By · @the_popular_man  ·  · 53 Shares

I’ve talked about boldness in articles before. Dating has always favored the bold and those willing to take risks. However, in 2016, with dating as competitive as ever, boldness and risk taking become even more essential to find success.

I’ve met countless people who are unhappy in life, often due to lack of meaningful relationships. It’s amazing to me how many people get into ruts and refuse to take the steps necessary to be happy. Ruts are very comfortable. But, the tradeoff is that staying in a rut usually doesn’t lead to happiness.

In most cases, finding that special someone requires you to break out of your rut and take a few risks. I’ve listed three below. While they might make you very uncomfortable, especially at first, you also might find that they can change your life if you apply them consistently.

Just Say It

Date and Dating Tips in Being SuccessfulWhen I was in high school, I was given a detention under a very dubious circumstance. I wanted to plead my case and explain why I didn’t deserve a detention. It might not have worked, but at least I could’ve gone to bed knowing I spoke my mind. Instead I stayed silent before the teacher, whom I still think was in the wrong.

Now, I always make an effort to speak what’s on my mind. In fact, I’m known for being pretty bold and assertive about what I want. Not only do I feel better about myself, I often get what I want by being assertive.

For many people, especially shyer ones, actually speaking up and saying what’s on your mind might be a huge risk. But, if you want to get what you want, in life or otherwise, you have to speak up.

While you don’t want to be too much of an open book (keep some mystery), in dating and relationships, boldness always helps. I know many people, clients and friends, who live with long term regrets related to their lack of boldness with others.

Usually, they lacked the courage to either start a relationship or take it to the next level. In some cases, this lack of courage has left them wondering “what if” for many years down the line, especially if they feel like they lost out on an amazing relationship with a special person.

While you don’t want to be creepy or abrasive, being more open and bold with others, especially those you find attractive, should help you not only get dates, but also achieve what you want in those dates. And, especially for men, boldness is considered very attractive.

Talk to Strangers

When I was younger, I remember hearing “don’t talk to strangers” a lot. Of course, it’s a good message for children since the strange person at the playground could be a kindly old gentleman who is there with his grandson or a kidnapper wanting to do horrible things.

But, as an adult, the best advice for dating is: “talk to strangers.” In fact, unless you have an unusually large social circle, if you don’t talk to strangers you’re likely going to be single for a long period of time.

When you’re growing up at school and even into university, you’re around a lot of people who are of similar ages and interests. Dating might not be easy, but you typically have a large enough social circle that it’s easy to luck into a few dates at least.

But, as an adult it’s not so easy. Usually your circle of friends has considerably narrowed and places where you spend most of your time (like a job) aren’t always conducive to dating. So, meeting a partner becomes considerably more difficult.

Date and Dating Tips in Being SuccessfulIf you want to meet the man or woman of your dreams, unless you are getting randomly hit on all the time or fixed up by family and friends, you’ll have to shed the childhood advice and talk to strangers.

Talking to strangers is an anxiety inducing task for many people. Not only do you face a good chance of rejection approaching random people, you might even look awkward and ridiculous if you don’t do it right.

However, done correctly, which includes being funny, charming, and definitely not creepy, you have a good chance of succeeding. While you might not get a relationship, or even a number, you can at least make someone’s day better.

If you take this risk often and do it well, I promise you won’t be single long. And, you’ll likely have made many friends in the process.

Reinvent Yourself

A good friend of mine from high school had been grossly obese his whole life. He was known as the “fat kid” and had been largely dateless throughout high school. After graduation, I didn’t see him for a couple years until he knocked on my door. I didn’t recognize him! He had lost over 150 pounds.

He successfully shed a bunch of weight, took up fitness activities, and reinvented himself. He not only started to create a better life for himself, but his newfound confidence allowed him to get into multiple relationships over the years since he kept it off successfully.

While speaking your mind and talking to strangers can be very difficult for shy individuals, the biggest dating risk is to reinvent yourself to become more attractive.

While not everyone is in need of this, there are some people who, for whatever reason, are so unsuccessful in dating and relationships that the only solution is a full reboot of their look and personality.

However, most of us have at least a few things we could improve on, whether it’s being less needy, losing weight, updating a wardrobe from 2006, or any number of things.

Change, even good change, can sometimes be extremely difficult. That’s why it might be the biggest risk of all. Modifying long term habits, mental states, and even spending large sums of money to improve are all bold moves. Sure, they might pay off. But, they also might not. That’s why it’s a risk.

But, if the change makes you more attractive, then it will definitely result in you getting more dates. If you’ve been single and miserable for a long time, then a big change or total reinvention might be in order.

Some people might argue that this change will make you lose your “core personality.” I’m not asking anyone to do that. However, if there’s a part of you that’s keeping you lonely and unhappy, then my opinion is that it needs fixed.

I don’t believe “being unhappy” is a core trait for anyone, especially when it comes to love and relationships. If you’re constantly unhappy, then it’s definitely time for a change, even if it means pursuing difficult and long term change.

So, if you’re constantly single, then these three risks should help you get that much closer to a date. Yes, they are risks and might not work out. But, the reward (a happy relationship) could be amazing.

Jonathan Bennett

Jonathan is an author, relationship expert, and counselor. He owns a consulting business that helps men gain confidence and attract the woman of their dreams.

Author, consultant, and relationship expert, he runs The Popular Man and Love Advantage

What Do You Think?

1 Comment | Join the discussion

  • Onyeka Ineh May 13, 2016 at 11:54 am

    Thank you Jonathan, I read through your article it’s a great advice. I love what you guys are doing and I enjoyed every aspect of them all. Thanks again and God bless you.


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