Characters will make or break your story. The dullest story in the world can be enlivened by the proper use of characters. “I went to the store, I got caught in traffic, I saw a homeless guy on the corner, I had a fight with my girlfriend over the phone because I was late for dinner,” is a boring story in and of itself. Now let’s say that the homeless man you saw on the corner was actually a balding, bearded cross-dresser wearing Daisy Dukes, high heels, a crop top and a tiara and he’s actually trying to help by directing traffic.
Meanwhile your girlfriend is a transplant from Brooklyn who’s insanely jealous and she’s angry at you because she’s half-convinced that the reason you’re late is because you were busy flirting with women at the Whole Foods and she’s threatening to break up with you for the third time that week. And as she’s yelling at you, you’re too busy watching the crossdresser, who you have to admit actually has surprisingly nice legs.
Suddenly your story is much more interesting. The actual events are as nondescript as you can get, but it’s the characters who make the story work. You don’t have to have an amazing story full of excitement and adventure when the characters are unique. One of my favorite stories to tell is about the time I was at my favorite bar with my girlfriend when a dude walks in, hits on my girl, grouses at the bartender, hits on another girl at the bar and eventually leaves.
Except the guy? He’s a male escort clown1.
You don’t have to populate your stories with crazy, over the top characters. You just want to make your characters unique and vivid. How they look, what they did, who they resembled. Giving characters voices and mannerisms will add interest to your story and make it far more engaging and memorable. Just be careful not to go overboard; you want a caricature, not a comprehensive word-portrait.
Let’s face it: half of the time you’re telling stories, it’s because you want to brag about yourself a little. You want to let the woman you’re talking to know that you’re cool, that you do cool stuff, but you can’t just out and out say it. So you bring it up in stories.
The problem is, it is incredibly easy to sound like someone who’s trying far too hard… if you’re telling a story about your vacation to Vegas with your model girlfriend and you got upgraded to the VIP suite because you won $20,000 in a poker tournament, then the two of you ended up having dinner with Jeremy Piven at this incredibly expensive restaurant and then went and had bottle service at Rain, nobody is going to believe you. It may be God’s honest truth, but you will look as though all you were doing is trying to score cool points and impress everyone with how awesome you are. You think you’re looking cool. Everyone else thinks you’re a lying douchebag.
Instead, you want to leave out all of the cool bits; allude to them instead. Not only does this make the story much more relatable, but all of these unanswered questions bait women into asking about them. Suddenly you’re not bragging, you’re just answering her question. “So my girlfriend at the time just got done with a big project at work and we celebrated by going to Vegas. I had a great run at poker, so our room got upgraded. It was crazy. One of the guys, this high-roller at the table ended up taking us out to dinner, then we went and hung out at this club.” What was your girlfriend’s project? How much did you win? Who was the high roller? What club? All of these little unfilled details gnaw at the part of the mind that hates ambiguity and uncertainty.
Check in with your audience on occasion. These are little phrases you use to help keep people’s attention on you. “You know what I mean?” “You know what that’s like, right?” “No, seriously, check this out.” “Can you believe that?” These tags ask the person you’re talking to to become more involved and invites them to relate further to your story. It’s a very small thing that works wonders.
Use Sensory Language
The axiom that men are more logical and women are more emotional applies even with storytelling. One of the most common mistakes that guys make when telling stories is that they tell them…well, like guys. Guy stories tend to be very “Just the facts, ma’am.” The details they give are factual; it was 7:30 at night, it was an Audi A4, she was watching Sons of Anarchy on TiVo, it was two weeks before he broke up with his wife.
These don’t make for compelling stories for women. When you’re telling a story to a woman, you want to use more emotional and sensory language. You want to describe how you felt about things, how it smelled, what it tasted like, whether it was awkward or comfortable, warm or cold, exciting or dull. When you’re talking about a trip to an exotic tropical island, you want to create a sensual and emotional picture for them. You want to explain how warm it was and how you’d never seen water so blue and clear before. There were so few lights around that at night you could see the stars like they were diamonds laid out on velvet and you could smell the jasmine on the wind and how relaxing the sound of the tree frogs were.
Keep It Short
This is the last and most important point: brevity is the soul of wit and a long story is the death of the attention span. You don’t want to let your stories drag on. The longer you talk, the more likely it will be that you’re going to lose their interest. Keep your stories short and to the point; if your story is taking longer than a couple of minutes, it’s too long. You need to edit the fuck out of them and cut away the fat. If you need to, write them out in advance and just start trimming bits until you have something that works.
And don’t forget: practice counts for everything. Take time to tell your stories in the mirror. Learn how to find the proper pace of the story; not too fast, not too slow. Once you get into the rhythm and the structure of story telling, you’ll find that you’re the life of the party and that women will find you much more interesting.
- there’re pictures of him online too. I’m not linking to them. You’re welcome [↩]