How to create a more engaging online conversation with a friend? [duplicate]

Question

I have a friend I talk with online and the conversations we are having are rather short. I would like to have more engaging conversations without forcing myself and the other person in a conversation we don't want.

Here an example of how the conversation is usually going, this happens when I start the conversation or when the other person starts the conversation. The conversation example is quite generic and the subject is always a little bit different.

Other: Hey, how are you doing?

Me(5 min to 1 hour later): hey, I'm doing okay, little bit busy with school. How are you doing?

Other(1 hour to 2 hours later): "something small about the day only responding about what I said, in this case busy with school".

Me(5 min to 30 min later): "responds talks about something small about the day"

Other(1 hour to 3 hours later): "short response" & I'm going to sleep, cya

Me(5 min to 30 min later): Okay good night

As the example shows, I response quite fast since I have my chat app open at all times, which means I see messages almost always immediately. The other person always takes more than an hour to respond.

For me this is quite though since I don't know how to respond. This also makes me quite unsure if this person wants to talk, however I think this person wants to talk since I'm not the only one who starts a conversation. I tried different things:

• Only asking about how their day was
• Saying something about my day (as the example, also in my first response)
• Responding to questions and not starting a new subject(to give the other person space to talk)
• Take more time to respond to messages, so I give more space

Question

How to start a more engaging, online conversation with a person who gives short responses and takes a longer to react to messages?

Goals

• Starting more engaging, online conversations with this person.
• Give the other room to talk about what they want to talk about.
• Not being clingy/codependent (I don't want this to be the focus of the question) however the distance should stay appropriate.

Notes

• I'm not the only one who starts the conversations
• We both are quite busy with school, however I'm not 24/7 working on it

Answer 1

Compatibility as friends and trust are really key here, I think.

Some of my most engaging conversations are with people that I trust, and these conversations last for several years. Here are some suggestions, based on my own experiences:

• Choose topics that are fun and gossip-y, e.g. who's dating who in your circle of friends, which professor is attractive and has a lot of admirers, what romance drama is unfolding around you two. When both of you trust each other enough to open up and gossip about things, the conversations really take on a life of their own, and it's really entertaining. Nothing is forced; it's a very organic process, but it starts with you two trusting each other and liking each other enough as friends.

• You can then choose topics that are more serious - topics that you both care deeply about (so that neither of you are bored and wants to cut the conversation short). Gender equality, racism, research goals, searching for a more meaningful life while at the same time balancing one's need to be able to afford basic needs -- these conversations between me and my friends are very lively and never ends. We don't run out of things to say and think about.

Regarding the timing of messages, you should give people enough room to respond - it's not uncommon for people to get back to me in a few hours, a few days, or even a couple of weeks -- time flies, when one is really busy with school or work.

Answer 2

Speak in terms of their interests, I've found How to Win Friends and Influence People helpful in engaging with people. But a conversation is a two way street in my option, others have to be willing to contribute to the conversation in order to keep it alive.

Answer 3

Online chat is probably not the best medium for building this friendship. If you don't hit it off on chat naturally, it's probably not worth it to keep trying to make chat work. One of the reasons people use chat is to have lots of short interactions without a lot of commitment to the conversation. You can multitask and chat throughout the day. If this isn't resulting in conversations that are meaningful, take it off chat. For this person, reserve online chat for basic logistical questions.

Instead, find meaningful experiences you can have. Meet for a meal, a drink, or an event. Talk to them on the phone.

Answer 4

Chatting i feel is only a stand in for real communication. I know i'm not REALLY answering your question, but all in all online chatting is for :

1. Setting up a meeting/outing.
2. Finding each other before the meeting
3. People who are unable to meet (eg. LDR)

Being personally engaged in no 3. I do have a few ways to engage with my GF over chat or calls since we're so far apart. This of course requires you to know more about the person and be closer to them in general. Also, try not to start a chat when it's during times like sleeping, work,classes. Times like lunch or mid-evening when people are winding down before sleeping would be a better time to engage in some online chats.

Try to ask more about what they mentioned, example :

Me : Hey, what's up?

O  : Nothing much, abit busy with school work , and you?

Me : work has been kinda slow recently, you got some big chemistry test coming up?

O  : nope, just some worksheets given out for English class.

Me : *more non-intruding questions about them while sharing bits of mine so it doesnt look like i'm interviewing them*

There we go, but if the person doesn't elaborate them i'm sure they ARE BUSY and are not in the mood for a extended chat. People try not to go full explanation right off the bat because they look very full of themselves. A little bit of question asking goes a long way.