5th date: 15 things you absolutely should know by the 5th date

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If you’re already planning a fifth date, congrats!

There’s no doubt about it—you’re both into each other. You probably have good chemistry otherwise you wouldn’t reach date number five.

But if you’re considering the possibility of starting a relationship with them, chemistry just isn’t enough.

To know if you’re truly a good match, here are some of the things you must absolutely know about the person you’re dating by the fifth date:

1) Whether they’re looking for something serious or casual

During your first four dates, you got a feel of each other. You discovered their taste in music, how they smell, their favorite flavor of ice cream. You probably even held their hand.

But you didn’t want to go too deep at that point because you’re afraid they might think you’re moving too fast. The fifth date, however, is the right time to get a little more clear of your intentions.

You have to know if they want to be in a relationship or if they just want to date around.

It would be hard if only one of you wants to get serious. The one who’s ready to have a relationship will feel they’re being strung along, while the one who wants something casual would feel suffocated and guilty.

You have to want the same thing. Otherwise, one of you will just end up hurt even without them meaning it.

2) What their typical day looks like

If you’ve been dating for a while now, you should somehow have an idea of their daily routine and what they do on the weekends.

However, it would help to ask them this directly so you get a clearer picture.

Knowing about their day would give you a lot of important information aside from their daily schedule!

For example, you’d know whether they’re a morning person or a night owl, how much time they spend at work, their hobbies, who they usually hang out with, and many other things that could give you an idea of what it’s like to live with them.

How is this useful?

Well, let’s say you’re already in a phase in your life where you don’t like partying on the weekends yet partying is what they live for, so you might want to think how this will affect you if you both decide to start a relationship.

By the fifth date, you should know if you like the way they live their life on a daily basis because how they live their life will affect you greatly.

3) What kind of future they want

Given that many people adhere to a ‘five date rule’, where they wait until the fifth date to decide whether they’ll go ahead and make it official or break it off, it’s no surprise that it’s at this stage that a deeper connection is most important.

One of the best ways to do that is by talking about dreams and aspirations.

Whether you’re ready to settle down or you’re just taking things slow, it’s important to know how the person you’re dating sees their future.

Do they dream of becoming a CEO of a tech company or a rockstar who tours all over the world?

Do they want to stay in the city or become a nomad with no permanent address?

If they want to become a nomad yet you prefer to stay put in your city because you want to establish connections for your business, then you’ll be building a relationship that you know will crumble one day.

It doesn’t have to be too detailed, of course. You’re not getting married yet! Besides, it’s difficult for anyone to really be clear about the future, even you.

But it would be nice to get a general idea of the kind of life that they’re aiming for to know if you’re going to be good together, and that means neither of you will make a major sacrifice just to be together.

4) The things they’re passionate about

If you’re the kind of person who can’t be with someone who has no strong interests, hobbies, and opinions, then figure that out right away.

I’m sure they’ve mentioned some hobbies on the first few dates but you have to know what they’re really, really into…something they’re willing to spend time and money on, something that really excites them.

You’ll probably figure this out by observing rather than just asking them. Look back on your conversations and recall what they said they’re passionate about, then observe if they’re consistent.

Did they mention it again? Are they actually doing those things?

If they kept talking about how they want to end world hunger on your first date and they talked to you about it again on your third date and even donated some money to the World Food Programme, then they must not be faking it.

But more than knowing if they actually have things they’re passionate about (because most of us do anyway), you have to ask yourself if their interests match yours or they’re something you can truly live with.

If they’re into gaming, then expect they’ll game a lot. Can you live with that?

5) Their dealbreakers

By the fifth date, you should already know what they can’t stand in a partner.

Do they absolutely hate it when their partner is clingy? Maybe they broke up with someone because they’re being too needy in the relationship. If you’re aware that you’re a clingy person, you should tell them.

If they say they can’t be with someone who snores, tell them if you do.

If they say they can’t be with someone who drinks, tell them if you do.

That way, they’ll be fully aware of what they’re about to deal with if you decide to become a couple. This will also take the burden off your shoulders because they’re fully aware of what they’ll be getting.

As for you, knowing their deal breakers will also make you aware of the possible challenges you will have, what you should try to improve in yourself, and whether a relationship with them would be worth it.

6) Their relationship history

By now, you should really know how many people they’ve dated and whether they’ve been in a long term relationship or not.

The truth is, it really doesn’t matter if they had zero or twenty relationships but what’s important is how they are when they had these relationships.

Let them reflect on how they are as a partner and why they think their relationships failed. The best way to do this is by telling them how you think about your own dating history.

Do they have incredibly high standards that’s why they’re single? Do they feel that they have a problem committing to someone after the New Relationship Energy has faded?

Knowing about these details can lead to clues of the kind of person they are, and how they love—two very important things to know beforehand instead of just discovering them for yourself later on.

7) If they have any kind of addiction

Trust me, you don’t want to wait until you’re officially together to ask them if they have some kind of addiction whether it be alcohol, porn, or drugs. If only it isn’t rude to ask about it on the first date, you should.

But asking more personal questions on the fifth date is totally acceptable—even expected— as long as you know how to communicate well.

You have to be non-judgmental and compassionate. If they say that they used to be an alcoholic but stopped a year ago or yesterday, don’t judge them. They even deserve praise because they’re able to let go of something that’s bad for them.

This is a very important fact that you should know early on. It can stop you from entering the relationship if it’s truly dealbreaker for you. That way, you won’t be wasting each other’s time.

And if you ever decide to have a relationship with someone who has or had an addiction, it could help you prepare for the future. For example, if they’re an ex-alcoholic, you probably should not pressure them to go bar hopping with you.

8) Their “baggage”

If they have anything big that could affect how you’ll both live your life if you do get together, then you should know them by now.

If they have children, you should already know before the fifth date.

If they have a lawsuit or big debt, then they should have mentioned it to you already.

These are important things that should be divulged while you’re still dating and not while you’re already a year in the relationship. It’s only fair that you know what you’re about to enter.

Of course, it goes without saying that you have the obligation to reveal your baggage too.

9) How close they are to their family

Being with someone who’s close to their family means that how their family sees you could potentially affect your relationship. To some people, you’ll not only be getting in a relationship with them, but with their whole family.

It could also mean that there’s a possibility that problems related to codependency, attention-seeking in-laws, or a toxic family dynamic could arise in the future.

Ideally, we want to be with someone who loves their family but knows how to set their boundaries. It’s good to know this early on so you can ask yourself if this actually works for you.

10) Their views on marriage and kids

If you’ve already done some self-reflection and you’re 100% sure you don’t want marriage and kids in the future, then don’t start a relationship with someone who absolutely wants those things!

Not only will that be unfair for them, it might even pressure you to do them just because you’re in love with them. Don’t do this to them or to yourself. You’ll later regret it.

In fact, these things should be discussed on the first or second date if you’re dating to marry.

There are so many cases of couples breaking up for this reason. They thought they could convince the other to change their mind, but that rarely happens.

If they’re already adults, especially if they’re over thirty, believe them and don’t take their word lightly when they say they don’t want those things.

You don’t want to be one of those people who’ll cry and say “but I thought they’ll change their mind.”

11) If they’re kind

Genuine kindness, generosity, and honesty are quite difficult to spot because you both need to be in a situation that requires those traits to be shown. And who knows if they could just be faking it when they do it while you’re there, right?

But what can easily be spotted is bad behavior.

By the fifth date, hopefully you can detect if they have detestable qualities that you wouldn’t want in a partner.

Pay attention if they’re kind to people who can’t do anything for them.

Pay attention to how they treat pets.

Pay attention to how they view those who are suffering—the homeless, people with special needs, the misunderstood.

Pay attention to how they view women and those from another race.

Of course you probably have an idea of who they are but try to go back to your conversations and look out for signs that made you go “woah, not so nice.” By date number five, you’ve probably collected a lot of them if they’re assh*les.

12) Their level of clinginess

Most of us put our best foot forward on the first few dates. Behaviors such as clinginess will only be obvious when you’re already in a relationship.

However, if you’ve been dating around for a while now, you can pretty much tell if a person is clingy or not.

If they send very few messages during the day, they might not be clingy.

If they reply fast and are not afraid of sending multiple messages, they might be a little clingy.

Quite simple.

Now take note that clinginess doesn’t mean someone is needy or has a tendency of having toxic traits. It’s just that their desire to express affection is high.

If you’re both clingy, then you’re probably a good match.

If you’re both not so clingy, then maybe that’s just alright, too.

It’s only problematic if one of you is too clingy that it makes the other person feel suffocated. That might not end up well for you if you’re still on the fifth date yet you can sense you’re truly incompatible when it comes to your clinginess level.

13) What they think about the things that are important to you

By the fifth date, you should know what they think about the things that are important to you—things such as your beliefs, morals, and any causes that you may support to name a few.

While it would be understandable that you might want to avoid talking about these heavier topics on your first two dates, by your third or fourth you should be comfortable enough to discuss them so that you can test your compatibility.

After all, if you’re going to commit to a relationship, you might as well make sure that you agree or, at least, not conflict when it comes to the things you hold close to your heart.

Think about it. Let’s say that you’re a meat lover, and they turn out to be a vegan who hates meat lovers with a passion. What would mealtime look like? Now, imagine if they work for PETA.

You really won’t work out, not unless one of you compromises on their beliefs!

14) If they’re active or passive

No, I’m not talking about whether they are workaholics or bums (although those things, as mentioned above, are very important too!) , we’re talking about whether they have a tendency to be more passive or active if you’ll have a relationship.

Are you the one always initiating the dates?

Are you the one who’s always planning, organizing, figuring things out so everything will go well?

You can tell on your fifth date, for sure!

Some people prefer to take the backseat when it comes to maintaining a relationship and this imbalance is exhausting for the one who’s doing all the driving.

Some people are just naturally passive though because they get anxious when making a choice. How about you let them plan what you’ll do on the fifth date to find out and and for all.

If they didn’t prepare anything even if you made sure all your four dates went well, then they’re probably passive in their relationship, and probably in life in general.

15) How you feel towards them

By the fifth date, you should know how you feel towards them. No extensions. It should be crystal clear to you.

First, ask yourself if you’re truly comfortable with each other.

Some awkwardness is to be expected in your first few dates, as you would be trying to know each other better then. But by the fifth date, you should already be somewhat comfortable with each other.

That is to say, conversation should flow well and not feel forced or rehearsed. Any silence between the two of you should be comfortable, rather than awkward.

Five dates are probably not enough to get you feeling completely at home with them. But you shouldn’t be busy trying to find the right thing to say!

Of course, it doesn’t mean that you should be able to tell for sure if they are your soulmate. It doesn’t mean that you should be able to tell whether you should marry them or not.

But you should at least know that they have a potential to be those things, and you can know that by going inward, by asking yourself how you truly feel towards them.

Are you in love? Do you think you have the potential to be really good together? Are you willing to do anything for them because you haven’t felt this strongly to anyone else before?

Or, do you think they’re awesome but they’re just not what you’re looking for?

Last Words

The first two or so dates are when you try to see if you agree in broad, yet shallow strokes. But by the fifth date, you should have known enough of each other that you can begin asking the hard questions.

After you learned what you have to know about them and you’re still not sure whether or not you like them enough to be in a relationship with them, then it’s clearly a “no”.

It’s the fifth date! If you still don’t feel strongly about someone by date number five, it’s probably time to let go.

It won’t happen. Stop forcing it, and don’t stay just because it’s “good enough.”

Date smart because you deserve the kind of love that will make your heart flutter.

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Lachlan Brown

I’m Lachlan Brown, the founder, and editor of Hack Spirit. I love writing practical articles that help others live a mindful and better life. I have a graduate degree in Psychology and I’ve spent the last 15 years reading and studying all I can about human psychology and practical ways to hack our mindsets. Check out my latest book on the Hidden Secrets of Buddhism and How it Saved My Life. If you want to get in touch with me, hit me up on Facebook or Twitter.

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