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What To Do On Your First 5 Dates With Someone

Dating as a young adult can feel like walking a tight-rope.

In the modern culture of ‘Netflix and Chill’, you want to be intentional about actually getting to know the person you’re dating. But in a church culture where people start freaking out about finding their soulmate from age 22 onwards, you also want to keep things low pressure.

So, how do you find the balance? How do you date in a way that is both intentional and low-pressure?

Well, here’s how you could do it on your first 5 dates with someone:


The goal on your first date should be to create a low-pressure opportunity to get to know each other better. Trial and error (and error and error and error) has revealed to me that the ideal setting for accomplishing this aim is getting coffee together.

Why coffee? Well, going out for a 7-course degustation menu at the fanciest restaurant in town isn’t my definition of relaxed and low-pressure. Meeting up at the local café, on the other hand, is perfect.

Besides, you’ve successfully navigated grabbing coffee in everyday life many times before. You can definitely pull this off while in the presence of your potential future soulmate (woah, woah, woah – think low-pressure thoughts!).

If facing your date across a table while you sip your Unicorn Latte still seems daunting, no worries. Just order the coffee to go and take a stroll around the surrounding neighbourhood.

The other reason grabbing coffee is an ideal first date is because this particular activity goes for an indeterminate amount of time. If you go out for dinner, you’re locked in for at least an hour, minimum.

Not so with the casual cappuccino! Grabbing a coffee can last for 30 minutes or 4 hours.

If it’s not going well, no worries. Just announce that you “probably need to get going” and carry on with your day, emboldened by the double-choc-chip frappé that unfortunately ended up being the most enjoyable part of the last 30 minutes.

However, if your date is off to a great start, order another almond-milk latte and spend the next two hours bonding over your mutual love of nut-based milk products.


Congrats on making it to Date No.2! You’ve survived the inevitable awkwardness of working out how to greet your date for the first time and things obviously went well enough to merit a second date.

Your goal for this date should still be getting to know each other. Chances are, unless you were good friends prior to dating, you still know very little about the other person.

Even if you were good friends previously, there can be a lot of value in giving yourselves the chance get to know each other in this new context. My girlfriend and I had known each other for 9 years prior to dating, but on our first few dates everything felt very new and very different.

At this point, I’m all in favour of taking things up a notch and going out for a meal together. Yes, it’s a more formal setting, but by this point the two of you should know that you can carry a conversation for more than 30 minutes.

If things continue to go well, you’ll get a chance this evening to answer one of the truly soulmate defining questions: is he or she the type of person willing to share their dessert?


Time to stop staring into the other person’s eyes across a table and actually go do something. You want to find out what this person is like in different situations. Are they adventurous? Competitive? Artistic? A nature-lover? Unequivocally opposed to any form of physical activity?

The best way to find out is to embark on an activity together. Steer clear of going to the movies and instead do something that is going to encourage conversation – visit a museum, go on a hike, or play a round of mini-putt.

Typically, when you start dating, everyone is their own personal PR agent. We try to put forward the best, most-dateable, version of ourselves.

An activity is a great way to lower the faćade. It takes your focus away from trying to impress one another and directs attention towards whatever the two of you are doing, whether that’s ten-pin bowling or trying to understand ‘Man Screaming in a Room’, the latest performance art piece at your local gallery.


Up until this point, the two of you have been going out to do something. For your fourth date, change things up and stay in. Invite the other person over for a home-cooked meal or maybe an indoor picnic.

This can be a big step. Inviting someone in to your home allows that person to learn a lot about you and how you live. It also allows you to see your date in a more everyday setting.

For me, I’m usually at this point with someone by Date 4. If you aren’t, no problem. The whole idea is to get more comfortable. If the thought of having your date in your living room makes you decidedly uncomfortable, hold off.

While the five dates in this blog post follow a clear progression, in practice there’s no one-size-fits-all approach for dating. It might take you 10 dates before you feel comfortable to move on to Dates 4 and 5; it might take you 15.

There’s nothing wrong with that. One of the perks of Dates 1–3 is that you can keep going on different variations of those dates until you’re both ready to move forward.


As you start to think more about the prospects of a romantic relationship with the other person, Date 5 can be an opportunity to introduce something that is important to one/both of you.

For me, one way I’ve done this date is to meet up one morning and go to church together. Not only does this incorporate something important to me (my faith), you can follow it up with the most important meal of the day: brunch.

This is just one example. Others might be volunteering a day together at a local charity because helpings others is important to you, or organising a group activity where your date can meet some of the important people in your life: your friends.

If you do end up in a relationship, it’s going to be important that what matters to you also matters to your significant other.


By the end of Date 5, you’ve hopefully got a pretty good idea of whether you can see yourself in a romantic relationship with the other person or not. You’re on your own from here!

For Date 6 and beyond, the best advice I can give is to keep being intentional. As you get more comfortable with someone, it’s easy to let your intentionality slip. You get to Date 15 and laziness starts to creep in.

Maybe it takes the form of inviting your boyfriend/girlfriend over to watch The Office for the third date in a row. Maybe it takes the form of “just having fun” on dates without making an effort to gradually go deeper in your relationship.

If you start to notice this in your relationship, renew your intentionality. Be creative when planning dates, do things you haven’t done before, and look to create opportunities where the two of you can get to know each other better.

Finally, don’t stop dating. I’ve been with my girlfriend for over a year and we still look forward to date nights every week. I know couples who have been married for 20 years and dating is still an important part of their relationship.

Your first five dates are hopefully just the beginning.

Think you’ve got a better idea for Dates 1–5? I’d love to hear it in the comment section below!

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2 People Replies to “What To Do On Your First 5 Dates With Someone”

  1. Roney Mac

    Great article with practical suggestions!

    1. Thanks Roney, I’m glad you thought so!

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