So I've been a massive introvert for the larger portion of my life and I've finally started dating someone. Only the dates don't go too well.
Why? I suck at talking and holding regular conversations. Most of the conversations I tend to hold with my friends are either shop talk (uni work and computing), geek talk (gaming, TV shows etc.) and in-jokes (YOUR MUM talks about in-jokes) And in true geek style, they're not really conversations, are they? They're more like turn-based monologues.
So I do have some idea of what not to talk about (specifically, all of the above), but what do we talk about? How do you get a good convo going over the phone, and otherwise? What's a good way to open up a conversation?
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The most important thing is to listen. Listen to what they have to say and respond accordingly.
Try not to think too hard.
Read metafilter.com or D&D and use OP's as conversation fodder. I've done this successfully -- I was told I'd make a good dinner party guest! Learn about the different sides of a topical issue and throw it out there. "What do you think of this whole "Sexism cost Hillary the presidency" thing?"
Avoid interrogations. Ask about how they feel/think about about X Y Z but make sure you offer your position as well and give them room to comment. And be honest. Don't be 100% agreeable - engaging in a diplomatic disagreement might not be a good idea early on, but philosophical differences can add some flavour!
Also, are you sure it's you who is making the conversation stop dead? A really good conversation often requires both parties to be engaged and interested in the topic at hand. Sometimes you have to ask your date about stuff they're interested in, but sometimes you just can't talk about it because it's boring as hell or you don't know enough about the topic to do anything but interrogate.
Every time you find yourself "talking shop" with anyone, try to change the topic. A friend of mine's boyfriend worked for IKEA for 10+ years. I used it as a topic of mutual connection when I first met him (Hey what about that crappy IKEA furniture!) but this wore thin quickly and we found we had little else to talk about.
If you're run through the standard issue topics (favourite bands, tv shows, favourite colours, what do you study, where do you work, how crazy is your family, mine is totally crazy) then maybe your date isn't the best conversationalist either, and you should maybe look forward to a quiet life together.
I do not condone this advice. I hate talking about myself. I hate being asked what my day was like. I am in a rat-race and I hate it. Let's talk about rainbowz.
I think most people like talking about things that are interesting. But the underlying sentiment, "show that you're interested", is right and this should come naturally if you like this person.
So yeah, give them opportunities to talk about themselves and show interest if they do, but don't pry.
Here's a suggestion that has always worked for me: go on dates in places that naturally offer topics for conversation. Zoos, museums, long walks in places with people and things to see. Instead of going to a restaurant, cook together (if either of you is even remotely proficient at it); I know I for one can talk about food and cooking forever. The cliched movie date is good too, because you can always fall back on talking about the movie. Just try to extend the conversation beyond the movie, talk about what you'd do if you had been the main character (doesn't matter if it's a tragic love story or a zombie movie) etc.