| A good conversationalist knows to balance listening, telling stories/interesting news, self-disclosure, and humor. If you learn to excel in all four areas, you shouldn't have much problem keeping a conversation going - even with a complete stranger.
You should have a few stories available in your mental database to whip out whenever there's silence or tension. However, you shouldn't just shoot them out in the beginning of a conversation. Think of them as your backup material.
Your three main staples should be listening, humor, and self-disclosure. After you've gone past the small-talk stage, you should really try to get her to talk about herself. Remember this one rule: "People's favorite topic of conversation is themselves." Almost everyone would rather share about their interests than hear about the interests of others. I used to be skeptical when I heard this, but it's true. I can easily get people to talk about themselves for 30 minutes without any break. We're a lot more self-absorbed than we'd like to think. Don't ask her simple questions like "What are your hobbies?" You'll be interrogating her, and it'll feel very forced. Instead, ask her questions that require a long and meaningful response, like "What are your plans for the future?" Her response will give you more topics with which to branch off of, and also prompt her to self-disclose about herself. It's important to REMEMBER what she says. Whenever the conversation starts to lose momentum, you can say, "So you mentioned *blank*. Why is that?"
Self-disclosure is very important to conversation, because it creates an emotional bond between the two people talking. When you cause the girl to self-disclose, she'll begin to feel closer with you. However, it's also very important that you do the same. Think of it as an exchange. She shared something intimate and personal with you, so you have to "pay" her back. Be careful not to go overboard - nothing TOO personal (e.g., "I got beat as a kid"). The intimate nature of the subject has to match with the comfort level you feel with the person. There has to be a gradual progression. Self-disclosure is VERY important. If neither of you self-disclose the entire date, you'll be at the same exact spot as when you started, and that's not good. Self-disclosure is also important in creating attraction, because you show that you have a lot in common with the girl. When you say things like, "I feel so connected to you. I never thought I'd find someone who understands me like this," it can have a very powerful effect (don't forget to kino and show IOI's).
Note: Self-disclosure and story-telling tend to overlap, because you're essentially telling a story about yourself. The stories that you should save for later are humorous, tension relieving ones that aren't necessarily related to yourself (e.g., "I know this one guy who..."). This isn't necessarily a rule, but you should try to get by without stories for as long as possible; otherwise, what are you going to say when things start to get quiet?
Note 2: Do NOT neg a girl when she self-discloses something to you. Topics of self-disclosure are usually sensitive subjects. If you neg her about it, you'll probably just end up offending her. Sometimes, girls will self-disclose something that they may not feel proud about. The best thing to do is pick out the positive aspects of it; don't insult or put down. Elevate the mood of the conversation. And whatever you do, don't give her advice of what she should have done differently. People hate that.
Humor is your last staple. Avoid telling any traditional JOKES (e.g., "Hey, did you hear about the..."). When you tell one of those, you force the girl to become a passive listener - she'll focus all her attention on what you're saying. If the joke falls flat, it reflects very negatively on you, since you vouched for the hilarity of the joke by telling it. You'll appear unfunny. I never EVER tell jokes when I'm around people. There's just too much risk of them not going over so well. Instead, try to use witty banter. Be able to twist words and make jokes based off what is being said. This makes the conversation much more interactive for her, and puts less pressure on each joke having to be pure comedy.
One type of humor I've used for years is "creating an absurd reality." Mystery actually mentions this in the Venusian Handbook, along with some examples, so I highly recommend you check it out. Basically, you verbally create an absurd situation, and place you and the girl in it. For instance, if the girl says, "I like sushi." Then you say, "We should totally go to Japan, and become master fishermen. We'll run a black market sushi ring, to help cover our overhead costs. We can eat all the sushi that we want. Eventually we can search for the mysterious Black Thundercod... "
It sounds stupid, but, believe me, the girl will laugh. In fact, she'll probably play along and start adding her own details. This creates a highly interactive experience for both of you, and helps to create an even stronger bond between you two. This type of humor doesn't require too much quick thinking. Just weave the story from whatever pops up in your head. Your brain will start throwing you words that logically connect. (e.g., sushi - Japan - fishermen). Even if they don't really connect, just throw them in there anyways. It'll add to the absurdity, which adds to the humor. The great thing about "absurd reality" humor is that, by doing it, you've essentially created an inside joke with the girl. Inside jokes are an awesome way to establish familiarity with another person, because now you have something that's just between the two of you - almost like a secret.
Don't go too heavily into any of the three staples. If you listen too much, then she'll feel like you don't have any personality. If you self-disclose with her too much, then the conversation may get too moody. You also run risk of falling into the "Friend Zone." If you use too much humor, then she won't feel very connected with you. Balance is very important.
I hope this helped.
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