The Do’s And Don’ts Of Dating In Your 20s

Dating sometimes most of the time sucks.

In the age of Facebook-stalking and a new dating app popping up every week, the rules are constantly changing. Navigating the dating world as a 20-something has never been more difficult.

Sure, long-distance relationships in our grandparents’ time meant having to wait weeks to receive a letter from their significant other, but they never had to deal with the stress of the gray texting bubbles.

We’d gladly choose a carrier pigeon over those guys any day.

Luckily for us, TV has finally caught up to the woes of modern-day dating. We no longer have to feel alone as we jump from one romantic mishap to the next. We can now watch our favorite characters go through their fair share of cringe-worthy dating situations and actually relate.

When Hulu asked us to write about the “do”s and “don’t”s of modern dating using scenarios from their new original series, Casual, we were totally on board. Plus, it gave us an excuse to watch TV at 2 pm on a Tuesday because “It’s for work”.

What we found was that the characters, albeit in different walks of life, were facing scenarios that most of us have or will go through in our romantic endeavors. So what better source to draw inspiration from than that?

Take it all with a grain of salt, or a heavy sprinkling. We’re not claiming to be experts in this area, but hey, we can try.

Social Media Stalking Research

Scenario from Casual Episode 1:

“You ever online date?”


“Um, do you do any prep or do you just go in blind?”

“I do my research, I don’t have a death wish.”

“So you mean on Facebook?”

“Yes on Facebook, and Instagram, Twitter, LinkedIn, Vine, Lulu, Match, OkCupid…”

We’ve all been there – 82 weeks deep into the Instagram account of our latest love interest. The black hole of social media sucks you in and suddenly you know more about a stranger’s life (where they went on their last 5 vacations, how they take their coffee in the morning, etc.) than your own cousin’s.


Check out their social media accounts to get a sense of who they are and actually follow them [gasp]. Giving them a follow doesn’t mean anything more than that you want to get to know them (which you do because you like them, remember?) So don’t overthink it or treat it like a wedding proposal. It’s just Instagram.


Make a fake account to secretly stalk them so you won’t actually have to “follow” them. Yes, you think you’re super stealthy, but come on. Also, try to keep the research within the last year. It’s not fair to pass judgments on where people were over a year ago. A lot can happen in 52 weeks. Just think, 52 weeks ago Zayne was still with 1D sigh.

Differences vs. Deal Breakers  

A great exercise in dating is to come up with 5 non-negotiables for the person you intend to seriously date. Basically 5 things that are so important to you, you won’t sacrifice those standards no matter how dreamy their man bun might be.

Maybe they have to be a dog person, from the same religious background as you, or you know you just. can’t. date anyone who seriously likes Nickleback. Having 5 solid “deal breakers” will keep you from digging deeper into a relationship that will just ultimately end in a breakup.

But don’t get too picky.

Many of us date with a “more fish in the sea” mentality, so we’re often quick to release someone the second they rub us the wrong way. And that’s just not fair.

We’ve all had bad days. We’ve all slipped up on a first date. We have differences, and that’s what makes other people cool and interesting to be around because they’re not like us.

In Episode 1, Alex quickly dismisses his Paleo, CrossFit-crazed date before dessert even comes. Maybe the ability to eat processed flour is one of his non-negotiables, in that case, good for you Alex. But chances are it was just another case of being just a little too picky.


Have standards and don’t you dare compromise on those.


Be so picky that you pass up a potentially awesome person.

Drinking On The First Date 

First date – hell, fourth date – jitters are inevitable. And for some of us, getting through a first date without a drop of liquid courage is almost unheard of. But where’s the line and how do we make sure to not cross it?


Have a cocktail while getting ready to relax and calm your nerves. No shame girl. During, don’t feel like you have to go drink-for-drink with your date. Not all livers are created equal. You know your tolerance level.

On the flipside, no shame in keeping an emergency flask in your purse. If things start to go south or the nerves creep up, sneak off to “powder your nose”. It will be such a cute anecdote to tell at your wedding rehearsal dinner.

But most importantly, make sure a friend or roommate knows where you are and have a plan to get home besides your date. Hello, Uber.


Be stupid. A little alcohol can help you bring out your dazzling personality. A lot of alcohol can bring out a lot of bad decisions…which leads to the next point.

Hooking Up On The First Date

We all have our rules. No kiss till the second date, no strings attached, let them make the first move, etc. And from time-to-time we all break them.

Like we’ve said, it’s good to have standards, but don’t focus so much on the “rules” as much as how you’re feeling. There’s something to be said about intuition and guts – so listen to yours.


Whatever the hell you want as long as it makes you feel happy and whole, and most importantly safe.

But if you’re feeling confused, a good rule of thumb is to look back and see how you felt about situations in your past. If things are starting to really heat up but you remember your last one-night stand left you feeling awkward and empty, slow things down.

Or if you know your last relationship failed because you never said what you wanted, make the first move girl!


Feel pressured to do anything you don’t want to do, or even have to give a reason why. If something doesn’t feel right, it just doesn’t and you don’t have to justify that.

Also don’t fall victim to the myth of the prude/slut paradox. You know, the polarizing societal standard that says women are either one or the other. It’s a load of crap. And don’t waste your time on anyone who subscribes to that false way of thinking. Ain’t nobody got time for close-minded people.

Feedback from Your BFFs

Friends can be the ultimate sounding boards when it comes to dating– especially friends in the same life stage as you.

But getting advice from people in different walks of life is beyond important. Sometimes the most unlikely of people will have incredible wisdom.

Although it might not be obvious how a middle-aged divorcee, eternal bachelor and headstrong high schooler can benefit from each other in the love-advice department, the main characters of Casual are prime examples of the positivity that can come from letting an “outsider” weigh in on your dating woes.


Gab, vent and stay up late drinking wine and dishing about your #singlegirlproblems with your besties. But also talk to your mom, your older sis, a trusted co-worker, your Seamless delivery guy.

Outside opinions can help put your situation into perspective in a way people in your same situation just can’t.


Feel like you have to listen to every piece of advice, though. Everyone will have their ideas and opinions, and not everyone will be right.

Also, don’t feel like you need your friends’ opinions on every situation you find yourself in. It can be super liberating to make your own decisions with zero outside help.

The big takeaway

You do you.

Just like snowflakes, no two dating pasts or presents are exactly the same. The best thing you can do for yourself is to take the pressure off. There’s no perfect age to find “the one” or settle down. And it’s okay to make mistakes. Just learn from them and don’t beat yourself up.

At the end of the day, no one else should hold the key to your happiness but yourself. So focus on making yourself happy first. If others come along and decide they want to bask in your incredible presence, well then lucky them.

Featured image by Amelia Kramer

dating in your 20s

This post is brought to you by Hulu’s Original series Casual. Join the conversation; check out the latest episode of Casual on! New Episodes Wednesdays.

Molly Longest

Co-founder, Creative Director Her heart belongs to: leather jackets, live music, Moscow Mules and getting that perfect picture Her guilty pleasures: frequenting the taco truck down the street a minimum of two times a week and talking to strangers' dogs in Central Park

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