(This is a follow-up article to my post Turn Rejection Into Success, Part One.)

“Throughout our courtship, Kenny told me that he had proof that Saddam Hussein was a threat because he possessed weapons of mass destruction. I told him, 'You had me at weapons.'” – Renee Zellweger

Asking people out is easy. In fact, it’s the easiest part of the entire relationship process. By definition, it has to be the first step, yet many people never make it that far, simply because of the fear of rejection.

Here’s the secret: repetition.

Not asking people out because you might be turned down is entirely self-defeating. It’s like not applying for a job because you might not get it or refusing to cross a road because you might be hit by a bus. Your mentality is backward from the start. Subsequently, this negative attitude increases the chance of failure, which will then decrease the number of times you will be prepared to try.

I’ll be honest with you – a lot of the time, you will be turned down. Understanding and accepting that this is the inevitable start of your journey towards true relationship enlightenment.

1. Ask people out. Often, and I mean, a lot. Not the same person – that’s the fast route to crazy and/or jail – but many different people. Make a habit of it. When you’re out at a club and see somebody you like, ask them out. What’s the worse thing that can happen – they can say “no,” right? So what? What difference does that really make in the grander scheme of things? So you’re a little embarrassed or hurt. You’ll get over it. You may never get over not asking. Like applying for jobs, or playing the lottery, the hit rate on relationship application success is low. If you let one rejection set you back to the point where you stop asking, you’ll never meet anyone.

2. Use your common sense. Aim high, but don’t try for the majors if your batting average stinks. Practice, practice, practice. Then work your way up to the majors. The idea that somebody is “way out of your league” is generally put into our heads by people who feel that way about themselves. How many times have you seen a great-looking woman with a so-so man, or vice versa? How did that happen? They asked. Beautiful people (certainly women) often complain that nobody asks them out because they fear being rejected. Could you hope for any more of an invite?

3. Don’t ask people out in front of a crowd. Do make sure they can hear you properly. If that person gets weird or mocks you about it, count your blessings that they said “no” and move on.

4. Keep on asking. Roll with the punches. Ask, ask, ask and then ask some more. Over time, those stings will become less significant. More importantly, the actual process of asking will no longer be any kind of hurdle.

5. Practice makes perfect. Go to a mall or the beach. See somebody you like and ask them out. Whether they say yes or no is immaterial; the point is you’re conditioning yourself to ask people out. The more this happens, the more accomplished you’ll become. This is particularly true if you’re rejected a lot. It doesn’t matter. Keep your spirits up, stay positive, see the humor in it all and keep asking.

I’m not telling you to become a stalker. I’m telling you to become a pro. Do anything enough, and it becomes second nature. It becomes natural and ceases to be awkward or difficult. You’ll get good at it. This, of course, breeds confidence, which will make you better at it.

Condition yourself to reject rejection, and never look back. Easier said than done, you say? Not so – I’ve been there.

At best, I’m an average-looking guy. Despite this, I have an enormous amount of self-confidence and a quick wit. This served me well during the latter years of my education, when I used this winning combination to date one of the best-looking girls in the entire school for two years.

And then she cheated on me.

Looking back, it was “soft cheating”- cheating with an asterisk. She went on a trip, got drunk and kissed some guy. She confessed and was completely broken up by it. First, I shrugged it off, but it began to consume me. It was less about the “what” and more about the “why.” Why had she done this? Clearly, something was wrong with our relationship, otherwise she wouldn’t have acted that way, drunk or not.

We split up. It was a messy break, which involved several big heart-to-hearts every few weeks for a couple months. She still loved me. I was done. In my own warped way, I had become the rejecter, but so had she. Moreover, she planted a seed inside of me that would grow into something pretty ugly.

Five years later, I was smitten with another girl. We dated for about a year, and then decided to buy an apartment. I should have realized things weren’t working out when, literally an hour after signing the deed, she told me, quite explicitly, she wasn’t sure we should be doing this. Within six months, we split up. I came home one day to find her stuff packed a note saying she was gone and that she’d met someone else.

That was two strikes against women.

I eventually moved on and started to pursue somebody else. Pursue is the right word, as for a while I dangerously flittered between lust and obsession. The girl of my adulation fluctuated between very interested and very aloof, which both confused and excited me.

After a couple months of mixed messages, she said it wasn’t going to happen. This was a good thing. I was entirely caught up in getting her to say “yes”- the thrill of the chase. She was like an eBay auction. You see something you like and you’re determined to win with bid after bid after bid. It’s all you can think about. You end up paying way above your comfort level. A week later, when the package arrives, you realize you didn’t really want it after all.

At the time, all I could see was “fail.”

Three strikes and you’re out.

Naturally, this hardened me. I became the master of my emotions. Envy, jealousy, desire, lust? These were the weaknesses of mortal men. I no longer felt these things. I laughed in the face of rejection – how could I possibly be rejected, when I simply didn’t care?

It took a decade to work my way back to back to something just a little healthier, finding the balance between self-control and empathy. I’m not quite there yet, but I’m close.

I’ve been married to a wonderful woman for nearly 12 years. With the security of an adult relationship comes the wisdom in recognizing the folly of one’s youth. I did many dumb things. What would be dumber still is not learning from them. If I had let the fear of potential rejection keep me from persevering, I wouldn’t be with my wife today. She was definitely worth the risk.