The Speed Dater: Becoming a better conversationalist (Intro)

Hello again,

After meeting someone and engaging them in smalltalk, the next step is to deepen the conversation to establish solid rapport and find out if the person across from you really is someone you want to invest your time and affection in. Some underestimate the importance of this middle step in dating, but for me it's a must - deep conversation lets me know if a girl is worthy, and generally helps me weed out the crazies before it's too late.

Case in point, I was in the car with my friend "Seth" (a girl told him he looks like Seth Cohen from "The OC") when he brought up the topic. He does very well for himself but dislikes going on dates because he is not the best at making conversation (that's okay, especially if he realizes it and decides to work on improving that aspect). So I decided to show him the lesson you're about to learn today.

Now, the first thing you should understand is that most people are selfish. I don't think it's a particularly bad thing, but that could just be the only child in me talking. The upshot is, that for the vast majority of people you meet, men or women, young or old, the topic of conversation that most interests them is, well, themselves. You might not care that I sat next to a smelly hobo in the metro today, or that I had mild BBQ flavored chicken wings for dinner, or that my prof is a tool who doesn't know the first thing about how to crack a decent joke, but I sure do. And if you want to get my attention, I hope you are willing to let me talk about these things (and at least PRETEND to give a damn). In any case, rest assured that letting them decide what they want to talk about is usually the best course of action. (There are exception, as we'll see later)
If you like talking about yourself too much, that's okay also, just refrain around people who you want to actually be attracted to you...


Once you got the first part down pat (let the other person talk), comes part 2: letting the other person talk about something meaningful to them. Meaningful topics vary from people to people, it's up to you to find out. Anything goes, as long as it doesn't fall into one of the following categories:

1) Fluff
2) Complaints


Fluff (or "smalltalk) is completely fine if you're 30 seconds into a conversation and as long as you're using it as a jump-off point for deeper, more captivating topics. Relying too much on fluff is bad, for the following reasons:

1) You will run out of things to say (you'll always be scrambling mentally to find the next thing to talk about, which is really difficult. Plus your listening abilities go to the crapper if your mind is that occupied)
2a) You will find yourself talking to your date about boring topics
2b) Your date will take it as a sign that, since you talk about boring trivialities, you must be a boring person. (Even if you're not)
3) Since no one likes to be bored, your date will find a way to wiggle him/herself out of your next meeting, and the next, and so forth.

How to avoid this? Let's go back to the car ride with Seth for one second:

Him: I always run out of things to say. I suck on dates 'cause I just don't know what to do after a while.
THM: Let's try something really simple. What was the first career you wanted to have when you were little?
Him: Uhh....to be a doctor.
THM: Why?
Him: I don't know. After high school I realized that science wasn't for me, so I want to do international development (talk about that in more detail for 5 more minutes).
THM: Interesting. Actually it's not so far from being a doctor. I see you're motivated by helping people, and both jobs let you do that.
Him: Wow I never thought of it that way, but it does make sense... (another 5 minutes of him talking about why he wants to go into that field - at the time I couldn't make anything other than rough mental notes, sorry dude)

So you can see I've managed to turn something as mundane as school and work into an enlightening conversation (incidentally, I never knew Seth wanted to be a doctor before). There are lots of little things to pick up on, but essentially I turned something relatively impersonal (we were talking about something school-related) into a reflection about Seth's passions and driving forces in life (which is one of the most personal things we can talk about). Try it, and don't be afraid to ask a lot of "why" questions. Some people are more guarded then others, but the more barriers you can break down, the closer you'll be to that person's heart.



Complaints are a whole other can of worms. In the same way that people label you as boring if you allow them to talk about boring stuff, they will also label you negatively if you allow them to dump all their problems on you. Sure, commiserating about serious and important matters is a beautiful thing - that's what friends are for. But on the flip side, learn to not let your dates dwell on petty complaints (The soup's too cold. The soup's too hot, where's the waiter? Why do I always look so fat?) Don't enable serial complainers. Change the topic if it's really unimportant (avoid calling them on their negativity, just ignore it the best you can). Worst comes to worst, don't hang out with people like that. You owe it to yourself.

That's about it for today, talk to you soon.

Much love,
THM