How Should Your First 5 Dates Look? A Guide for Indian Singles in Their 20s and 30s
If you are in your late 20s, 30s or 40s, there is a good chance you have already been on at least one or two dates.
And if you haven't, that's completely fine too.
You may have just started dating and are wondering: What are you actually supposed to do on the first few dates? How long should a first date last? What should you talk about? Should you go for coffee, lunch or dinner? And how do you know if you should meet the person again?
There is no dating rulebook. But after speaking to and guiding many Indian singles who are dating with the intention of finding a long-term partner, we at andwemet have noticed that the traditional way of dating can sometimes make the process unnecessarily exhausting.
The problem with the traditional first date
Traditionally, a first date often means meeting over coffee, lunch or dinner.
It can last anywhere between 45 and 90 minutes, sometimes even a couple of hours.
And after all that time, you can walk away thinking:
"What did I actually learn about this person?"
You may remember a lot of information.
Where they grew up.
Where they studied.
Their previous relationship.
Their job.
Their family.
Where they have travelled.
And you may have shared just as much about yourself.
But these are mostly data points.
And they don't necessarily tell you whether you actually enjoy being around this person.
Especially when you don't even know whether you will meet them again.
Now imagine doing this 20, 30 or even 50 times.
It becomes exhausting.
You may not even be enjoying the conversation, but you feel obliged to sit there because you have already ordered the food and don't want to be rude.
You are essentially spending 90 minutes trying to keep a conversation going with a stranger because you think that is what a first date is supposed to look like.
We think there is a better way.
What if your first 5 dates were about getting to know someone, not interviewing them?
At andwemet, we believe dating should be about experiencing someone, not just collecting information about them.
The first few dates don't have to feel like interviews.
You don't have to decide on the first date whether this is the person you will marry.
You don't have to discuss your entire past, present and future in one evening.
And you certainly don't have to force a two-hour conversation simply because you are sitting across a table.
Instead, think of the first five dates as five opportunities to see how you feel around each other.
Do you have fun together?
Are you comfortable with each other?
Can you be yourself?
Do you enjoy their company?
Do you like them as a person?
Does the conversation happen naturally?
Do you want to see them again?
These are far more useful questions in the early stages of dating.
So here is how we at andwemet would approach the first five dates for Indian singles in their 20s and 30s. You can do the same activity again and again for all 5 dates or add a variation.
1. Keep the first date short
If you want to meet over coffee, tea or lemonade, that's absolutely fine.
But keep it to around 30 minutes.
Yes, 30 minutes.
You are not finalising anything.
There is no reason to rush into a long conversation with someone you have never met before.
A short first meeting gives both people an easy exit if there is no connection.
And if you genuinely enjoy the conversation?
You can always meet again.
Why we don't recommend lunch or dinner for the first date
Lunch and dinner can easily turn into a 60 to 120-minute commitment.
Once you have ordered food, you are more or less committed to sitting there.
If the conversation isn't flowing, those minutes can feel very long.
You may find yourself thinking:
"How do I get out of this without being rude?"
That's not how a first date should feel.
Our preference: meet briefly, see how you feel, and leave wanting to know more rather than feeling exhausted.
2. Try an activity instead of sitting across a table
This is one of our favourite ways to meet someone.
Go for a walk.
Play badminton.
Try a racket sport.
Go cycling.
Go for a run.
Try a beginner-friendly activity together.
The activity itself isn't important.
The interaction is.
An activity takes some of the pressure away from having to constantly talk.
You aren't sitting in a confined space staring at each other trying to think of the next question.
There is something else happening around you.
And when there is an awkward silence, you don't have to panic.
You can simply continue playing.
It also makes the date more relaxed.
You don't necessarily have to dress up.
You get to see how the person behaves when they are having fun, losing a game, winning a game, getting competitive or trying something new.
And there is another advantage.
You get some movement into your day instead of spending every date sitting across a table.
Remember you don't have to be good at the activity
This is important.
The goal isn't to impress the other person with your sporting abilities.
You don't need to be a marathon runner or a badminton champion.
The goal is to have fun together.
When you are relaxed, you behave more naturally.
And when both people are behaving naturally, you get a much better sense of who you are actually getting to know.
You can always follow the activity with a short coffee or plan another activity for your next meeting.
3. Explore something together
Visit a museum.
Explore a craft bazaar.
Go to a planetarium.
Visit an exhibition.
Walk through a bookshop.
Explore a neighbourhood you haven't spent much time in.
The advantage of doing something like this is that the focus isn't entirely on each other.
You have something to look at, discuss and experience together.
You can observe the person without constantly asking questions.
What catches their attention?
What are they curious about?
Do they notice things around them?
Are they interested in learning something new?
How do they treat people they interact with?
Do they listen when you are sharing something?
Sometimes you learn more about a person by observing them than by asking them a list of questions.
4. Play a board game together
A board game café or a simple game you both enjoy can make for a surprisingly good date.
Yes, you are sitting across from each other.
But the focus isn't entirely on the conversation.
It is on the game.
And that gives you something to do together.
You may laugh.
You may get competitive.
You may disagree about a rule.
You may discover that one of you absolutely hates losing.
And that's useful information too.
You are getting to see someone's personality in a more natural environment.
How does someone behave when things don't go their way?
That's often much more revealing than asking:
"How do you handle conflict?"
By the fifth date, ask yourself a different question
By now, you have hopefully spent time together in different situations.
You've talked.
You've played.
You've walked.
You've explored something.
You've laughed.
You've experienced some awkward moments.
And perhaps you've even disagreed about something.
Now ask yourself:
"Do I actually enjoy this person's company?"
Not:
"Is this the person I am going to marry?"
Not:
"Are they perfect?"
Not:
"Do they tick every box?"
And definitely not:
"What will my parents think?"
Just:
Do I enjoy being around this person?
Do I look forward to meeting them?
Can I be myself around them?
Do I feel comfortable?
Do I like the way they communicate?
Do I respect them?
Do I want to know them better?
Do I like them as a friend?
Because if you are looking for a long-term relationship, friendship matters. A lot.
The first 5 dates are not about deciding your future
This is perhaps the most important thing we would like you to take away from this.
When you meet someone for the first time, don't assume they are going to be your life partner.
That assumption can put enormous pressure on both of you.
Instead, think:
"I am meeting this person to understand whether I enjoy knowing them."
That's it.
You don't have to evaluate their entire personality in 60 minutes.
You don't have to decide whether they are "the one."
You don't have to interrogate them about their five-year plan.
You don't have to bring every expectation you have about marriage into the first meeting.
Give yourself permission to simply get to know another human being.
When the pressure comes down, the judgement often comes down with it.
And when judgement comes down, curiosity has room to grow.
Should you talk about marriage and serious relationships in the first five dates?
If you are dating in your late 20s, 30s or 40s with the intention of finding a long-term partner, you should not hide your intentions.
But there is a difference between being clear about what you want and turning the first date into a marriage interview.
You can say that you are dating with the intention of finding a committed relationship.
You don't need to immediately establish whether this person is going to be your husband or wife.
As you continue meeting, conversations can naturally become deeper.
You can eventually discuss:
Marriage and long-term commitment
Children and parenting
Where you want to live
Career ambitions
Financial expectations
Family responsibilities
Lifestyle preferences
Previous relationships
Emotional availability
What a healthy relationship looks like to you
The timing will vary from person to person.
The important thing is that serious conversations should happen before serious commitment, not necessarily before the first coffee.
And one dating rule we strongly recommend: split the bill
Here's an andwemet dating rule we would love more people to follow:
Split the bill.
Both people are investing time and effort into getting to know each other.
Splitting the check keeps that investment equal and removes unnecessary expectations.
If you genuinely want to treat the other person, you can always do that later.
Perhaps on the fourth or fifth date you can say:
"This one's my treat."
And then let it be a gesture rather than an expectation.
What should you really be looking for in the first 5 dates?
Not perfection.
Not a checklist.
Not whether someone looks like the person you imagined.
Instead, look for comfort, curiosity, friendship and compatibility.
Pay attention to how you feel around them.
Do you feel safe enough to be yourself?
Do you enjoy your time together?
Can you communicate when something feels uncomfortable?
Do you feel heard?
Are you curious about each other's lives?
Can you have fun together?
Can you disagree without the entire interaction falling apart?
These things may tell you far more about your potential together than how impressive someone's dating profile looked.
What if there is no chemistry?
That's okay.
Not every person you meet is going to become a partner.
Some people may become friends.
Some connections may end after one date.
Some may last five dates and then naturally stop.
And occasionally, someone who didn't create fireworks on the first date may become someone you genuinely care about after spending more time together.
You don't always need instant chemistry to explore a connection.
Sometimes comfort, curiosity and friendship need a little time to develop.
Dating should feel like getting to know someone, not completing a checklist
If you are dating in your 20s or 30s, being Indian where there can already be considerable pressure around marriage, it is easy to approach every new person with the question:
"Could this be my life partner?"
Try replacing that question with:
"Do I want to know this person better?"
That one change can make dating feel very different.
Your first five dates don't need to determine your future.
They simply need to help you understand whether there is enough comfort, curiosity, friendship and compatibility to have a sixth.
And if there is?
Go on that sixth date.
Keep getting to know each other.
Because a happy, healthy long-term relationship isn't just about finding someone you can commit to.
It is about finding someone you like being with, respect, trust, enjoy and continue choosing even after the dating phase is over.
And perhaps that is what dating should really be about.
**Not finding "the one" in five dates.
Finding out whether you would like to know this one person a little better.**
Frequently Asked Questions About the First 5 Dates
What should the first five dates look like?
The first five dates don't need to follow a fixed formula. It's how you want it - approach is to use different settings and activities to understand how comfortable you are together or do the same activity again and again . You could start with activity, an outing such as a museum or craft bazaar, a board game, and then a more intentional conversation about whether you both want to continue dating.
How long should a first date last?
A first date can be as short as 30 minutes, especially when meeting someone for the first time. A shorter first meeting gives both people the freedom to leave if there isn't a connection without feeling trapped in a long meal.
Is dinner a good idea for a first date?
Dinner is best if avoided, it isn't our preferred option for a first date. A meal can create a commitment of 60 to 120 minutes even when two people realise early that they aren't compatible. A short coffee, tea, lemonade or activity can create less pressure.
What should you talk about on the first few dates?
You don't need to cover your entire past, present and future on the first date. Start with everyday life, interests, experiences and things you genuinely enjoy discussing. As you continue meeting, conversations can gradually move towards values, relationships, family, children, finances, lifestyle and long-term expectations.
Should you talk about marriage in the first few dates?
If you are dating with the intention of finding a long-term relationship, it is healthy to be clear about your intentions. However, you don't need to treat the first date like a marriage interview. Serious conversations can become deeper as mutual interest and comfort develop.
How do you know if you should go on a sixth date?
Ask yourself whether you enjoy this person's company, feel comfortable around them, respect them, enjoy talking to them and are curious to know them better. You don't need to know whether they are your future spouse. You only need to know whether you want to continue exploring the connection.
Should you split the bill on a first date?
At andwemet, we recommend splitting the bill because both people are investing equally in getting to know each other. If you want to treat the other person, it can be a thoughtful gesture later once you know each other better.
Do you need chemistry/vibe on the first date?
Not necessarily. Some connections develop slowly. While attraction and chemistry matter, comfort, curiosity, friendship and compatibility can also grow with time. The first date doesn't need to provide a definitive answer about the future.
What is the purpose of the first five dates?
The purpose of the first five dates is to understand whether you enjoy spending time with someone and want to know them better. They are an opportunity to observe compatibility, communication, comfort and personality without putting the pressure of deciding your entire future on the first meeting. Need help to learn more, schedule an interaction with us of guidance/ clarity.
