove dangerous when everyone belongs to the same friend group. 

An article written by Livelif suggests that when this happens, it can cause tensions and strain relations between not only the couple, but others in the friend group as they see the others taking the side of the other, who, in their perspective, is currently in the wrong. 

If tensions run too high and someone snaps, it’s not hard to break a delicate relationship with careless words and actions. If that happens, the damage caused might be irreversible. 

Not only do you run the risk of losing your best friend and partner-in-crime, you also put your other friendships on the line when you get together with your best friend. 

“Having the same friend group does make it easier most of the time, but sometimes, when tempers flare and people start losing their cool, a lot of ties could break.” Ms Tang says. 

Should I or should I not enter a relationship with my best friend?


Singers Camila Cabello (right) and Shawn Mendes (left) performing at the 2019 MTV Video Music Awards in 2019. They were confirmed to be dating in 2019, but had broken up by 2021. The two have called each other their best friends since their first collaboration on I Know What You Did Last Summer in 2015. Screenshot taken from YouTube.

Personally, I would still date my best friend. A friend of mine always told me that when it comes to relationships,  if I’m going to fall in love, it should be with my best friend, since it’s not everyday that we find someone who knows and accepts every part of us. It’s even rarer to find someone who will love us through everything we’ve been through. 

I would rather take the risk of everything changing, no matter for better or worse, than to not take a leap of faith only to find out I stood a chance.

But understandably, not everyone would view the situation similarly. I’ve seen couples who’ve started off as best friends thrive in their relationships, their bond with each other only strengthening with time. 

However, I’ve also seen other couples fall apart when certain habits from their friendship turn from endearing to annoying, and what could’ve once been overlooked turn into deal-breakers that tear apart both the friendship and the relationship. 

Depending on how mature both parties can be, even if the romantic relationship doesn’t work out, the platonic friendship could still remain. 

Ms Tang says that while a broken relationship with your best friend might hurt, it doesn’t mean that it was all for naught. 

“The memories you get while being in a relationship with [your best friend] are different from [those you would have had] if you were just friends,” Ms Tang says. “I think it’ll be really beautiful, the memories you get while being in a relationship with that person.”