If there’s one thing we can all agree on about dating applications, it’s that they largely centre around superficiality. If you’re blessed with a chiseled jaw line or a flat stomach, then good for you. But for the rest of us who are mediocre at best, Tinder isn’t exactly our best playing field. Being generous with your right swipes yet not receiving any matches in return (the struggle is real…) can really suck!
A twist to the whole realm of online dating – Would You Rather questions.
Thankfully, Letterbox’s founders, Sebastian Quek, Ian Ngiaw, Xu Bili and Lei Mingyu, recognised this sad reality that many of us face. Geniuses as they are, the four School of Computing students decided to add a twist to the whole realm of online dating – Would You Rather questions.
Letterbox isn’t your regular dating application. Unlike the usual swiping, you send “letters” consisting of answers to Would You Rather questions instead. In that way, you can access someone’s thought processes and personality before deciding if you want to match.

The questions are a brilliant concept. I’m slightly embarrassed to admit this, but I spent way too much time choosing my answers because they were just too thought-provoking. We all know how difficult it can be to start a conversation with someone. Yes, even online! But when you know that he or she would rather live without elbows than knees, there really isn’t need to scratch your head over a conversation starter anymore.
So last week, I caught up with Sebastian and Ian. It was pretty interesting getting to know these tech whizzes and digging into the behind-the-scenes of NUS’ favourite dating application. And of course, no interview is complete without asking them some of their own (half intriguing, half morbid) Would You Rather questions.

First and foremost, how did Letterbox come about?
Sebastian: Letterbox was actually an assignment for one of our projects last semester. We had to create a mobile application and submit it to the SOC Term Project Showcase (STePS) – School of Computing’s bi-annual exhibition where students get to showcase their projects.
The assignment required us to solve a problem with a mobile application. With help from Professor Ben Leong, we decided to focus on the issue of online dating, particularly in the context of NUS. Prof. Leong also helped us to share it with his network of friends, especially the NUS alumnus, so eventually there’s quite a broad age range within our 1000 plus users. Like what he said, “You don’t really know you need a dating app until you’ve graduated and your social circle shrinks.”
How does Letterbox differentiate itself from other dating applications like Tinder?
Ian: Most dating applications in the market emphasises on appearances. But when you want to talk to someone, you would want to find out more about their personality. So we thought Would You Rather questions would be an interesting way to do that.

How did you guys come up with the Would You Rather questions?
Ian: We stole them.
Sebastian: We are resourceful. (Laughs) We browsed reddit, looked through online sources and different websites. Some of the questions we chose are funny, while some of them are more emotional.

How did you get people to start using Letterbox?
Ian: One of our marketing efforts were the use of posters. We pasted posters everywhere – on top of water coolers, on our friends’ lockers. There’s one right over there. (Points to a wall nearby) We kinda did them “illegally”. Before we officially launched Letterbox, we also went to UTown to ask people Would You Rather questions. We filmed them and shared it on our Facebook page to gain some publicity. Then, we officially launched Letterbox during STePS, and our team won first place!
Sebastian: We did face extreme growth in users thanks to NUSWhispers. NUSWhispers has a pretty active group of users, so shedding some exposure of Letterbox on it did help us with publicity.
Is this by far your most memorable, or favourite, or best-faring project?
Ian: All of the above!
Sebastian: Definitely.
What is a good dating bio users should put up?
Sebastian: You definitely need a profile picture. We’ve actually seen users without a profile picture! Then there are also people who simply leave the Facebook silhouette as it is. As for the bio description, I don’t think it plays a huge part.
Ian: We did make a mistake though. When Letterbox first launched, we had “I like cats” as the default bio description. And now there are a lot of users who used it as their description. So currently there are a lot of people who like cats…

What was the biggest challenge your team faced in the making of the app?
Sebastian: The technical aspects were challenging. We wanted to target a large population of users but everyone’s using a different mobile software. We only had the Android version of Letterbox initially. We managed to launch the iOS version sometime later.
Ian: We faced some challenges in the marketing of Letterbox too. Among all the STePS teams, we were the only ones with a full-team of computing students. Many of them had Business or FASS students and because of this, it took a lot of extra effort when it comes to publicity. I would say this module took me a lot more effort than all of my other semesters’ modules combined!
What are some of you personal favourite applications?
Both: Telegram!
Sebastian: It’s fast, you can use in on web, you can send GIFs…
Ian: We can send each other monospace text* on Telegram as well. It’s a really useful tool when we want to send each other computing stuff.
*Monospace text is a font type whose letters and characters each occupy the same amount of horizontal space i.e something we non-tech people will never use.

What’s the best online dating advice you can give someone?
Ian: Don’t be weird. Don’t be creepy. Don’t be annoying and you’ll be fine.
Sebastian: Show interest. In Letterbox’s case, when you have a match, don’t just leave it hanging. Start a conversation!
What is the direction of Letterbox?
Sebastian: Our team is pretty busy currently. Two of our members are overseas, and Ian and I are busy with other stuff. It’s hard to find the time to work on updates and improvements. To be honest, we haven’t been publicising Letterbox since we first launched it. There are still many active users and new users though.
And here’s my favourite WYR question from Letterbox: Would you rather pee every time you stand, or poop every time you sit?
Sebastian: Would it be a continuous stream or flow?
Ian: I would rather pee every time I stand. You can wear a diaper and peeing in a diaper probably wouldn’t be as obvious pooping in one.
Ian: Hmmm… I would rather pee as well. Yeah you can contain it easily. And pee isn’t as smelly!
If you’re still looking for a date for Valentine’s Day, why not give Letterbox a try?
Have you tried Letterbox before and met your match? Tell us your story on Facebook or in the comments below!

