Creating Challenge in a Relationship: A True Story About a Girl and 3 Guys

Creating Challenge in a Relationship: A True Story About a Girl and 3 Guys

Hello. Gregg here with another reader story about a guy- or in this case – 3 guys. This story comes from Amber, who agreed to let me share her story. She will tell you why you should be creating challenge in your relationships!

I had my first boyfriend in 8th grade. We held hands on the bus, and broke up right before the big Middle School Dance. I dated guys here and there throughout high school, but nothing serious. Football players, skateboarders, musicians — the usual stereotypical high school guys. Then, in my junior year, I met a guy through the drama club. He had the lead in the school play and all the girls were in love with him. He was a total Momma’s Boy. So much so that after we finally broke up, his mom called me and said (yelled) some pretty awful things — to me. This was despite the fact that I found out her son had cheated on me not once, but twice, and followed an incident where we had a big argument in his Trans Am – when I finally told him it was over, he left me on the side of the road and drove off! Talk about drama. The relationship lasted 6 months.

My next boyfriend was the Cool Guy. I had a crush on him since 9th grade and then, senior year of high school, we finally started dating. He played guitar in a grunge band and was the typical moody artist. Total narcissist. He always put himself first — and his friends. I came in third. But he was just so cool. I knew if I broke it off, some other girl would be waiting to pounce on him. We dated for a year and carried over into freshman year of college, until one time, I came home to visit him and he already had plans with his buddies. That was the end of that. I finally lifted that cloud from my eyes and dumped him, then spent the weekend venting to my girlfriends.

Fast forward to sophomore year in college. I went on some dates but never really found a guy that kept my interest. Until I met him – It was love at first sight — for real. After some chance meetings, small talk, and wistful glances across the room on both our parts, he asked me out. We went to the movies and then for coffee. We were so in love, we talked about getting married on our first date! It was a whirlwind after that. We were together 24-7 and life revolved around our relationship. You can guess what happened next. After about 6-months, he decided he needed a break — from me. His schoolwork was suffering and (since he got a great girl like me) he wanted to see what else was out there. Seriously. I gave him an ego boost. Just like Gregg warns us in To Date a Man, You Must Understand A Man, I wasn’t a challenge.

Now, here’s where it get’s good. Instead of crying and feeling sorry for myself, I hung up the phone with him, and invited some girlfriends over for a sleepover party. We drank wine and watched rom-coms, and I did not give him a second thought. I finally had the confidence to realize I was a quality girl who could have my pick of guys. I was the Chooser. I made it all about him, when it should have been me. The next weekend, I went out on a date with a super hot guy. The weekend after that, another date with another super hot guy. Of course, word got out to him that I had already moved on, and the little green monster did his thing. This man finally realized what he had and what he threw away. And after our two-week split, he actually came back and apologized.

Long story short, we did get back together. He had my heart but he had to earn back my trust. And he did – in time. Now he’s my husband.


Understanding men is a big mystery to women, but I have two great books for you. Both will help you in different ways. To Date a Man, You Must Understand a Man takes you through the basics of how the male mind works. I take you through all of those nuances and help you know what your next steps should be.

10 Secrets You Need to Know About Men is your man problem solver. I define 10 different traits most men possess and help you understand how you can counter the behaviors they exhibit because of these traits. I also give you the tools to turn things around – immediately.

How to Attract a Man: Avoid the Friend Zone!

How to Attract a Man: Avoid the Friend Zone!

2 Tips to Avoid the Friend Zone!

Avoiding the friend zone is easy if you do your homework.

I recently got an interesting and common email from a reader:

I don’t seem to have trouble getting dates and most guys who go out with me ask me out on a second or third date. My biggest problem is that the ones I REALLY like tend to put me in the ‘friend zone’ even if they are initially attracted to me and pursue me. Obviously, I’m doing something wrong here.- Cindi

I get many emails like this. When women go out with men they don’t really like, they tend to be themselves. They are cool in the situation, opinionated, and they challenge what is being said or offered. They show restraint when it comes to any sexual aggression.

This is all good because it piques a man’s interest. However, when a stunningly handsome guy pulls up in a BMW, women turn into these alien-like creatures their friends wouldn’t even recognize! What happens next is a chain of events that slowly and methodically erodes the attraction they both wanted.

How You End Up in the Friend Zone

To attract a man, you need to understand this – a man wants to be challenged. He wants you to engage him in new patterns of thinking. The man wants to be enlightened and hear her side on the subject at hand.

He also wants to hear about her interests and what her specialties are. If her only interests are reality shows and video games, it’s over. He is rooting for her, but she doesn’t come through because she is in such awe of him, that she agrees with everything he says. Sometimes this includes sex.

This is a turn off for a man and instead of feeling attracted towards her, he rejects her, or, if they work together or have mutual friends, he will put her in the friend zone.

BMW boy doesn’t want a yes girl, he has those already. This woman, unfortunately, turns into a Rest Stop and not a Keeper. Guess what happens next? Yup, he opens his file and places her into the dreaded friend zone.


Does this happen to you? I am going to offer you two suggestions to turn off this deer in the headlights response and have compelling subjects to discuss.

Avoid the Friend Zone! Desensitize by Practicing

Do this in your everyday life. If you have read The Social Tigress, you know you should be on the hunt for available men in your everyday life and not just during your allocated social weekend time. This should allow you to engage five or more men a week.

Challenge these men with witty comments and engage in conversation beyond just saying hi. Challenge that good looking barista at Starbucks. When you are out with your friends and feeling confident, challenge that good looking waiter or bartender.

See a cute guy in the elevator at work? Go for it. Say things like, “Great tie, I love how it matches your suit, but I would have gone with green.” You will love how he responds to your challenging comment and you might even get a date!

Avoid the Friend Zone!

Make a comment to the cute guy in the elevator!

The more attractive men you can engage in your everyday life, the better. The pressure is off and you can be yourself. Then, next time you are on a date with an attractive man, you will be conditioned to stay calm and act like your awesome self.

Fill your life with experiences

The more experiences the better. Experiences make you an interesting person – another trait men desire. By having lots of life experiences, you will always have something compelling to share. This will help you avoid becoming the yes girl because you will always have something to say and stories to tell.

Avoid the friend zone by following the two tips above and your success with men will be rewarded! For more tips on attracting men and avoiding the friend zone read chapter 12 in my best seller Love is in The Mouse.

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