I need advice on how to keep Conversations going!



Protorum asks: 

I need a little help with keeping up a conversation. I met a girl on the train and I saw her every morning for the last week. We looked at each other and smiled for a while and 3 days ago I decided to talk to her. Since I walk to her every morning and text her. The only problem is, after things like work and telling her about my hobbies, I don’t know what else to talk about. She doesn’t ask questions and answers mine with short answers. I tried to ask her about her hobbies, but after work she is really late home and doesn’t do anything, as she says it. And when I asked her, what she does at the weekend she only said she goes out.

I know that she’s into me, because a friend of mine knows her and I want to learn more about her. But what I don’t know is how I can keep the conversation going for more than 10 minutes.

If you have any helpful tips, it would be nice to know.

Demetrius says:

I do have helpful tips! That’s kind of my thing, so I’ll give them to you with aplomb. First, some general advice on the situation you’re in. I’m glad that you know through a secondhand source that she is attracted to you, or at minimum enjoys conversation with you. People who aren’t conversationalists often exhibit the same patterns and behaviors that someone who is not interested in you might exhibit (lack of responsiveness, disinterest, brief answers, etc.). I’ve met so many people who I thought weren’t interested in having a conversation with me because they just weren’t good at small talk. I got better at recognizing the difference between disinterest and disiniterest in small talk by getting better at reading body language. In the future if you’re in a similar situation but don’t have the luxury of a friend saying “No dude, she’s totally into you” try to read the body language of people who seem disinterested. For the most part, if they aren’t the best at small talk but are giving you positive body language, proceed. If they aren’t responsive and seem to be expressing body language that screams “I AM CLOSED OFF” move on. Now, on to those tips.

I’ve found that people who aren’t good at small talk, don’t enjoy small talk, or are not big on talking in general will get better at talking about the things that they are passionate about. Lucky for you, you share a mutual friend. Hit that mutual friend up for info on what exactly she’s passionate about. It’s entirely possible that she’s one of those people who doesn’t have interests outside of working late and partying, but I doubt it. I spoke about this in a recent post, I think that some people need a bit of time to warm up to conversation to relative strangers. In your case, you might want to find out what interests she has and ask her about them. It will be hard to do because she seems to be a very terse speaker, but it’s not impossible. You can ask your mutual friend as I mentioned before or you could take it a step further and do some research. Sorry if this sounds weird but I’m 100% on board with a little bit of social media searching when it comes to dating. If you are struggling for what to talk about with someone, try googling them and seeing what you find. Maybe her instagram page is full of pictures with a common theme like say, street art, or cute dogs, or I dunno, mirrors in the East Village. Whatever it is, whatever you find (that isn’t embarrassing of course) bring it up. You don’t have to lead with “I saw on social media that you like x” you can just bring it up. You don’t have to bring up the exact thing, you can always bring up a related topic. Example for you: She posts constantly about her love of food or restaurants, you ask her if she’s been to a restaurant you love. It’s as simple as that.

If you’re still struggling with conversation, you have to ask questions and bring up topics in a way that cannot be answered with short answers. Asking someone what they did over the weekend is good, but if all you’re getting is “Nothing much” and a shrug, you’ve got to change your tactics. Ask questions that requires an opinion. Asking her how work has been going is a great place to start. Chances are she’ll say something along the lines of good, bad, or give you an indifferent response. This is a good start, believe it or not. You’ll then want to follow this up with a question about how she feels. If work has sucked lately, ask why that is. If she still seems unresponsive, or if your line of questioning isn’t leading to much, change the topic, but remember to ask questions that lead to conversation, not answers. What was the last movie she saw, and how did she feel about it? When was the last time she saw something online she found funny? You get the idea. If you ask a question that requires more than just a one word response, she’ll start to open up a bit more. That’s the hope at least.

One other thing,  although I’ve been positive through all the advice above, I’m going to throw some doubt your way. You need to ask yourself if trying this hard to have a conversation with her is worth it. It’s for you to decide, there is no right or wrong answer here, but it’s something to think about. Just because she’s attractive and nice and is interested in you doesn’t mean you have to date her. Maybe she’ll warm up eventually, but it will probably take a bit of work so you have to figure out if that work is worth it. I’m a big fan of equality in dating, especially when it comes to effort so I’d probably avoid dating someone where I was putting in a lot of effort to talk to them, but was giving me nothing in return. That’s just me, and I know that a lot of men have this drive to date women who are difficult to date, so maybe you’re one of those guys. Whatever you decide, just know that you are making a choice. Right now you like this person on a very surface level, so you need to really give some thought into whether or not pursuing her is worth the effort.

Remember, no wrong answers, I would just encourage you to make an informed decision.

Good Luck Out There.

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