Asking Her Out, Moving On, and Starting New: Real Advice for Guys in Their 20s

There are so many things about being in your 20s that you feel like you should already know how to do.

You should know when to ask someone out. You should know whether a relationship is going anywhere. You should know how to handle a new job, how to communicate with your girlfriend, and how to stop worrying about everything that comes next.

But who actually teaches you any of this?

I think one of the hardest parts of being in your 20s is constantly finding yourself in situations you've never experienced before while feeling like you're supposed to know exactly what you're doing.

And because everybody else seems to have it figured out, you start wondering whether you're the only person struggling with these things.

You're not.

Whether you're trying to figure out when to ask a girl out, deciding if you should keep seeing someone, or wondering if you're doing a good job at work, there's usually a much simpler way to approach these situations than you think.

Here are six questions I think almost every guy in his 20s has asked himself at some point, and how I'd approach each one.

How Long Should You Talk to a Girl on a Dating App Before Asking Her Out?

I think almost every guy who's used a dating app has experienced this.

You match with someone, send a message, get a response, and start having a conversation. Things seem to be going well, but now you're wondering how long you're supposed to keep talking before asking her out.

Ask too quickly, and you might not know anything about her. Wait too long, and you risk turning what could've been a date into an endless conversation that never goes anywhere.

I've made both mistakes.

I've asked someone out almost immediately, only to realize on the date that we knew absolutely nothing about each other. I've also waited too long and watched the conversation lose momentum.

My advice is to build a little bit of common ground, then make a move.

You don't need to know her entire life story. You just need enough of a conversation to feel like you have something to talk about when you meet.

Maybe you've talked about her dog, a trip she took, or something you both find funny. Having even one or two things in common makes that first date feel a lot less intimidating.

I generally think five to ten messages back and forth can be enough to get a sense of someone. From there, you can exchange numbers and, once you've established some chemistry, suggest getting together.

There's no universal timer, but you don't need to spend days messaging someone before asking her out.

The goal isn't to build an entire relationship over your phone. It's to figure out whether you'd enjoy spending time together in person.

And if you're struggling with dating apps in general, I've also written about The Dating and Career Questions Guys Have Right Now, including how to handle common dating situations without overthinking every decision.

Should You Keep Dating Someone When Something Feels Missing?

This is one of the harder questions to answer because there's no exact formula.

Maybe you've been on a few dates with someone who's genuinely great. She's kind, attractive, fun to talk to, and seemingly everything you're looking for.

But something doesn't feel quite right.

You can't necessarily explain what's missing. You just know you haven't felt that connection you're hoping for.

My advice depends on how long you've been seeing her.

If you've only been on two or three dates, I think it's worth giving things another chance. Sometimes a connection takes time to develop, especially when you're still getting comfortable around someone.

One more date might help you see something you hadn't noticed before.

But there's an important distinction between giving someone a chance and forcing yourself to feel something.

You can't go into the next date treating it like a test where she has two hours to convince you that she's the right person. That's not fair to her, and it's not going to help you enjoy yourself.

Instead, be present during the date. Then, afterward, ask yourself a few questions.

Are you excited to see her again? Do you find yourself wanting to talk to her? Would you be disappointed if you never saw her again?

I think those questions tell you a lot more than constantly trying to determine whether you've felt some magical spark.

If you've already been on seven or eight dates and you're still wondering whether you're interested, that's a different situation. At that point, you probably need to be more honest with yourself about what you're feeling.

You don't need to feel everything immediately, but you shouldn't have to convince yourself that you like someone either.

How Do You Get Better at Being Where You Are Right Now?

I love this question because it sounds simple, but it's actually asking something pretty important.

How do you stop constantly thinking about what's next and start enjoying what's happening right now?

My first piece of advice is probably the most obvious: put your phone away.

It's incredibly difficult to be present in a conversation when you're simultaneously checking messages, scrolling Instagram, or thinking about whatever is happening on your screen.

But I actually think my second piece of advice is even more useful.

Ask more questions.

When you ask someone a question, you have to pay attention to their answer. And if you want to ask a follow-up question, you have to listen to what they're saying.

It's a simple way to make yourself more engaged in whatever situation you're in.

Whether you're on a date, spending time with your friends, talking to your family, or sitting in a meeting at work, being curious about the people around you naturally brings you into the moment.

You stop thinking so much about what you're going to say next because you're actually interested in what the other person is saying.

You don't necessarily need some complicated mindfulness routine. Sometimes you just need to put your phone in your pocket, look at the person in front of you, and ask another question.

And this goes beyond conversations. A lot of us spend so much time thinking about our future that we forget to appreciate what's happening in our lives right now.

I explored this further in How To Stop Worrying About the Future and Live in the Present, because I think being present is one of the most useful skills you can develop in your 20s.

When Should You Introduce the Girl You're Seeing to Your Friends?

My answer to this one might surprise you.

I think the earlier the better.

I'm not saying you need to introduce someone to your entire friend group on the second date. But if you've been seeing someone for a little while and things are going well, I don't think you need to wait months before bringing her around.

Your friends are an important part of your life. And if this relationship becomes serious, the person you're dating will become an important part of that life too.

The sooner those two worlds can comfortably come together, the better.

Maybe you're going out with your friends after a date and invite her to join. Maybe there's a casual group dinner or a weekend hangout where she could come along.

It doesn't need to be some big, formal introduction.

I also think there's something really reassuring about hearing your friends tell you they like the person you're seeing.

There's nothing better than getting a text from a friend afterward saying they think she's great.

Of course, your friends don't get to decide who you date. But when the people you care about get along with the person you're seeing, it makes everything feel a little more comfortable.

And if you're actively avoiding introducing someone to your friends, I think it's worth asking yourself why.

Ultimately, it's about building a relationship where both people feel comfortable becoming part of each other's lives.

Should You Tell Your Girlfriend When Something Small Bothers You?

Not every annoying thing needs to become a conversation.

I think that's an important part of being in a relationship that people sometimes overlook.

When you're spending a lot of time with another person, they're inevitably going to do things that bother you. And I can almost guarantee you're doing things that bother them too.

That's normal.

If something happens once or twice and isn't particularly important, sometimes the best thing you can do is let it go.

But if it's something that happens constantly, genuinely bothers you, and starts affecting how you feel around your partner, I think it's worth bringing up.

Because if you've been bothered by something for months, ignoring it probably isn't going to make those feelings disappear.

The important part is how you communicate it.

You don't want to turn a small annoyance into an unnecessary argument by making the other person feel criticized or attacked.

Approach it gently, explain what you're feeling, and remember that the goal is to improve the relationship, not win an argument.

The American Psychological Association's Guide to Healthy Relationships reinforces how important open communication is, particularly when addressing concerns before they turn into resentment.

And that doesn't mean every conversation needs to be serious.

Sometimes it's as simple as saying, "Hey, would you mind not doing that? It's just one of those little things that bothers me."

A healthy relationship isn't one where nothing ever bothers you. It's one where you know which things are worth discussing and how to discuss them respectfully.

How Do You Know If You're Doing a Good Job at Your First Real Job?

I think the best way to explain starting a new job is with an analogy.

Starting a new job is like jumping into the passenger seat of a car that's already moving at 75 miles per hour.

Everyone around you knows where they're going. They know how the car works, who's driving, what route they're taking, and why they're headed in that direction.

And then you get in.

You have no idea what's happening.

You're trying to figure out where you are, what you're supposed to be doing, and how everyone else seems to know so much more than you.

But here's the thing: you just got in the car.

You're not supposed to know everything yet.

I think this is especially important to remember when you're starting your first real job. You're walking into a business that was operating long before you arrived, surrounded by people who have had months or years to understand how everything works.

You're comparing your first few days to someone else's hundredth or thousandth day.

That's not a fair comparison.

So instead of expecting yourself to know everything immediately, spend your first few weeks learning.

Understand what the company does, how it makes money, what your team is responsible for, and what your manager expects from you.

Ask questions. Pay attention. Have conversations with the people around you. Check in with your boss to make sure you're focusing on the right things.

Those are all signs that you're doing a good job, even if you don't feel particularly confident yet.

According to Indeed's Guide to Succeeding in a New Job, the first few weeks should focus on understanding your workplace, building relationships, and clarifying expectations with your manager.

And I think it's worth remembering that this feeling doesn't necessarily disappear when you get older or have more experience.

I've started multiple jobs, and I still experience it.

Every company operates differently. Every team has different expectations, and every role comes with a learning curve.

I also wrote about this feeling in The Things Nobody Tells You About Starting a New Job, because I think so many people mistake being new at something for being bad at it.

Those are two completely different things.

You need to put your seatbelt on before you can start figuring out how to drive.

The Bigger Lesson: You're Not Supposed to Have Everything Figured Out

The interesting thing about all of these situations is how different they are, but how much they have in common.

One guy is wondering whether he's waiting too long to ask someone out. Another is worried that he doesn't feel enough of a connection with someone he's dating. Someone else is starting a job and feels like he's already falling behind.

They're completely different situations, but underneath them is a similar feeling.

Am I doing this right?

And I think that's one of the most universal experiences of being in your 20s.

You're constantly doing things for the first time while feeling like everyone around you already knows what they're doing.

But most people are figuring things out as they go.

You don't need to know exactly when to ask someone out. You don't need to immediately know whether someone is right for you. And you definitely don't need to know everything during your first week at a new job.

You need to be willing to try things, make decisions, learn from your experiences, and adjust along the way.

That's how you get better at all of this.

And as the American Psychological Association's Conversation on Building Strong Relationships highlights, relationships are built through attention, communication, and learning how to respond to one another.

Those are skills you develop through experience, not things you're automatically supposed to know.

And Here's The Thing

I think a lot of guys spend their 20s feeling like they're behind in situations where there's no actual timeline.

You think you should know how to date because you've been dating for years. You think you should know how to handle a relationship because you're an adult. You think you should understand your job because someone hired you to do it.

But experience doesn't automatically mean you have every answer.

Sometimes you're going to ask someone out too early. Sometimes you're going to give a relationship one more chance and realize it isn't right. Sometimes you're going to sit at your desk and have absolutely no idea what's going on.

And that's part of figuring things out.

What matters is what you do next.

Ask the question. Have the conversation. Go on the date. Learn something new. Give yourself room to figure things out.

Because chances are, whatever you're wondering about, there's another guy out there wondering the exact same thing.

And the sooner you realize that, the less alone you'll feel trying to figure it all out.

Frequently Asked Questions

How long should you talk on Hinge before asking someone out?

Long enough to establish chemistry and find some common ground. A few meaningful exchanges can be enough to suggest a date.

How many dates should you give someone if there's no spark?

If you've only been on two or three dates and see potential, give it another chance. If you're still unsure after several more dates, it may be time to move on.

When should you introduce a girl to your friends?

Once you're comfortable with each other and things are progressing. Around the third or fourth date can be a natural opportunity.

Should you tell your girlfriend everything that bothers you?

Not necessarily. Let small, occasional annoyances go, but communicate recurring issues kindly before resentment builds.

How do you know you're doing well at a new job?

Focus on learning, asking questions, understanding expectations, and getting feedback. You aren't supposed to know everything immediately.