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20 uncomfortable conversations you can’t avoid in your 20s Everybody has their list of questions to run down when talking to you as a 20-something. Be prepared for these.

The life of a 20-something is all about contemplating the rest of their life. How absolutely burdensome is that? “Please plan the next 70 or so years of your life right now. Shouldn’t be too difficult. Well? We’re waiting!”

Everybody wants to know exactly what your plans are for right now, five years from now, 10 years from now, and so on and so forth. “It’s about time you figured this whole thing called life out even though you’ve barely had a chance to experience this whole thing called life. No rush, but you really should get on it right now.”

With so many questions for you to answer, either while looking in the mirror and weeping, from your parents or fellow 20-somethings feeling the terror of life coming down upon them, there’s inevitably going to be plenty of things you don’t want to talk about, but simply have to.

You going to live here your whole life?

Everybody wants to know if you ever plan on leaving your home town to see the world. They want to talk to you about either they “plan on doing that,” or how they “wish they had done that.” Parents encourage you to leave, then guilt you when you do.

Are you dating?

If your answer has anything to do with focusing on your future, the contradictory ploys will come into play about how you won’t be able to find someone when you’re older.

What are you studying?

Be prepared to justify why this is the correct educational path for you to everybody you meet over the next handful of years. When they don’t seem to understand or care at all, try your hardest not to feel like a complete buffoon for choosing what you’ve chosen.

What are you going to do with that?

Now’s the time you’ve got to justify that there are some decent career options associated with what you’ve chosen to study. Nevermind how completely condescending the nature of this question sounds — you have to be upbeat and excited in your response.

Thought about getting your master’s?

“Hey, hope the last four or more years of your life wasn’t too much of a drag. Have you considered going further into debt for something that will simply keep your from getting the experience you need to get the experience you need to get the job you want?”

How’s the job hunt coming along?

Oh boy, you cannot avoid the most humbling question of them all, when the answer is usually in fact, “It’s coming along rather dismally.” Be ready for their less than inspiring response: “It’ll happen when it happens.”

Uh, no shit!

So, what do you do?

Maybe now you’ve finally made it out of your hometown and the job hunt finally paid off, but now you’ve got to justify the last however many years of your life to a new set of people you hope will like you enough, so you’re not completely alone in a new city. That’s a lot of pressure, especially when you explain your line of work and they say, “Huh…” and nod their head with a half smile.

How’s work?

“Well, I’m at the bottom of the totem pole and nobody seems to notice what I do, but you know, just paying the bills that are insurmountable from all that college I’m not sure I needed.” You obviously can’t respond with that, but it’s the reality of the situation.

Is that really what you want to do with the rest of your life?

Yeah, thanks for making us question all the hard work we’ve put in to make it to this meager moment in our lives. Guess it’s time to reconsider everything and start over? Wait, there’s no time for that — the future needs to be planned out now!

What are your salary requirements?

Thanks for this one, workforce. It’s rather embarrassing to reply, “Please, I’ll take anything!”

Do you have a primary doctor/insurance at all?

“HAHAHAHAHAHAHAHAHA! Oh, wait…that was a serious question? Yeah, no.”

When is the wedding?!

In your 20s, it only takes a few months of dating someone for everyone to start chiming in about hearing wedding bells. Try to avoid audibly gulping and adjusting the neckline of your shirt when you honestly want to say, “We’re waiting, for now.”

Thinking about having kids?

Well, if the possibility of a wedding is out there, you may as well start considering reproducing, right? Those salary requirements you requested (begged for) can support a little one too, right? No? Oh.

Seriously, when is the wedding?

“You can’t avoid us forever, so just answer us: WHEN IS THE WEDDING?!”

This comes up routinely and only increases in pushiness as you grow older in your 20s with the same person you’ve been dating.

Still enjoying work?

It’s best to just say, “Yes,” because if you’re honest with them, you may actually have to embrace that mirror weeping moment with yourself and try to figure out if completely changing your life path is doable. That’s too scary to think about when you’re having a hard enough time not pulling money from your savings as it is.

Would you like to donate to the alumni association?

No, but please do sell me on this until I have to embarrassingly say I can’t afford to do so.

Whoa, I haven’t seen you since high school! What have you been up to?

Great, as if seeing these people’s updates on social media wasn’t enough to make you question your life, now you’ve got to face them face to face.

“Oh, you know, just working and trying to not cry on a daily basis. You? Oh, you got your Master’s? You’re a doctor? Good for you.”

Those babies aren’t going to make themselves, right?

Again, the repetitive nature of this question keeps creeping in. Those who bring this up really are just reinforcing your pending marriage with a tactile question of a future family. Don’t be fooled by the subliminal message.

You should just be having fun at this age…

Oh, and then the old people decide to mock you for all the things you’ve been trying so hard to achieve and plan out for the next 70 years or so by telling you to soak up being young.

“Thanks for worrying me to death about whatever the hell a 401(k) is, then reminding me that I should be drinking every night if I so choose.”

I remember when I was young…

Great, now you’ve got listen to a parental figure reminisce about their 20s as if life is a fleeting passage of depression in the decades following. Really makes all this planning seem unnecessary and cruel.

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1 thought on “<span class="entry-title-primary">20 uncomfortable conversations you can’t avoid in your 20s</span> <span class="entry-subtitle">Everybody has their list of questions to run down when talking to you as a 20-something. Be prepared for these.</span>”

  1. “No, but please do sell me on this until I have to embarrassingly say I can’t afford to do so.”
    There’s also the “can you hold on for a little bit” and then you just go about your day


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