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15 Awkward Social Dilemmas you would have, or had with your friends

Awkward situations! Social dilemmas! We face them everyday. Afterall, no group of friends have ever been through 0 awkward moments or frustrations, and in the end we all learn how to deal with them anyway. Here’s our top 15 list of social dilemmas everyone would have probably faced, or will face, with long term friends or loved ones

1. The Punctuality Dilemma

“Oh hey Jack, I’m on my way there, just give me 20 more minutes.”

So you have already arrived at your MRT station, and your friend(s) is apparently LATE. And you know, because its your friend, its forgiveable, maybe once or twice. What if they are perpetually late? You start to ask yourself whether you should confront them about the matter. Then again, you also realize that sometimes you are the one that’s late on certain occasions, so you just lost your only moral high ground to scold your latecoming friends. Bummer!

2. The Sacrificing Dilemma

You are trying to organize a big outing with your friends, but of course, not EVERYONE can make it on the same date and time, because different people have different commitments, right? If I put it on Saturday night, 2 people cannot make it. If I put it on Sunday night, 3 people cannot make it. Logically I must put it on Saturday night because more people can make it! So what happens if on both nights, the same number of people (2) cannot make it? The organizer is forced to make a decision on which day to go out. Whatever decision it is, it will be bound to upset those who are “sacrificed” on that date. Damn, those sacrificed friends will start to wonder how come you chose the other date for the other 2 people, instead of them. Then they start drawing conclusions that you probably like that other group better than them. Ugh!

This dilemma is even more worse, when 2 super-fun friends are unable to make it on Day 1, but 3 quiet, introverted friends are unable to make it on Day 2, and a part of you itches to put it on Day 2, because you know that asking the 2 fun friends to come along will make the outing a whole lot more fun. Damn! Those 3 quieter friends will really question how come you chose 2 over 3. Gawd! No one likes this dilemma

3. The Domino Effect Dilemma

This happens the most while someone is trying to organize an outing. Oh yea! Seems like everyone is gonna show up for a weekly gathering at Orchard Road. What’s this? Someone just texted in the whatsapp chat that they are unable to make it. The total headcount drops from 8 to 7. Five minutes later, someone else also took this chance to say they couldn’t make it. Another five minutes later, someone else flies the aeroplane yet again. At the moment, the organizer, which is probably you, starts feeling stressed because only 5 people are left going. As for the remaining 4 people, they start to feel that this outing is not gonna be as epic as planned, because the numbers don’t make up, or the “fun” people aren’t showing up, so they start to think its not worth it and tell the organizer that they don’t wanna go anymore. Headcount drops to 4, 3, and….. because it’s awkward with only 3 or 2 people left, outing cancelled.

Trust me, the organizer will be raging at this point. Domino effect.

4. The Story Telling Dilemma

Your enthusiastic friend decides to tell you a “funny” or “epic” story that happened to them last week. The problem is you already heard it. But they seem so overly excited to tell you the story (they probably forgot they already did) that you just have to suck it up and listen to it again so you don’t hurt their feelings. At this point in time you wonder whether you should spoil the conversation by saying “Oh you already said this last week”, followed by an awkward break in the conversation, or just play along and give a fake laugh “Oh hahahah that’s hilarious!”

Or, even if you haven’t heard the story before, it’s really boring, it does not concern you, but you still need to follow up with a fake laughter.

5. The “Watch this funny video” Dilemma

Similar to point number 3, your friend attempts to show you a “funny” youtube video of people failing, cats sleeping, drunk people getting wild, etc. , and the video is more than 2-3 minutes long, and deep down you really DO NOT find it funny at all, but your friend is excitedly waiting for your hearty laughter so you both can start laughing together. So at this point of time you ask yourself again whether you should play the fake laughter card, or the “I’ve already seen this video before” card, or the “This is really not funny at all” card (which no one ever plays).

This social dilemma is made 10x more awkward if the video is 10 minutes long and you sit there asking yourself what you should do.

6. The ‘Relative Problem’ Dilemma

Number 5 is a dilemma that no one really cares to admit, but it happens when a friend’s problems are relatively small compared to what you are facing now. Let’s say you are having a coffee with your friend, and they start to complain about whether they should choose to go to Australia or USA for further studies, and are extremely ‘stressed’ because they are unable to make a decision, and are afraid they might regret choosing either Country A or B. And then, you are sitting down there thinking “Jeez, I can’t even afford to study local, let alone think about comparing which country to go to.”  Your friend’s problems is clearly much smaller than yours, and you are forced to sit down there to listen to that problem, agree with it, give solutions.. while deep down, you are fighting a much bigger battle of your own. And the worst part is you can’t mention it because it will make your friend feel totally stupid for bringing their problem up

Other similar situations: Talking about their family problems while your family is really much worse off, talking about their tiny boyfriend-girlfriend scuffle while yours is on the verge of break-up, etc.

7. The Support-or-not Dilemma

This dilemma was shown in How I Met Your Mother. To sum it, it happens when your friend(s) asks you to purchase tickets for their upcoming performance or concert that you have totally zero interest in. Perhaps they are having a music orchestra performance, and your friend is sitting somewhere in the back of the orchestra with no solo at all. And then, your entire bunch of friends, including yourself, has no idea about how to appreciate music. Yea, deep down, you truly want to support all the hard work that your friend has put in, but music orchestras can really bore you to death. Hell, during the entire 2 hours duration, they will only appear for 10 minutes to showcase their single item and that’s it! You just paid $50 for that!

This also applies to: Dance concerts, Drama performances (it’s even worse when your friend is only an extra in a scene)

It’s probably not much of a dilemma if your friend is the main cast or solo performer, but this dilemma becomes bigger when your friend’s role is smaller, or only lasts a few minutes out of the 2 hour schedule.

8. The Blind Love Dilemma

Your friend is dating someone that is really bad. But your friend is also completely smitten by their significant other, that they insist they are simply perfect inside out. They are blinded by love! You are pretty sure 99.9% of the world agrees with you that they are incompatible, and you just have a gut feeling they will break up sooner or later. Deep down, you believe your friend really deserves better and you want to tell this to your friend, but you can’t, because, you know, you don’t wanna offend their feelings or suggest that they are blinded by emotion.

9. The Love Triangle Dilemma

This happens when you and your friend falls in love with the same girl, or guy. The worst possible love triangle forms, and now you need to select between chasing that person, or maintaining friendships with your competitor. Both of you initially agree to “May the best man/woman win”, and do an official handshake to ‘healthy rivalry’ and ‘no hard feelings’, but who are we kidding? You will subconsciously keep comparing your flirtatious progress with your friend, and keep wondering whether who will emerge the true winner out of this devastating triangle.

Or maybe no one wins and becomes even more awkward after both have sacrificed their friendship just to fail getting the girl

10. The Wingman/Wingwoman Dilemma

Oh man, you just asked your friend to help you score with that cute girl you just met. Your friend is so loyal to you that they perform some wingman stunt or smooth move to help you get closer to that person. And that person ends up falling for your friend instead, who was initially trying to help you out. Bummer! It’s even more awkward for your wing-friend, because they are probably feeling super guilty for ‘accidentally’ stealing your love interest.

11. The Friends-or-Lovers Dilemma

Often happens between friends of opposing genders, it happens when a random person walks up to you and your female friend, and asks whether you both are a couple or ‘Are you both together’? You frantically think of the best way to reply without making things awkward or hurting your friend’s feelings, because saying “Oh hell no!” really hurts, even if your friend has no romantic interest. And you also secretly hope that your friend also doesn’t give a similar exaggerated reaction like “Eeeew no way”, because that reply also hurts you deep down even if you don’t like your friend (in a romantic way)!

And that question also makes the both of you consider a romantic relationship even for a split second, making things really awkward right after the question is asked.

12a. The Dunning Kruger Dilemma

The Dunning Kruger effect is whereby someone overestimates their abilities, mistakenly rating their abilities much higher than what they actually are. It’s like when your friend seriously insists he can sing well, and when everyone goes for a karaoke session, he hogs the microphone and keeps singing horrendously. And everyone in the room doesn’t know how to react, and is forced to give a weak applause so that his feelings won’t end up being hurt… and no one wants to go up and tell him he really sucks.

12b. Am I Fat? Am I Ugly? Dilemma (similar to No. 12)

Am I Fat? (Yes, but deep down, I am trying to figure out whether I should tell you that bluntly, to go lose weight before putting on that outfit which makes your fats even more obvious, or whether I should put it subtly? Or whether I should just go ahead with saying “Oh nah, you look fine”. But that’s lying, and friends don’t lie… so… oh god this is a dilemma!)

This is really more awkward when your friend asks “Am I Ugly?” and (frankly speaking, the person who is asking, is below average on the universal scale. Some things you just can’t lie to people and tell them they are ‘beautiful’ instead). You wish you can tell them that they should accept themselves for who they are, and work on their personality and character instead of obsessing with their looks, but there’s just no proper reply to this, but the political answer is “You look fine”. (And you know deep down you just lied to them so they will feel happy)

13. The Best Friend Dilemma

When your close friend, but not-so-close friend, openly admits to you that you are indeed, their best friend. (But they’re really not your best friend). And you need to think of a how to reply them about the fact that you don’t see them the same way…

14. The 3-second Awkward Law

This law implies that if you put any number of people in a face-to-face group conversation, and no one says anything for 3 seconds, eyes start to shift, heads start to tilt, hands start to fidget – things become plain.. awkward. Everyone is begging (in their heads) for someone to start a question, any question, or say something. This is more commonly known as the “break in conversation” or the “Awkward pause”.

You know how that one friend will always exclaim “How come no one say anything!” after 3 seconds? That’s the friend who is socially aware of the 3-second law

15. The Dilemma of This Article

When you start to share this article with your friends, and they start to wonder whether you are guilty of having faced all these dilemmas with them before. And they also start to feel guilty for facing all these dilemmas before. And as the writer of this article, the dilemma I will face when my friends read all these dilemmas and question me whether I really felt all of these before. This is a dilemma spawned from a dilemma article.


Of course, I fully acknowledge that all these dilemmas won’t happen to best friends, or super close friends. There is always a point in friendship whereby your best buddies are brave enough to tell you the truth, and they will not lie to you about anything. If you suck at something (point 12), they will tell you that you suck. If you have truly gained weight, they will call you fat. Even if the Domino effect occurs, your best buddies will still be there for you. A loyal friend will not be involved in a silly love triangle scuffle. They will always be there to support your artistic performances.. even if they hate art. That’s why there is a clear difference between ‘friends’ and ‘best friends’, right? Now if you refer back to point number 13… Scroll up

Jackie Loh Writer The Influencer Media

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