There are so many things about your 20s that you’re somehow just expected to know.

How long are you supposed to stay at a job before leaving? If she cancels a date twice, do you try again? Who plans the second date? How quickly should you ask someone out after matching on Hinge? At what point are you supposed to meet the friends?

Nobody really sits you down and explains any of this.

And these aren’t necessarily the huge, life-changing questions we spend years thinking about. They’re the incredibly specific situations you find yourself in on a random Wednesday night when you’re staring at your phone thinking, Okay, what the fuck am I supposed to do here?

I’ve found myself asking pretty much every one of these questions at some point. So instead of pretending there’s some universal rulebook the rest of us missed, here’s how I think about them now.

If Someone Keeps Canceling Dates, Pay Attention

Getting canceled on sucks. Getting canceled on, rescheduling, and then getting canceled on again really sucks.

And while there can absolutely be legitimate reasons someone has to cancel, at a certain point you have to stop trying to figure out the hidden meaning behind someone’s behavior and pay attention to what they’re actually showing you.

A lot of early dating becomes an exercise in trying to decode someone’s interest. You wonder why they took so long to respond, whether a text meant something, whether they’re actually busy, or whether you should give them another chance.

But sometimes the answer is much simpler than we want it to be.

“A lot of the times the answers are right in front of us about how somebody feels and how interested they are in us.”

If someone cancels, makes a real effort to apologize, explains what happened, and immediately tries to make another plan, that’s one thing. If they repeatedly cancel and leave you wondering whether they actually want to see you, that uncertainty is information.

It’s the same reason I think so many of The Unwritten Rules of First Dates come down to consideration. Confirming plans, respecting someone’s time, and being clear about whether you want to see them again are small things, but they tell you a lot.

You don’t have to dramatically cut someone off after they cancel. You also don’t have to keep rearranging your life hoping the next plan sticks.

Sometimes you can just let something go.

You Don't Have to Stay at a Job Forever

The way we think about staying at jobs has changed. There was a time when spending decades at the same company could be seen as the ultimate sign of career success. Now it’s completely normal to spend a few years somewhere, gain experience, and move to another opportunity.

That doesn’t mean you should leave every job after exactly two years.

If you’re learning, getting promoted, earning more money, taking on bigger responsibilities, and still feel challenged, staying can be a great decision. But if you feel stagnant or another opportunity would clearly move you forward, you don’t need to stay somewhere solely because you’re afraid leaving will look bad.

As a general benchmark, I think around two years is incredibly easy to explain. A year and a half can be perfectly reasonable too, particularly if you have a clear reason for leaving.

The bigger thing is being able to tell the story. Why did you leave? What did you learn? Why did the next opportunity make sense?

A career doesn’t need to look perfectly linear. It needs to make sense.

That’s also one of the biggest lessons in The Best Career Advice For Starting Work. Your first few years aren’t going to be perfectly mapped out. You’re learning what you’re good at, what kind of company you like working for, what kind of boss you work well with, and what you actually want from your career.

Don't Go on Dates You Already Don't Want to Go On

There’s a difference between being nervous about a date and genuinely not wanting to go.

That distinction matters.

Maybe you’ve been on five dates recently and you’re exhausted. Maybe dating apps have started to feel like work. Maybe you’re nervous and convincing yourself you’d rather stay home. In that case, it might be worth pushing through.

But if you specifically aren’t excited about this person, the conversation hasn’t been good, you’re not interested, and you already know you don’t want to be there, forcing yourself through the date probably isn’t helping either of you.

There is one important caveat: don't cancel 30 minutes before because you suddenly don't feel like going.

You know how shitty that feels when someone does it to you. Don't do it to somebody else.

If the date is hours away and plans have been made, go into it with an open mind. If you realize the day before that you genuinely don’t want to pursue this person, it’s okay to politely end things.

Because your mindset going into a date matters.

“If you're already going into that with like preconceived notions that you don't like this person and you're not interested in this person, you don't think they're like cute or whatever it is, then it'd be better off for both of you to probably not.”

Give someone a real chance if you’re going to go. And if you know you don't want to give them that chance, don't waste their time.

Meeting the Friends Doesn't Have an Exact Timeline

If you’ve been dating someone for two months and haven’t met her friends, does that mean something is wrong?

Not necessarily.

There are too many variables to create some universal rule that says you must meet the friends after six dates or eight weeks. But if you’re starting to wonder about it, that might be a sign that you’re ready for the relationship to move into that territory.

Instead of waiting around for her to initiate it, introduce her to your friends. Say you want her to come out with everyone. Invite her to something. Make the first move.

That gives her an opportunity to become part of another area of your life, and it may naturally lead to her doing the same.

There’s actually research behind why the people around a relationship can matter. Psychology Today found that perceptions from a couple’s social network could predict aspects of the relationship’s future. Another study found that social-network support is connected with relationship development and continuation.

That doesn’t mean your friends get to decide who you date. But it does help explain why bringing someone into your world can feel like a meaningful step.

And there is something incredibly reassuring about your friends meeting the person you're dating and telling you afterward, She's great.

Apply for the Job Even If You Don't Feel Completely Qualified

Please stop waiting until you meet every qualification on a job description before applying.

You probably never will.

A job description is largely a description of the ideal candidate. That doesn't mean the person who ultimately gets hired is going to check every single box. Harvard Business Review makes a similar argument, describing job postings as more of a company’s wish list and encouraging candidates to consider roles even when they don’t meet every listed qualification.

You need enough relevant experience to make a case for yourself. From there, your ability to learn, communicate, adapt, and demonstrate why your experience translates to the position matters enormously.

“Nobody comes into this knowing exactly what to do.”

Every new job requires learning. You have to understand a new company, a new boss, new coworkers, new systems, and completely new ways of doing things. You aren't supposed to walk through the door on your first day knowing everything.

If a job feels like a step up but you can make a legitimate argument for why you're capable of doing it, apply.

Let them tell you no.

Don't do it for them.

You Should Probably Plan the Second Date

If the first date went well and you're sitting around wondering who is supposed to reach out about the second one, my answer is pretty simple.

You should.

Tell her you had a great time. Tell her you'd like to see her again. Then actually suggest something.

Don't send, “We should do this again sometime.”

Say, “I had a great time. I'd love to take you out again. Are you free Thursday?”

Then have an idea of where you want to go.

I also think it's completely fine for the guy to take the lead on planning the first few dates. It shows intentionality. It makes the other person feel wanted. And there is something romantic about someone saying, I want to take you here.

Eventually, you’ll naturally start making plans together. Early on, though, don't sit around waiting for her to plan date two because you think it's technically her turn.

If you want to see her again, make it happen.

Casual or Serious Usually Starts to Reveal Itself

One of the hardest things about early dating is figuring out what the other person actually wants.

Are we just hooking up? Are we dating? Could this become a relationship? Do they even know what they want?

I don't think you necessarily need to sit someone down on the first or second date and demand a definition. Give it a little time.

Pay attention to how often you're talking, how much effort you're both making, whether you're planning future dates, what you're saying to each other, and whether the relationship feels like it's progressing.

That pattern is something I talk about a lot in The Early Dating Questions Literally Every Guy Has. One individual text, date, or interaction rarely tells you everything. Consistent effort usually tells you a lot more.

You can also put something out there yourself.

Tell her, “I'm really liking where this is going.”

Then listen to how she responds.

You don't always have to ask someone a huge, intimidating question to understand how they're feeling. Sometimes you can give them an opening to tell you.

After a few dates, if you still don't know and knowing matters to you, then ask. Wanting clarity isn't a bad thing.

You Don't Need to Talk on Hinge for Three Weeks

There's another dating-app question that somehow nobody teaches you: how long are you supposed to talk before asking someone out?

I learned this one by doing it wrong.

When I first got on Hinge, I would basically match with someone, exchange a few messages, and ask them out. And sometimes it worked.

The problem was that we'd get to the date knowing absolutely nothing about each other.

You don't need to become pen pals, but you should probably have enough of a conversation to know that you're actually interested in meeting this person.

Talk for a little while. See if there's any flow to the conversation. Learn something about them. If you want to, move from Hinge to texting.

Then ask them out.

You don't need to wait three days because somebody on TikTok told you it makes you look mysterious. You also don't need to ask within your first three messages because you're terrified the match is going to disappear.

Have enough of a conversation to know you want to meet them.

Then meet them.

Your 20s Are Probably When You Should Start Dressing Better

At some point, the clothes you wore throughout college stop feeling like the clothes you want to wear everywhere.

Usually it happens because something in your life changes.

You start your first real job. You start going on more dates. You have weddings. You go to nicer restaurants. You look around your closet before going somewhere and realize you genuinely have no idea what to wear.

That's probably your sign.

You don't need to throw away everything you own and suddenly spend thousands of dollars on clothes. Start building a wardrobe that actually fits your life.

Buy a few things that fit really well. Figure out what you like wearing. Invest in pieces you can wear repeatedly instead of buying something cheap every time an event comes up.

Because clothes aren't only about how other people see you. They're also about how you feel when you walk out the door.

When you feel like you look good, you carry yourself differently.

And Here’s The Thing

I don't think anybody reaches a point where they suddenly know how all of this works.

I'm 26, and I still find myself asking these questions.

Your 20s are filled with these tiny moments where you're trying to figure out what you're “supposed” to do. When do I text her? Should I go on this date? Is it weird that I haven't met her friends? Am I leaving this job too soon?

Most of the time, there isn't one universal rule.

But there usually is a next move.

Pay attention to the effort someone is giving you. Be respectful of other people's time. Apply for the opportunity that scares you a little. Initiate the second date if you want one. Introduce her to your friends if you're ready for that. Ask for clarity when you need it.

You don't need to have everything figured out.

You just need enough information to figure out what to do next.

Frequently Asked Questions

What should you do if someone cancels a date twice?

Pay attention to what happens after the cancellation. If they apologize, explain what happened, and actively try to make another plan, there may still be interest. If they repeatedly cancel without making an effort to see you, stop chasing the date and move on.

How long should you stay at a job before leaving?

There is no exact rule, but around two years is generally an easy amount of time to explain to a future employer. Leaving earlier can also make sense if you have a better opportunity, aren't growing, or have a clear reason for making the change.

Who should plan the second date?

If you want to see her again, don't wait around trying to figure out whose turn it is. Reach out, tell her you had a good time, and suggest an actual plan for the second date.

How do you know if someone wants something casual or serious?

Look at the pattern of effort over the first few dates. How often are you talking and seeing each other? Are you both making plans? Does it feel like things are progressing? If you're still unsure after a few dates and the answer matters to you, ask.

How soon after matching on Hinge should you ask someone out?

You don't need to spend weeks messaging, but you also don't need to ask immediately. Have enough of a conversation to establish that you're interested in each other and have something to talk about, then suggest meeting in person.