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Have you ever met a guy out one night, had easy-natural conversation, a couple good laughs, and the spark of a little good old-fashioned chemistry, but still you left without a date, without exchanged numbers—without anything really?

Well, I'm here to admit that more often than not I've been just the type of guy on the other end of that promising but fruitless exchange. I'm the guy who leaves you asking your friends at brunch the next day: "Am I crazy? Was it just me?

As I understand it, this whole scenario confuses women, causes them to doubt their feminine intuition, and can even make a woman feel used. But the truth is, more often than not, my reasoning for not asking someone out had nothing to do with them. Today, I'm engaged to a great woman, but before meeting her, I met a lot of women who might have had potential, but I never got things off the ground. Here are five hangups that likely explain why I (and a lot guys) are guilty of leaving women dazed and confused. 

01. I was dealing with insecurities.

Unsurprisingly, the likelihood of me asking a girl out often correlated with how I felt about myself.

Just like many guys, my self confidence wavered significantly throughout my early- to mid-twenties. There were times where I thought I had it all together and that every girl would be happy to go on a date with me. But at other times, I didn’t believe that anyone would ever want me.

This isn’t something guys like to admit, but if we aren’t feeling great about ourselves, then we are way less likely to assume that the woman we are engaged in a wonderful conversation with is actually interested in us back. Not only that, we are less likely to want to be in a relationship with a woman when we don’t feel like our best selves because we want to give our best.

02. Guys have a one-track mind.

Have you heard about the male brain and how it’s made up of lots of different compartments? Brain research explains that we tend to process information by focusing on one thing at a time. Comedian and marriage speaker Mark Gungor describes this as having a brain full of boxes—one for work, one for conversation, one for sex, one for food etc.—and, as Gungor explains, these boxes can’t touch. Honestly, this is why sometimes a guy can have a great conversation with a woman and not ever think about asking her out.

I know there have been many times where I have met a pretty and nice girl, and the only thing that I thought about was how much I liked talking to her. I wasn't thinking about a date; I wasn't thinking about calling her; I was literally just thinking about the conversation here and now. This happened early in my relationship with my now fiancé, and it almost cost me a second date with her.

One night, shortly after our first date, she and I stayed up until 1 a.m. messaging each other. When she was finally at the point of exhaustion and had to go to bed she said “next time you want to have a five hour conversation, let’s do it in person.”

Of course, I immediately asked her out on a second date, but until that point I honestly hadn’t even thought about seeing her again. I was only thinking about how much I enjoyed talking to her.

Lucky for me she was thinking about multiple boxes at once.

03. The timing was all wrong.

There have been many times over the past several years when I just wasn’t in a “good place.”

While I was contemplating quitting my job in Chicago to travel, I met a few girls and had great conversations with each of them where we discussed the many things that we had in common. At this time my confidence was at a healthy level, so I could sense that they were interested in me, but since I was considering making a huge change, I knew pursuing a romantic relationship with them wasn’t the right thing to do.

Ultimately, I did decide to travel (which luckily ended up leading me to my current fiancé), but even if I hadn’t, it wouldn’t have been right to go out on a date with any of the great girls I met. My mind was elsewhere, and I could never have committed to any of them during that time.

04. I assumed she was already involved.

Despite what this has sounded like up to this point, I have asked many a girl out. And many of those girls turned me down because they already had a boyfriend. 

Once, while at a restaurant in New Zealand, I met a really nice girl from Ireland. She had beautiful eyes, was charming, and had a lot of interesting experiences to share with me. By the time our conversation was coming to an end, I felt like I could see our future together.

When I asked if I could see her again, she told me she had a boyfriend. In fact, he was at the restaurant with her, sitting at another table with some friends.

Even though I never took situations like this personally, rejection still sucks. Experiences like this lead me to, at times, assume every great girl must already be taken. Therefore, even when I had a really great conversation with a girl, I would resist asking her out. It may have been silly of me, but a guy can only get his hopes up so often.

05. I realized that it wasn’t going to work.

Even during a great, interesting, and engaging conversation, sometimes I could just tell that things would not work out between a girl and myself.

It was more than just intuition. Oftentimes I would learn things about the other person that are deal breakers or other reasons that made me hesitant to pursue a relationship. For example, as a natural introvert, I’ve learned that it is very difficult for me to be with someone who can’t carry more than their share of the conversation. So even if the conversation went really well, if there were too many times where I felt like I was doing the majority of the talking, then I might feel less inclined to pursue. And that has nothing to do with the girl. I think it is great for a girl to be introverted, just like me. But after years of dating I realize that other introverts and I aren’t meant to be in a romantic relationship together.

It's important to remember that, if a guy confuses you by acting totally into you and doing nothing, you are not crazy and you probably didn't do anything wrong. But, by the same token, there may not be something wrong with him either...he may have a justifiable reason for letting you slip away. 

Photo Credit: Cynthia Chung Photography