9 Ways To Pump Up Your Conversations

By Lance on May 29, 2008 in Dating, Featured
Okay dudes, I’ve been thinking a lot lately about the difference between good dates and bad dates. A lot of it comes down to having good conversational skills…all the advice out there says that exchanging information and interviewing each other is LAME, which is correct. “What’s your job? Where are you from? What’s your favorite color? What color are you panties?” Next! You want to find ways to connect with a person on a deeper level.
I’m a pretty kickass conversationalist–yeah, I said it–so I sat down and analyzed what I did. It boils down to being able to articulate well, developing multiple threads, and having great content (it’s kind of like blogging actually). I’m assuming you’re a good speaker and can maintain multiple threads, so what I want to do is analyze the content side of the equation. In my mind, having good content the key to excellent conversation. Basically, you want to have material that gets both parties engaged.
Here are 9 ways to pump up the content of your conversations:
1. Tell Personal Stories – This is the core of my conversational repertoire. I tell stories early and often, and over the course of a good date, I’ll probably tell upwards of 8 stories. Most of them are humorous and all of them reveal something about me. My goal is to paint a vivid picture of who I am, what I value, and what kind of life I lead. I divide my stories into three categories: high value, takedowns, and random-funny.
What do I mean by high value? A good example would be a story about surfing in Australia. Everyone values traveling, so I’ll describe traveling adventures and really paint a picture. I’m pretty slick about not coming across as self-promoting, and what I usually do is inject humor into all of my stories. The last thing I want is to come across as a douchebag.
Takedowns are stories that take away value from me. I do this on purpose to keep me grounded and accessible (because I am grounded and accessible). This is a super important point…you must mix in takedowns! Why? Because otherwise you’ll come off as snobby, arrogant, conceited, narcissistic, douchebaggish, and a whole host of other unattractive qualities. If you come off as too high value, the girl might even think she’s overmatched or has nothing in common, which happens in an older guy/younger girl arrangement.
A takedown would my most embarrassing moment. Another would be the time I got suspended from high school for fighting. A lot of the stories can be both high AND low, which is great. For instance, if I told a story about getting busted passing love notes in my Honors History class, that’s both high value and a takedown. Calibrate to the girl and make adjustments on the fly.
Random-funny stories are usually dumb little funny things that happen on my daily travels. These are more like anecdotes and don’t do much to your value. An example would be if I described to my date how I got stung by a bee while mowing the lawn. I use to these to flex my sense of humor.
It’s important to note that I don’t dominate conversation and string together 10 stories in row. I’ll tell one and wait for her to tell one back, or switch threads. The point is, you want to have access to a large arsenal of personal stories and use them when appropriate.
2. Travel – Travel is a goldmine of conversational content. Not only does it provide source material, but it says you have the means and the interest to travel, plus it gives you perspective because you’ve interacted with people from other cultures. The subject of travel is worth a whole post, but suffice it to say if you haven’t done any, you’re at a disadvantage. Go on a big trip. Better yet, go backpacking around Europe for the summer. Then share your stories and insights.
Hey, international travel is expensive. I feel you. If you can’t afford to go overseas, my solution here is to go on road trips with friends. Some of my best stories are about the roadtrips I did in college.
3. Read Magazines – This always gives me material to talk about. If you don’t want to subscribe to magazines, go to Borders and read 5-6 mags per month. Try a diverse range. And no, I’m not talking about ESPN The Magazine. Read stuff where you know the content will crossover well to a female audience. Here’s what I read: GQ, Esquire, Time, Harper’s, Scientific American, Fast Company, National Geopraphic. Sometimes I’ll read a few more, sometimes less. I always get good tidbits that I can inject into conversations
Here’s a sampling of topics this month from those mags:
Secrets of Stonehenge.
Super colorful sea slugs.
The reason behind chronic itching.
T. Boone Pickens: $10 Billion wind farmer.
Lakshmi Mittal: Richest man in Britain.
On the campaign trail with Obama.
History of gay marriage.
Chinese government getting props for dealing with earthquake.
Arnel Pineda: New lead singer of Journey. From Manila!
Are you kidding me? There’s a TON of cool shit right there.

(Chicks dig super colorful sea slugs)
4. Cool Internet Sites – Try media heavy, information packed sites like Gawker, Boing Boing, and Huffington Post. Special points if you read The Onion. I hesitate to mention Internet stuff because it’s too easy to geek out on the ‘net, so be careful. If you’re on a date, don’t freakin’ talk about your Facebook friends or I’ll pimpslap you. Weave in news, trends, errata, and random fun stuff. The important thing to remember is voice your opinion and don’t simply regurgitate information.
My latest is talking about music sites such as pandora.com and playlist.com. From there I might talk about iTunes, downloaded music, or transition to a great concert I’ve been to. Then, after you’ve got her pumped up about the sites, take her to your house and demonstrate how they work. Then play some tonsil hockey on the couch.
Oh yeah, I’d be a douche if I didn’t plug honeyandlance.com…mention it to your dates and tell them what a fucking cool website it is!
5. Read Books – You know what I like to do? I go to Borders and read chapters in a wide array of non-fiction books to increase my knowledge base. I’ll read business stuff, personal finance, personal development, biography, history, astrology, sex books, whatever. I sometimes read fiction in the store, but I try to buy the novels and take them home. See, the point here is to be able to weave the knowledge into the conversation, and not just SAY that you’ve read a certain book. A good example would be if you have a date with a finance chick, you can hang in a finance conversation because you’ve read books about personal finance, investing, Donald Trump, and Robert Kiyosaki. Again, have opinions.
If you get a chick who’s really well read, you’re pretty much screwed if you don’t read at all. She’ll select you right out. I’ve talked to tons of chicks who’ve expressed exactly that. Keep a close eye on this detail if you’re an online dater because it’s a dealbreaker.
Also, go read sex books and learn as much as you can on the subject. Men who know how to please woman are super attractive. That in itself will get you laid. If you actually know how to stimulate the g-spot and she knows you know, that’s big points for you.
6. Watch Gray’s, House, Lost, etc – This one is painful for me because I don’t watch non-sports television, but it can be very useful. If you don’t watch TV either, try to pick one popular show per week. Every chick watches Gray’s Anatomy. Watch Gray’s and talk about the relationships with your date. What character do you identify with most? Form an opinion. I love Lost, and when I find a chick that digs Lost as much as I do, I’m going to marry her.
Psyche!! Seriously though, I can talk about Lost until I’m blue in the face. That’s my one show.
Also, I happen to have a crush on Sex and the City and this has been a great convo tool for me. I’ve even developed it into a little routine where I ask what character my date identifies with most. From there you can transition to talking about relationships and sex.
7. Bar Games – On dates I like to play what I call “bar games.” In pickup parlance these are considered routines, but whatever. I think of them as tools to stimulate conversation. By playing a bar game, you’re basically generating content on the fly. The simplest bar game is to people-watch and try to guess what they are talking about, or guess what kind of relationship a couple might have.
TIP: This is a slick way to introduce the theme of sex on a first date!!
Okay, example. Let’s say you see a older guy/younger woman couple across the bar. You ask your date to guess what their relationship is like. She takes a guess. Then you say:
“I think they’re on their 3rd date and she’s a crazy golddigger and he bought her a car. Not a Toyota either, but a BMW convertible, cherry red. The thing is, she’s the kind of girl that would give the guy head in the car on the way back home and then DUMP the guy for another rich dude.”
Use your imagination, lead the interaction, and sex it up. Games like this make it easy to transition to a sexual frame. From there, you’re practically off to the races.
What else is this good for? Talking about relationships illicits values. Is she a prude or wild? What does she consider attractive? Is she okay with an older guy/younger girl arrangement? This is knowledge you want.
8. Marry, Date, Dump – This is another routine that I do on practically all my dates. It’s a blast. You pick out three dudes and the girl has to say which guys she would marry, date, or dump. She can’t use the same category twice. Her answers are based 100% on looks, presentation, and body language (which is actually a lot of information). Then she has to explain why she chose who she chose. Then, it’s her turn to pick three women for you. You would be surprised at what an amazing amount of information you get from these cold readings. Again, this tells you about your date’s values and perceptions of people. This game is not only fun for me, but it adds to my social knowledge base.
As with #7, don’t just play the game, use it as a tool to talk about social dynamics, because that’s where the real communication is.
9. Ask Great Questions – Well, I would be completely stupid if I left this off, but duh here it is. Obviously, asking questions and responding and adding your two cents is a huge part of having good convo. Don’t just ask questions though, ask great questions. Ask those questions that are wide open and require the other person to think deeply.
Here are some great ones I’ve asked on dates before:
“If you could live anywhere in the world, where would it be?”
“What are you really really passionate about?”
“If you won the lottery, what would you do?”
“When you were in 4th grade, what did you want to be when you grew up?”
“Would you give your phone number to someone you just met in bar?”
“What’s the worst date you’ve ever had?”
“Would you sleep with someone on a first date?” (I always get great reactions to this one.)
“Where’s the craziest place you’ve had sex?” (use to transition to sexual frame)
Okay, there it is, nine ways to pump up the content in your conversations and have better dates. Any others? Leave in comments below.