Conversational Pre-Work

Overview

The techniques in this article that I will discuss are not just limited to romantic settings or even just for getting to know someone new, it can be used in any social situation where you want to have things to talk about in your back pocket.

I call these techniques “conversational pre-work”, and while it may seem a bit silly to prepare for conversations, I think it can allow you to feel more comfortable in conversation, which in turn will allow you to demonstrate more of your personality. These techniques are all aligned to a particular question/type of question, but you can certainly adapt these techniques in other ways to work on questions that they were not designed for/that I couldn’t anticipate.

Why prepare to make good conversation?

An important thing to note is that this isn’t about lying or faking charisma, it is about being prepared so you don’t fumble the beginning/basics in order to create conversational doors to create moments of connection with another person.

Making a conversation seem natural is about being able to transition to new topics gracefully. In my opinion, this means following all tangents, but guiding back to the main conversational thread, which should be getting to know each other more directly through questions and answers. If a topic ends, just start a new one, it doesn’t even have to be related to the previous discussion.

If conversation is a lot of silence, it might mean that the other person just isn’t a good conversationalist. This is fine, but it is something to note if you want to continue meeting with this person. Keep an eye out for how many questions they ask and if they freely volunteer information and bring their own curiosity and vulnerability to the conversation.

How are you? How has your week been? How was your weekend?

These are seemingly harmless/easy questions and you can answer them phatically (“Oh you know, good. What about you?”) or you can try to meaningfully engage with them.

Technique: Look back at your calendar and think of at least one good story.
This way you can show that you do interesting things and/or have close friends. It can also serve as a great conversational jump-off point.

Starting off strong with an answer to this question can set the tone for the rest of the conversation. The story doesn’t even have to be that long, it just has to have enough information for someone to comment on an aspect of it.

What have you read, watched, listened to recently?

This is another common question that is actually quite hard to answer in the moment, especially if you have a bad memory. This is something that is very easy to prepare for, but also this is something where I generally find it acceptable to scroll through your phone during the date to show things to the other person.

Technique: Look back at your Goodreads, Letterboxd, Spotify, etc. to see what you have consumed/liked recently.
Media/art is one of the best ways to get to know someone and recommending something to someone is a powerful way to get closer.

You could also talk about an article, YouTube video, the news, really anything that offers an interesting springboard for conversation. I do think it is important to have some kind of personal resonance to the piece of content or at least some kind of critical thoughts about it so that it is more than just “I read this thing recently, it was very interesting.”

Tell me about yourself.

This question doesn’t always get asked explicitly like this, but a date (especially a first one) in essence is all about getting to know someone. For each thing you volunteer about yourself, you should also want to get the other person’s symmetric information. Obviously you shouldn’t except them to match detail, especially if some things are more vulnerable/intimate. You want to talk about equal because you want to show who you are, but you also need to know who the other person is.

You can have a little elevator pitch about yourself if you want to, but I personally prefer a more turn-based questions approach.

Technique: A good framework to use is FORD (Family, Occupation, Recreation, Dreams).
This allows you to generally talk about your own past, present, and future and should cover most (if not all) of what you need to know about someone.

FORD is an mnemonic acronym which means that the order of the letters only matters because it is easier to remember. You can go in any order you prefer and you don’t need to use all of them if you don’t want to.

A breakdown of FORD, with some example questions:

• Family
  • Ethnicity
  • Siblings + Birth Order + Closeness
  • Family Occupations
  • How Parents Met
• Occupation
  • What do I do at work?
    • Short summary of work (non-technical terms)
  • What do I like about work? Not like?
  • Where else have I worked?
• Recreation
  • What are my hobbies?
  • What kind of media do I like to consume?
• Dreams
  • What do I want for my future?
    • What do I want to be doing?
    • Where do I want to be living?
    • What kind of relationships do I want to have?
  • What would I do if money wasn’t a concern?

The above FORD details about yourself don’t really change much, so I think having a note in your phone where you go down the list and answer all the questions to internalize a narrative about yourself can be helpful. You shouldn’t memorize it in whole though, because I think that can lead you to sound too rehearsed. There is also a lot of give and take in conversations about getting to know someone, so in memorizing it you would have to also keep track of spots to ask questions of the other person.