How Christian Men can be Challenging and Attractive on Dates

This article is the expected follow up to One Thing Never to do Around a Woman.

There are two reasons for this follow up article:

1. To show you how to be more challenging in your social interactions and dates. A challenging man is more interesting, fun and attractive to high quality beautiful women. High caliber Christian women are bored with average guys and their average ways.

2. To explain how not to be an overcompensating jerk or annoying pest. Trying too hard will kill any chemistry you have or could potentially have.

Let’s start with the good stuff first.

1. So you want to be more challenging in your social interactions – particularly with a woman you are romantically interested in – but you don’t know how.

Try being more interesting, playful, fun and challenging. Create a positive vibe that makes interactions fun. It’s kind of like you’re playing with your little sister or cousin – but you are adults.

So you don’t actually treat the woman like a child, but the dynamic is “I’m the older brother that is teasing and playing with you. I care about you so I don’t want to hurt your feelings, but I’m not afraid to poke fun or joke around with you.” That is an excellent way to frame an interaction with a woman.

For example, let’s say you are at a social gathering. It could be a birthday party, church mixer, or whatever. You find yourself in conversation with an attractive young lady and you’d like to know if there is more to her than her pretty face. You go through some introductions about who you know, or why you’re there, and then…

Her: “So what do you do?”

She is showing interest farther than just  a superficial level and is asking for you to add input into the conversation. It may be a sign that she is being polite, has social awareness, is being friendly, or might even have an interest in getting to know you more. For now, we’ll just presume she is being polite and friendly.

You: “I’m an agent for Acme Car Insurance. How about you?”

Her: “I’m a teacher.”

You: “Oh, that’s so cool. I commend you for that. Do you like it?”

Her: “Oh, thanks. Yeah, I love it. I’m glad I got into teaching.”

You are not the first man in the universe that she has asked “what do you do?” but you definitely are just another average guy if you reply in an average manner like that. Average equals lame and boring. You don’t stand out, and you didn’t do anything to be challenging, interesting, or fun.

Here is what you could have done:

Her: “So what do you do?”

You: “Well, I come to the rescue of bad drivers. In fact, I think I’ve seen your file a few times, you have a lot of reckless driving tickets, don’t you.”

You tease her a little, but she laughs because you are obviously just joking and trying to have a fun, light conversation at this social function. You don’t directly answer her question and you indirectly ask her to “play your game”. Now if she responds in any way that is positive, that means she is down to play your “game”.

Her: “Haha! What!? No way! I’m such a good driver! Are you a cop?”

Her response is positive. She is having way more fun already than the boring conversation she usually has with every average guy.

You: “Whoa. Do I look like I like a disciplinarian? No way. Try again.”

You are being fun again. Lot’s of playful tonality and smiling so she knows you are being light hearted.

Her: “Haha. Ummm, are you a lawyer?”

She is playing along. Interested to keep the conversation going, and having fun. You have presented two challenges to her by basically saying, “Guess what I do.” If you continue to make her guess, it might get annoying or come off as jerk-ish.

You: “Whoa, whoa. First I look like I’m a disciplinarian, and now I look like an arguer? Man your mean! I’m a car insurance agent for Acme. How about you? You must be a judge or something considering you guessed I was a lawyer and cop.”

Again, you must communicate that you are being light hearted and fun by smiling and keeping high energy. The entire dynamic of the conversation changes based on just a little challenging comment or two. She had fun, she is interested, and you instantly stand apart from every other average guy.

The idea is to put up a little resistance to her inquiries, requests, etc. not to completely avoid or ignore them. That’s just annoying. Which brings us to the second point.

2. Challenging does not mean to be an overcompensating jerk or annoying pest. No woman will become romantically interested in you if you are challenging just for the sake of being challenging.

The point of putting up a little resistance is to make her work to earn your involvement. Beautiful women are always getting what they want. By teasing, joking, and generally just treating her like a guy-friend, you are doing something that she doesn’t experience with the majority of guys she interacts with.

But don’t take it too far – for example if a man were to take our conversation, and do this:

Her: “What do you do?”

Man: “I’m a butt model.”

Her: “Haha! Yeah, I can tell. Really, though. What do you do?”

Man: “I’m actually head french fry chef at McDonalds”

Her: “Haha. Okay, Mr. Jokester. But really…”

Man: “I’m a secret agent for the CIA”

Her: “Okay…”

At first, the funny “butt model” joke was challenging and the man set himself apart. But going too far is just annoying. The woman is showing genuine interest and wants to know more about the man, and he just keeps being challenging… too challenging. In fact, it’s jerk-ish behavior.

The idea of being challenging is to put up a little “wall” to her questions, requests, etc. by not immediately answering her question, or not quickly fulfilling a request… but the “wall” is not a permanent barrier… if she pushes back, then the wall should fall down and she should win your attention.

So don’t be a jerk or pest by being overly challenging. The Romantic Hero is a smooth blend of heart and spine. He isn’t a macho jerk, nor a wimpy nice guy. He is a challenging and interesting combination of each extreme.