A conversational tactic that gets good results for me is guessing / suggesting things about them.

"I bet you're a really good girl - straight As in school right?"

"Wow, I'm getting the feeling you're a lot more mischievous than people think you are"

"Oof, something in your eyes tells me you're no stranger to real life shit..."

They're flattered, curious what you see in them, and when you really nail it with a rare one, they feel completely naked in your eyes.

The less you speak, the better

There are two major phases of conversation I prepare for:

1) Challenge mode, where the conversation is like ping pong. In this phase she is probing you to assess your value and to know you better. Your goals are to provide a short answer to her question, perhaps a mild neg, quickly followed by some short stories to demonstrate value.

Example: Her: I'm currently a Chemistry major at Brown (University), how about you?

Me: Oh the schools that formed their own sports league because they couldn't compete with the Big Ten? You don't know what you are missing out. Several of my friends were in the (football) team while I was at Northwestern (University), we lived with a couple of our girlfriends in this house with 12 bedrooms and had parties every month.

My one of my close friends was Brad, I used to tutor him for Biochemistry. He wasn't the brightest dude, but man was he jacked. Once when we were waiting for the lift, he got bored and decided to run down 10 floors of stairs for fun. It was an old lift, but he was actually faster than the lift!

Her: Cool, do you still live with Brad?

Me: Oh Brad moved back to his (small) hometown a couple of years back, he's now a bricklayer at XXX construction company. I moved on to Boston to join XXX company as an analyst for a couple of years before working on my MBA at Stanford. I still keep in touch with him... (pause and look wistfully into the distance and sigh with a small smile), those were the days, we were much poorer, but everyday was fun. Did you have any similar experiences?

(I have 2-3 stories I can tell for generic questions/situations)

Me: Another of my housemates was this dude we nicknamed "Druglord". He and his then girlfriends were permanently stoned and once when the cops showed up at our front door... (cue 2-3 crazy incidents). Can you believe that he is now a reputable dentist at XXX clinic? If you ever need any dental work done, I'll be happy to recommend him to you, he has an extensive experience with anesthesia... (smile)

Her: (Laughs nervously)

2) Story mode. Usually reserved for more introverted girls. I have a bunch of stories I can tell to keep the conversation going.

Example: Her: (quiet as prior conversation topic ended)

Me: So what was the most exciting place you have been recently?

Her: Mexico City, I spent a week there with my family, last summer.

Me: Cool! Last summer, I spent a month in Patagonia where I trekked around the tip of South America from Buenos Aires to Santiago with a couple of friends... (a) describe the good scenery, (b) there was only 1 toilet in the hotel room and the girls took an hour to get ready every morning, (c) how I had to shove a beggar away from my friend when she was harassed in a coffee shop, (d) Fine dining experiences, e.g. how the Steaks were better in Argentina, while the Chilean Seabass was amazing, (e) Visits to interesting locations like a vineyard for wine tasting. etc.

I can monologue for at least 15mins for just this single trip/topic and I have several other trips to talk about. Other general topics I prepare for include, 2-3 sports I am interested in, technical STEM topics and fun facts, some popular TV shows/movies, financial planning etc.

Caveat emptor: I am not a natural conversationist and I rely on these tactics to keep conversations going. If someone where to speak with me for perhaps a total of 6 - 10 hours, I would eventually run out of 'exciting stories'. I have also received feedback from those close to me that I can come across as an "arrogant person". Women that I had rejected previously had commented to their friends that "They were not my match".

Basically what's helped me not even have to worry about it anymore is: Whatever she says > you comment on that. It doesn't matter what you say either.

Take any random fact she tells you about herself and tease her about it.

Tells you she does x - you go: oh no way, you're that type of girl? Alright well I just remembered that I had to meet with someone right now, it was really nice to meet you. I promise its not you, its me. All with a shit eating grin on your face

Tell stories. Best stories?

Stories about other girls and sex.

Always steer the conversation towards *spicy topics (relationships, etc.).

Easy to set thw right frame and implant whatever you want in her mind. Escalate from there.

Ok..... conversational skills I've learned.

Basic

Talk clearly and fairly slowly.

TALK LOUDLY ENOUGH.

Keep every sentence simple. Build to more complicated stories and scenarios with simple sentences. Each sentence should say one thing only. This really helps when talking to strangers. Strangers cannot comprehend complicated sentences at the same time as trying to understand your accent plus intentions plus non-verbals, so keep it simple and take your time.

Story Telling

Practice story telling... if something happens to you and you want to retell it, make it into a little story. Every story has the same structure:

• Some sort of bait / introduction / appetiser. Enough to motivate the listener. "Hey, did I ever tell you guys about the time I was arrested?"

• Set the scene and provide context. "So you know when you're just walking down the street and in your own little bubble..... well it was a day just like that" or "Ok, so I'm out in a bar with Jim, James, Jimbo and Jimbob, they're all really great guys but the kind of guys that will always end the night in trouble".

• The bulk of the story, interesting events. Make sure to convey as much emotion and intrigue as possible. Make sure the audience knows the main characters, describe the events. 99% of the time you want to cover the story in chronological order. If people interrupt or ask questions you can answer them and weave their interests and comments into the narrative. If you can refer your story to anything they've said that really helps with their interest..... "right, and just like you were saying earlier about that bent cop, this guy was also....."

• Make sure it has a god damned interesting conclusion. Not exactly a punchline, but a satisfying conclusion, some way to wrap it up. This should be fairly positive... "and that's how I got away with it" or "and that's how I learned not to shoplift" and not "I have never recovered and my life is now a ball of sadness and despair". This is the point where you can break the chronological order if it helps to wrap things up nicely if there isn't an otherwise natural end.... "yeah, and right in the middle of it all, it turns out that my friend Jimbob is actually a transexual, which puts a whole different colour on the events of that night".

You can then optionally lead into another story ... "And so yeah, that was the first time I was arrested", but you need to make sure you are not falling into "dancing monkey" mode where you are their entertainer. The basic sketch here is that you are in control of the conversation, not them. Get them to talk at this point... listen to their sucky stories (and be positive about them), lead the conversation, don't be led.

DON'T ASK QUESTIONS

You don't want to ask questions. You want to talk in statements. "What do you do" / "Where are you from" is the fucking worst........ interview style question and answer is fucking awkward as hell.

At the very least if you want information you should phrase it as an order...... "Tell me what you do". With guys you can just ask questions, it's fine..... but with women it's best to make them feel compelled to answer you in some way...... "I bet you're a hairdresser".

People love talking about themselves. It works on both men and women. Let them do all the work.

Good topic, I'm curious to know other people's tricks. One thing that I recently started doing is asking the girl her worst experience instead of her best : "What's the worst place you've been to?" "What was your worst date like?" "Who do you hate the most?"

Sometimes the conversations I was having with some girls were too positive and it just comes across as bland at one point, it's a good way to add a little twist and shift emotions. And women love bitching about their life.

Reposted from main site:

Something I like to do is ask fucking weird, retarded shit that people don't expect.

• "Who's the tallest man you've ever seen?"
• "Have you ever eaten citrus ice cream?"
• "What’s the most ridiculous fact you know?"
• "What's the weirdest thing you've ever smelled?"
• "Do you believe in the power of a curse?"
• "If you were a teacher, what would you teach?"
• "Would you spend the night in a cemetery?"
• "What's the most overrated place you've ever been?"

Works on men and women. Always gets a laugh, and they will always answer.

And they're formulated in such a way that it gets them to open up about a memory, experience or their likes/dislikes.

The more ridiculous and outlandish the question, the better.

My go to question for breaking an awkward silence is:

"So... what's your opinion on the price of butter these days? It's absolutely criminal".