When You ❤️ Love & 😬 Dating : A Recipe For Awkward

Navigating the world of dating is a lot like space travel. We know it’s possible, there have been great successes, but most of our attempts end in catastrophic failure. We’re faced with constant indecision, mountains of self-doubt, and somehow we’ve been tasked with tearing down the walls people have built around themselves. Despite the looming clouds above, we press on through the wind and the waves in search of the light.

The following is a collection of short thoughts compiled over the last year. They cover various aspects of love & dating but are not necessarily related to each other.

Society Tells Me I’m Broken

I’ve never really been that man that popular culture says we are, and I’m thankful for that. As a single man in my early 30’s I constantly feel more and more enraged with the words and actions of my own gender. I keep thinking if this is what women knows, that they expect. I certainly don’t fit in.

  1. Sow your oats young man.  I have married friends that are on a mission to cheat on their wives. Sometimes I feel like they only want to hang out so they have an outlet to hit on other women. As someone that chooses to be militantly faithful, I can’t understand why others can’t “man up and step up”. Someone choose to invest their life in you and it’s your duty to invest in them. Half the energy you spend avoiding your marriage would go a long way to building it. My single male friends that ask me questions like “Why don’t you just fuck the loose Tinder bitches like the rest of us?” Personally, I’m not one for “locker room talk” in fact, it really makes me want to punch people in the face. I constantly feel chastised because I’m not trying to add notches to my bedpost like it’s a video game. Sorry, but I’m not into creating a wake of hurt.
  2. The laws of attraction. Most men long for summer where bikinis reign supreme, I long for cardigans in the autumn air. (Why yes, I did notice your cute sweater. Indeed, I should’ve told you) Each to their own but I find tasteful modesty attractive in both dress and attitude. There is something magical to me about a woman that doesn’t feel like she needs to put it all out there all the time. I’m attracted to you, not your cleavage.
  3. Love like the movies. To both my credit, and my downfall I have a 16-year-old view of love. I do believe that love can be amazing, that magical moments exist and ultimately people are good. I believe it’s your duty to win you lovers heart every day in whether it a grand gesture or doing the dishes. Hey, there is no reason why you can’t take a helicopter to a mountain top picnic just because it’s Wednesday… and Wednesdays suck.
  4. Failure to launch. For a lot of men it’s easy, but asking a woman on a date or even asking for a phone number is incredibly difficult for me. The reason is two-fold. First, I am incredibly shy one-on-one. Something that has grown exponentially over the last year and a half, I’m working on it slowly, but for now… I really need to know you first. Secondly, I go out of my way to not inconvenience others. I never want to be that asshole hitting on a girl that is just trying to have fun with their friends, or give someone anxiety about how to reply. I’m stressed just writing about this.

Yes, I’m a man. I love sex, have a dirty mind, and desire the company of a good woman. I also value respect, dignity, and context. There is a time and a place for everything. Yet, I don’t fit in with the guys, and I can’t help but feel like I’m broken.


Lessons From A Tinder Dropout

Since it’s launch Tinder intrigued me. My life has not taken a typical dating path, and I’ve always been in long term relationships so I was curious what it’s like. Would anyone swipe right for me? What kind of person swipes right for me?  Is it possible to find something real on Tinder? So when I felt like I might be ready to date again I signed up, crafted a bio, curated my photo gallery and sent it to masses, so strangers could quietly judge my worth.

Screenshot_20161109-181107.png

My actual Tinder profile with bio version 2.0

I wouldn’t say that I struck out on Tinder per say. I had quite a few matches (I just installed the app to take the screenshot and still have 5 matches after months of inactivity) but I can’t say that any of them turned into actually meeting someone in real life. After a month or so of jumping down the rabbit hole, I decided to retire Tinder. Here are some insights from my journey in the Tinderverse.

Why I didn’t swipe right for you

  • Your photos look like a Where’s Waldo book. In a context where you are given so little to go on, photos are important. I want to see you and your personality.
  • Your photos span a massive timeline. Your profile should be about who you are, not who you were. My personal rule of thumb was to only use photos taken in the last year. Yes, I was skinnier two years ago but it’s not relevant now.
  • All of your photos contained alcohol or drugs.
  • Your photos portrayed smoking or heavy drug use (yes there was many).
  • You didn’t fill in a bio. If I have nothing to go on, our conversation is going nowhere.
  • Your bio was overly pompous or the first word was tattoos. Hey, I like tattoos too but if you’re not a tattoo artist they shouldn’t define you.
  • The quality of your photos made you seem like a bot or phishing scheme.
  • Your profile didn’t lead me to believe that we would have an interesting conversation.

Why I didn’t message you when we matched

  • When I reviewed your profile a second time I questioned what I was thinking the first time.
  • Upon review, your bio lacked enough information to have a real conversation.
  • My personal anxiety created a situation where I didn’t feel like talking then, but as a result, too much time had passed and I didn’t want you to think you were plan-b.

Why I unmatched you

  • I was always forced to lead the conversation.
  • You took too long to message back. Usually, 48 hours at first and timeline varies after initial contact based on the context of the conversation.
  • You avoided simple questions about yourself. If I’m going to meet you, I need to know something about you.
  • You seemed uninterested in learning about me.

How not to talk to women on Tinder

  • DO NOT seem genuinely interested in who they are or what they do. The more genuine you try to be on Tinder, the more people think you’re a creep. Even though their bio says “absolutely no hookups”, the majority of Tinder matches are expecting you to throw yourself at them.
  • DO NOT start a conversation with anything you would normally start a conversation with. You want to start with an interesting question or if you’re the brave type, a horribly bad pickup line.

Tinder was an interesting world I can say that. I know a lot of my list is superficial and subjective, but that’s exactly what Tinder is. I could tell our world was heading this direction when back in the 90’s every chat rooms conversation started with ASL????? The online conversation game annoyed me then, and the AOL chatroom has been reborn in Tinder.

Tinder isnt for me because I’m not into playing the field, I play for keeps.


There are two more sections I excluded for length. If you enjoy my ramblings about love & dating leave a comment below and I will consider posting them soon.

What are your experiences with online dating?

Have you had success? Failure?