It’s no secret that some guys think too much.

Believe me, when you’ve got a Type A personality, you rarely want to make things too complicated for yourself moving forward. The irony of this is that while you may have great plans and aspirations in your head about romance and dating, you probably have a good track record of sabotaging yourself.

Whether from the things you said or from the quirky things you do because you’re just so socially awkward, feeding yourself reasons to follow through with asking out a girl can be tough.

Honestly, there are some days where you would rather not even try because you know yourself too well. I am the furthest thing from a love expert, but I have some good news for you. As someone who’s been there, I’m here to tell you that you are not alone, and you are not crazy.

As a way of humoring myself, I will tell you about some interesting things that have gone through my own head as I decided the course of action I would take when I was smitten.

1. Does she like cats? Is she allergic?

Okay, so, anybody who follows me on SnapChat knows that my cats are like my children. I was raised with cats and so, I am that crazy cat person who daydreams about making Twitter accounts for his cats. The way a woman would interact with those two is a big deal. I mean, what if we moved in together? What kind of pets would we have? I like dogs, but would I be able to live in a cat-less home? What a nightmare that would be!

2. Can she cook?

Please don’t hate me. Let me explain, I’m not sexist. I just imagine the typical “Leave it to Beaver” kind of family where the wife cooks an awesome meal that the two of us can enjoy together. I’ll cook too, of course. It’s just that I sometimes think about who would take over in the kitchen. It’s not that I wouldn’t mind. It’s just that if she does, will I be able to stand her cooking? Will she be able to stand mine if it’s the other way around?


3. What kind of music would we listen to in the car?

I blame it all on my roots, I am a hardened country boy and that’s just the way I am. I have a strong passion for the country music of long ago and some of the singers who keep it country. I have no interest in Luke Bryan and Florida Georgia Line because I don’t feel like they are actually country. Now, if this girl I may talk to does have a preference for these types of artists, then it’s an automatic deterrent for me.

I think about what a car ride with this woman would be like, if she would want to blast Luke Bryan, or maybe she is into hippy music, and really likes Jimi Hendricks. Rap is also an automatic parasite of my interest. I love older music, so, would she be able to sit through “Walk Through This World With Me” by George Jones? Would she want to change the station, for those of us who still listen to the radio? What version of “Landslide” does she prefer? The original by Fleetwood Mac? The one by The Dixie Chicks? I kid you not, I think these things out sometimes.

4. Is she a Christian?

Kind of piggy-backing off of the last one, I think just being able to listen to worship music is super important. More important than my musical preferences, is my ability to maintain and grow my relationship with God. I wouldn’t want for a woman to be disapproving of my lifestyle. I don’t drink, I don’t smoke weed, and I don’t gamble.

So, this isn’t just about if she has a problem with Jesus, as it is about if she has a problem with my life because, at this point, the two are one and the same. I consider what cultural and religious differences or barriers I would have to overcome to make it work.

5. Will she mind the way I talk?

I think many guys have this thought and just don’t register it. Some folks have a problem with the way their voices sound, and that’s normal. There are a lot of dialects in the world, so it’s no surprise that a lot of us are awfully aware of our speech patterns. I, for instance, have two accents mixed together in a cocktail that even I don’t understand sometimes.

At one end, I have a Canadian-accent from my grandfather and uncles. At the other end, I have a semi-Southern accent that I picked up from my stepfather which helps me with singin' country music, but gets annoyin’ when I’m talkin’ to people but my mind is just listenin’ to how weird my friggin’ accent sounds. I also stutter or mumble sometimes, which can also be a big block between a potential date and I. For the most part, I’m proud of my accent because it’s unique. Yet, I think about how a woman may perceive it. I hope she would have a sense of humor, at least.

6. Will she like my puns?

I’ve gotten to the point where I’m using puns as a way to divert, or sometimes create, a conversation. I will usually start off with a light-hearted pun that was relatively well thought out. My company will usually laugh at it and commend me on my sense of humor. Then, I will bring out more puns, until I eventually snowball into a mess of sorts where I can’t seem to let situations go by without breaking out into Comedian Rich Mode. This form of me has a tendency to keep the puns coming.

I tell myself to take it easy with my pun usage before the moment of truth when I approach a woman. If I did let one slip, I would make sure it was around some trees, so I could ask her if she wants me to leaf her alone. I wouldn’t want to "treet" her that way. Now, you’re beginning to understand as you read this. Sorry, I can’t see the root of the problem.

7. Will she mind the fact I'm not muscular or athletic?

We all go through phases where our self-esteem just tanks when we think about how we look. It’s natural. We tend to notice our imperfections better than look at the big picture. For when we see ourselves as healthy and we see that we are where we need to be with our physiques, we can block out the negative perceptions of others. People will tell you that women want a guy with a six-pack and that you should do “curls for the girls.” What do you do though, if you barely eat or if your body-weight percentages are too much for washboard abs just yet? What if the last time you visited a gym was to use their bathroom? What if I get more enjoyment out of playing Super Smash Bros.?


Now, I work at a gym, so I have the resources to stay in shape. The problem is the space in between when you want to work out and the body a woman may prefer. Changing myself for a woman never seemed too important or beneficial to me. The way I see it is that God has me the way I am for a reason. He loves His creation just the way He designed him. Still, that doesn’t mean I don’t consider how a woman would view my 12-minute mile. Will she like me more when I get it down to a 7:50 mile? I don’t know what her expectations are. I haven’t even met her yet.

8. Would my friends approve? Would she approve of them?

Along with your family, your friends are, for the most part, a package deal with you. I think we’ve all had that one friend we’ve basically “lost” to their new relationship. It’s been a while for me, but from what I’ve surmised about relationships, they require a lot of time and attention. The problem is in how I would be dividing my attention with a woman in the picture. I don’t like the idea of changing myself for people, and that includes changing who I decide to be friends with. With that being said, I’ve made a lot whose opinions mean a lot to me. Some of them know me better than I know myself. So, I would put my trust and respect in their judgment. At the end of the day, I would be making my own decisions but ultimately, I know I can’t just think about how something will affect me.

9. Will she be able to handle good, old, complicated me?

Confidence can be scarce at times. The only confidence we have at times is that we are too much work for a woman to handle. We think of our demons, our quirks, our habits, and our beliefs. We wonder if they are just too heavy or annoying for this person. We don’t want to offend or scare her off, so we wonder if we should even begin this “asking out” process. Will she show interest at first and then get tired? Will she laugh and treat me like a lower-species? Is she expecting a cookie-cutter man who fits her own personality? Well, this is another one that I’ve learned to get over.

The factors about me that make me “hard to handle” are my strengths at the same time. They don’t have to have the same, glossy coating as peoples’. It’s not up to her at this point. It is up to her if she wants to accept me for my horns and wings. Whether I have a collection of Naruto volumes or not, or if I walk everywhere I go should not matter because, at the end of the day, I would want her to take me as I am.

So, I guess the big lesson here is that we are way too prone to overthinking situations that could be so much easier. We think about the future, whereas the act itself exists in the here and now. There’s nothing to fear, as crazy as that sounds. It’s like pulling off a bandage. You just have to commit to it and do it. Don’t worry about how you come across and all the unpleasant things that she may see in you. Sometimes, she’s really just worried about those same unpleasant things you may see in her.