Rules for Keeping a Conversation Interesting

boring conversation glasses

Just because my profile said I like cats doesn’t mean we can ONLY talk about cats.

Ok, it wasn’t cats. It was Mystery Science Theater 3000. And technically my profile didn’t say I liked it. Just that I talk through movies LIKE in MST3K. I think you get what I’m saying here though.

I had this guy message me about the reference to Mystery Science Theater 3000. Allow me to first illustrate how that reference is made in my profile:


We did progress to an actual in person date after a few days of talking. During this date, he spent the entire time talking about MST3K. I have seen episodes of the show and do find it funny, but I’m not the world’s biggest fan. Nor do I claim to be. If you look at my profile, I compare my incessant chatter during movies to be LIKE the show concept of making snarky comments and observations.

It was the longest, most boring, painful date I had been on in a long time. Whenever I attempted to deviate conversation to anything else – he would bring it right back around to the show. For a little bit, he did tangent into all of the events he goes to for comics and video games (I’m not talking geeky chic Comic Con either here – more hard core nerd-fest).

By the end of the night, it was clear to me that we were not a match. I thanked him for a nice night and took myself home.

A few days later, he asked if I would like to go out again. I politely told him that I didn’t feel like it was a good match and did not want to continue moving things forward. His response, “I thought we had so much in common.” I had to take a moment and explain to him that what he was most passionate about was just not a shared interest for me.

Initial conversation for first dates can be tough, especially when you meet online. It can be hard to figure out what to talk about and keep conversation fluid for the evening. You don’t have any common friends or things to refer to from meeting in real-life before committing to a date. But there are ways to help avoid a completely boring night for either person.

For quality conversation during a date:

  • Vary the conversation. Don’t stay on one topic too long. The goal is to get to know your date’s interests. If you stick with one topic for the entire evening, you really don’t get to learn much. People are multi-dimensional and will like more than one thing. Natural conversation will tangent and lead to new topics – let that happen!
  • Read their profile for interests. Actually pay attention to how things are listed though. In my case, all this guy saw was MST3K, ignoring that it was a reference to how I talk during movies. Most people will list a few different things under a “favorites” section. Go ahead and take a look at those.
  • Not every interest must be a shared interest. Conversation is best when there is an element of opposition. If your date listed an interest that you don’t know much about, that’s a great way to get them to open up. If your date lists something that you hate, that’s an opportunity for a healthy debate.

Holding a conversation is not always easy. But if both parties try their best to listen to each other and not stress too much about staying on script and with a particular topic, you’ll probably end up having a good time.

2 thoughts on “Rules for Keeping a Conversation Interesting

  1. Pingback: Chemistry Fail | Single Chicks Blog

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