Message Sutra: How to approach someone on Whatsapp

Whatsapp is one of the most popular communication apps that has an entirely different conversation culture and messaging manners. If you want to know how to approach someone on Whatsapp, think about how you would ask that person if it was a face to face chat. Be genuine, confident and always be courteous in the words you use in chat on WhatsApp.

Having a good conversation is the key to making the other person reply to you. Ask questions to show her that you care about getting to know her, and find a topic that’s close to her heart. Try to relax, be yourself, and remember that the best way to impress someone is by not trying too hard.

It’s not easy to ask questions especially when you don’t have any idea about each other. If you are new to this type of chatting, you may find some conversation starters useful.

Memorize some conversation starters

Here are several examples of good conversation starters on various topics.

Light conversation starters

• Do you like [celebrity names]?
• What brought you to Whatsapp?
• Do you know [your favourite thing to do or hobby ]?
• Where are you from?
• I like your [part of the outfit in profile], where did you get it?
• I believe we met before at [place where you met before]?
• Hello, my name is [name]. What’s your name?

Food conversation starters

• Have you tried the [dish]?
• What’s your favourite type of cuisine?
• If you opened a restaurant, what kind of place would it be?
• What’s the most exotic thing you’ve ever eaten?
• What’s your favourite comfort food?
• Are you a keen cook?
• What’s the worst thing you’ve ever eaten?

Work conversation starters

• What department do you work in?
• What projects have you been working on recently?
• Where did you work before you started this job?
• What do you like most about working [company or place of work]?
• Did you have to relocate for this job?
• How do you handle stress when work gets busy?
• I think the company’s new policy on [whatever the policy is about] is [give your opinion]. What do you think?

Group conversation starters

When you join a group conversation, avoid rehearsed conversation starters. Instead, listen in on what people are already talking about and contribute to the ongoing conversation. With that said, there are times where a topic dies out. Here are some ideas for how to start a new interesting group conversation.

• Have you heard the news about [news story]?
• Have any of you seen [recent movie release]? What did you think of it?
• What does everyone think of [latest episode of popular TV show]?
• Has anyone heard the new album by [artist]?
• Have any of you met before?
• What’s everyone’s dream vacation?

Conversation starters for expressing interest

• What’s your favourite thing to do when you have a day off work?
• What’s your family like?
• Do you have any cool hidden talents?
• When did you last go to the movies?
• Do you have a bucket list? What’s on it?
• When you and your best friend hang out, what do you like to do?
• When was the last time you felt really proud of yourself?

Conversation starters for friends

• How’s it going with [something you’ve talked about before]?
• What’s your favourite memory?
• Would you ever like to be famous? If so, what would you like to be famous for?
• Do you ever think about what you’ll do when you retire?
• Have you ever been so embarrassed that you wanted the ground to swallow you up?
• When do you think we’ll be able to take day trips into space?
• Have you ever wanted to keep a rare or exotic pet, like a tarantula?

Simple day-to-day Whatsapp conversations

Ask about day-to-day situations where you might want to strike up a conversation. Don’t ask direct questions about his or her day-to-day life, just simple questions about the situation rather than the other person.

To ease into a conversation, ask a question or an opinion about the situation you are in. It helps to ask something that you already have on your mind. But if you don’t, you can use your surroundings or the situation for inspiration.

Take this situation as an example of a story that you can use in your day-to-day conversation.

‘Last week I ended up next to someone on the train. I’d been wondering if they served snacks on board. It was a natural conversation starter because it was already on my mind and related directly to my surroundings.

I asked her, ‘Excuse me, do you know if they serve snacks here?’

She responded with something like, ‘Hmm. Yeah, they should!’

Know that you don’t have to be clever. You don’t need to ask a deep or meaningful question. What you actually ask isn’t important when you approach someone on Whatsapp. You don’t have to try to come off as unique or smart in your first interaction. The best conversation starters are usually simple.

Asking a question is a way to signal that you’re friendly and open to social interaction.

Just like in real life, small talk on Whatsapp is often mundane and people are usually ok with that. Short messages are just warm-ups for more interesting conversation.

Keep the communication going

It’s normal to just get a short ‘yes’ or ‘no’ answer to your first question. It doesn’t mean that the person doesn’t want to message you back. Just give the person a few seconds to switch over to ‘social mode.’

But if they only give short answers to your follow-up questions, it’s usually a good idea to say ‘Thanks’ or ‘Nice chatting with you’ and move on.

Ask follow-up questions to signal that you’re interested in talking to someone.

In the example with the train, the question ‘Do you take this train often?’ is a simple follow-up to the first question about whether there were snacks available onboard.

Rather than asking a series of general questions like, ‘Where are you from?,’ ‘How do you know people here?,’ and ‘What do you do?’ you can use follow-up questions to dig deeper.

Take this conversation example:

You could ask, ‘Where are you from?’ followed by, ‘What was it like growing up there?’ and then, ‘What do you miss the most about it?’

Digging into a subject like this rather than asking shallow questions tends to make the conversation more interesting.

Mix asking questions with sharing about yourself

You don’t want to ask too many questions in a row or talk too much about yourself. So how do you find the balance? 

Use the Inquire-Follow-up-Relate (IFR) method.

Inquire: Ask a sincere question

Follow up: Ask a follow-up question

Relate: Share a little bit about yourself that relates to what they said

You can then start the loop again by asking a new sincere question by inquiring.

Take this conversation example that you can use as a story on Whatsapp.

‘The other day I was talking to someone who turned out to be a filmmaker. Here’s how the conversation went:

Inquire

Me: What kind of documentaries do you do?

She: Right now, I’m doing a movie on bodegas in New York City.

Me: Oh, interesting. What’s your takeaway so far?

She: That almost all bodegas seem to have cats!

Relate

Me: Haha, I’ve noticed that. The one next to where I live has a cat who always sits on the counter.

Repeat

Me: Are you a cat person?

You want to make the conversation go back and forth. They talk a little bit about themselves, you talk about yourself, then let them talk again and so on.

Types of questions

When to use open-ended questions

An open-ended question is a question that requires more than a ‘Yes’ or ‘No’ in response. By using open-ended questions, people often feel inspired to give a longer answer.

Examples of open-ended questions:

• What was school like for you?
• What sort of things do you do at work?
• What would your ideal vacation be like?

When to use closed-ended questions

However, this doesn’t mean that closed-ended questions are bad. For example, if you initiate a conversation in day-to-day life, an open-ended question can feel too abrupt, while a close-ended question is more natural:

For example, ‘Are you done reading that magazine?’ is more natural than ‘What did you think of that magazine?’

Examples of closed-ended questions:

• Did you like school?
• What’s your job title?
• Are you going to take a vacation this year?

Tone and word choice

The tone in the words you use is important in Whatsapp. The impression you make on someone on Whatsapp depends partly on what you say, but it mainly depends on how you say it. Many people focus too much on what to say rather than their delivery.

You want to sound friendly and in a relaxed tone of voice. If you can do that then you don’t have to worry about the exact words you use. You don’t need to be overly confident to sound friendly and relaxed. 

Practice by reading your messages aloud to yourself first before sending them. When you send messages on Whatsapp, always think about how you would say it in person in a courteous manner.