The No-Risk Method to Dating Mastery
We all know that practice makes perfect. And like anything else, working on your romantic skills will help you attract more people and build stronger connections.
The tricky part, though, is that practicing this stuff comes with high stakes.
When you’re learning something like piano, messing up is no big deal. You sound terrible for a second, get frustrated, and then try that chord again. But if you go talk to someone and make a fool of yourself, you have to deal with the potential face-to-face awkwardness and rejection.
And that’s why some guys read a TON of dating advice while not putting any of it into practice. They’re trying to hone their skills from a safe distance without having to endure any real-world pain.
Of course, they soon realize that all the reading in the world doesn’t replace genuine knowledge gained from experiences. They decide to avoid all social risk-taking and stay stuck in boring, platonic interactions or settle for no interactions at all.
Then, they accept that they just don’t have what it takes.
I hate to break it to you, but it’s impossible to improve your dating skills without trying new things that expand your comfort zone. That’s the only way to get better.
But what if I told you there was a way to practice AND minimize the odds of getting hurt?
Sports athletes don’t just get experience while in the game, they practice off the field all the time. You can do the same, too.
You just need to find avenues where you feel more safe or less invested in the outcome to take action. That will give you the foundation and confidence to practice in more challenging situations and then get better results, too.
Let me give you some examples. So let’s say you want to start…
Asking better questions in conversation
Stale questions encourage people to give you canned, unenthusiastic responses. That leaves you with little to no interesting content to continue building an engaging conversation.
This is especially true when you only stick to logical questions or questions you don’t care about. Do you think asking how long she’s been a copywriter will excite her? Do you care if she actually comes here often? Probably not.
You can improve your questions by adding in one or more of these elements:
Keep them open-ended. Yes or no questions close the door.
Get to the emotions behind the subject. This doesn’t mean you have to get sappy or deep — you can stick to empowering emotions like joy, curiosity, and passion. Instead of asking a girl for pure data, ask how does something make her feel? What is her motivation? Why does she like that subject? Why is she so passionate about it?
Ask something creative they haven’t heard before. This gets people to actually think about their response and be more vulnerable with you.
The problem is that many guys feel like they don’t have the wit in the moment to follow these rules. They can’t think of better ideas so they just ask the same terrible questions people have heard repeatedly. Instead:
- Google something like, “interesting questions to ask people” and start gathering ideas. Just seeing all sorts of different questions (especially ones that are more unique) will help you start coming up with your own engaging ideas.
- Every time you meet someone new, jot down specific ideas you learned about them after the conversation. For example, “studied creative writing, from Wisconsin, works as an editor for a publishing house.” Then take each of those ideas and brainstorm anything you could ever want to know about them.
- When writing down question ideas, force yourself to only create questions that follow the above rules of being open-ended, creative, and evocative. This exercise will make it easier to produce these types of questions on-the-fly.
- Create an anonymous Quora / Ask MetaFilter account or join a hobby forum and start asking these thought-provoking questions. Get a feel for which questions inspire people to respond enthusiastically. Ask follow up questions that further push people to reveal more about themselves.
Developing your wit to improve texting and online messaging
Long, overly serious messages when you’re first talking to a woman is a death sentence. She’s not emotionally invested in you at that point. If it becomes a chore to respond to you, she’s more likely to walk away.
A woman should laugh or smile when she sees your messages. You might already understand that, but feel like you don’t know how to be funny. You think you don’t know how to make a woman laugh so you don’t even try.
It starts by understanding that you need to re-frame your mindset. Stop trying so hard to make women laugh and focus on making YOURSELF laugh.
Because what’s often funny is you not taking yourself so seriously and expressing your sense of humor. A girl doesn’t need to have the exact same sense of humor as you to appreciate your silly side. You don’t have to be over the top if that’s not you — embrace your dry or sarcastic style of comedy instead.
Also, brevity is the soul of wit. The best messages are usually short, around 1-2 sentences. This works in your favor because you don’t need to practice writing long, thorough paragraphs or invest a lot of time. You can do small brainstorming sessions which also help cultivate the right mindset for messaging.
- Join an improv class. Improv is literally the art of building your wit and creating content in the moment. Everyone I know who’s taken improv has made a huge shift in the way they communicate even after only a few sessions.
- Write your messages using The Up-Goer Five Text Editor. This is a tool inspired by an XKCD comic which limits you to only using the 1000 most common words in the English language. Therefore, you have to learn to express more emotion or bigger ideas while writing clean and simple.
- Draft your messages on Twitter so it forces you to stick to 140 characters or less.
Pick an idea that strikes you from a girl’s profile or message to you. Maybe it’s Home Alone being her favorite movie. Open up a Google doc and set a phone timer for 1 minute. Try to immediately jot down every word or idea that comes to mind from Home Alone. Examples: Kevin!!!!, iron to the face, Joe Pesci eating fingers, what happened to Macaulay Culkin, if only he had a cell phone.
It doesn’t matter if some of the ideas are stupid — that’s the point. From there, take one idea and try to flesh out a single sentence or two on it. “I still have nightmares of Joe Pesci eating my fingers — horrifying.” or “If Kevin had a cellphone, that movie would have been over in 30 seconds.”
- Set a timer to send/reply to a message in 1 minute. Guys spend too much time racking their brains for the “perfect” message when they just need to write a half-decent lighthearted one. Time constraints often help us go with our gut and not overthink. If you can’t message in that time frame, move on to someone else, and come back to it later.
Getting better at flirting and being sexual
Flirting is any action that demonstrates romantic interest. And that means there are lots of ways to flirt in conversation. You can utilize compliments, teases, innuendos, and more intimate questions.
Maybe you struggle to flirt like this during dates or over text. You’re worried that you’ll slip up and say something stupid. So instead you just play it safe and hope something just happens. This doesn’t work because…
Flirting is usually what starts arousing a woman who’s engaged by you. That’s when she sees you as a potential sexual partner and flirts back. It also helps set the mood before a date so you both go into it knowing what to expect.
I’ve witnessed too many guys talk to women who are interested, only to have them lose that interest when the connection doesn’t escalate. To practice, you can:
- Use a random chat service like Omegle or Chatib to practice being bold with people who don’t know who you are. Note: You may have to go through a couple bots to get someone real.
- Swipe right (yes) to girls on Tinder you’re not fully attracted to. Then once you start chatting, try being more sexual with them using the articles linked above. Since you’re not worried about meeting up, you don’t have to worry about losing them. Note: Don’t get stuck on this forever and just use girls for practice or validation.
- After a date, write down what you found interesting about that girl. Then write sincere, succinct compliments based on those ideas following the advice here.
- Tell a girl in passing in public what you like about her and then walk away. That way there’s no chance of rejection. You can just get the reference experience of having people perk up and thank you which will encourage you to start showing more interest to women.
- Once you’ve become comfortable with creating genuine compliments on paper or saying them in passing, give one of those compliments on your next date.
Getting comfortable in new social situations and introducing yourself to strangers
Going to social events, especially by yourself, can be mentally challenging. The unfamiliarity of what to expect terrifies a lot of men. They don’t want to sit alone and be judged as that “weird guy”.
Then it becomes even more stressful when those guys start thinking about having to talk to girls. They always tell me they have no idea what they should say. They’ve never done something like that before and therefore feel like it’s impossible to start a good conversation.
All this anxiety stops them from even getting out of the house. They see it as black-and-white: if they’re not going to chat up a lot of women, they shouldn’t even bother going to those venues.
But you don’t have to start cold approaching every beautiful woman you see. You can:
- Practice talking to people who don’t intimidate you or can’t reject you. Talk to lots of guys. Approach cashiers, bartenders, and working people who are paid to be polite. Make situational comments to older women or women you aren’t into. Build that social muscle and get used to handling conversations with all sorts of people — it’ll make talking to attractive women.
- Go to an event or class and do nothing. Just show up and get comfortable being the guy chilling alone. Take the pressure off approaching anyone and just try to enjoy yourself. Even set a 30-minute time limit and then leave. You can increase your future staying times and eventually work up to talking to people.
- Only go out with the intention of making friends. That includes attractive women. I want to remind people of the intentional “friend zoning” exercise I often write about. Take any kind of objective for attracting someone off the table.
Make observations and write down things you could say to people. What’s going on around you? What do you notice about them? What do you find interesting / funny in the environment or about that specific person?
For example, you see a girl sitting by a tree in the park overlooking the water. You could say, “It looks like you found the best spot in the whole place.” The best openers don’t have to be super clever, just relevant. Or you see a girl in a museum looking at a creepy painting of an old woman, “That’s like the scariest postcard you could get from grandma.” You can see more examples to use in any situation here.
- Try one of the 18 exercises here that work your way up to approaching new women.
Becoming a better storyteller. A great story is a powerful way to engage people. Even just 30 seconds of sharing an experience can hook people in and have them intently listening to you. But that’s only possible if you’re sharing actual feelings and details about your life rather than just, “Spain was beautiful.”
What prevents people from sharing stories is the fear that their stories won’t be cool enough. They think that something epic or badass had to have happened to make it worth telling.
A good story can be about many things: your unique observations or take on the experience, what you personally learned from it, what it meant to you, or even something silly or mildly amusing that happened.
To uncover those ideas, you really need to think about your experiences and relive them.
- Take a creative writing class that forces you to understand narrative structure and how to craft compelling stories.
- Join Toastmasters or a storytelling event where you can practice in front a safe, live audience and get feedback.
- Start submitting short stories to a public forum like Reddit’s Short Stories community. You can get real critiques while remaining anonymous.
- Now think about any memorable experiences you’ve had over the last couple years: during travel, at an event, with friends, or even on dates. Create a document fleshing out an interesting/insightful/funny stories from them. Once you’re aware of them, you can have a couple of “go-to” stories for meeting new people and eventually wean yourself off them.
You can’t just digest knowledge and expect to grow. But you also don’t have to immediately try with women you desire if it’s too overwhelming.
You just need some kind of output — even if that’s practicing by yourself or through situations that act as a stepping stone. You’ll be constantly improving and soon you can start trying those new abilities in the romantic situations that matter.
Patience and creative practice will lead to dating mastery.
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