I remember a time when meeting someone who was just as damaged was a bit of a relief. Everyone walking…
The pitch in her voice began to escalate. The words were coming faster and faster in frantic disjointed sentences. The…
She went to bed earlier than I did. A little hold over from her time spent in corporate America and…
I remember a time when meeting someone who was just as damaged was a bit of a relief. Everyone walking…
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The pitch in her voice began to escalate. The words were coming faster and faster in frantic disjointed sentences. The…
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She went to bed earlier than I did. A little hold over from her time spent in corporate America and…
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There is a sadness that seems to be constantly looming. Our brief periods of elation and splendor are consistently ruined…
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I can’t for the life of me remember where we even met. Clearly from online dating but which platform and…
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I used to pride myself on the company I kept. “Your friends are a bunch of assholes.” I would laugh…
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Someone once asked me, “How do you know when you are in love?” I responded the way you probably would,…
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I have always been fascinated by transformations. The desperation and tenacity of the human spirit is fascinating. I am magnetized…
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The moment we connected is lost to time. You are born with a limited amount of space and as the…
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My grandfather was a kind and gentle man. He was kind in the way TV grandfathers treat their grandkids on…
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So I guess this is a good time to let you all know that I will be shutting down the…
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“I had to leave because I went through all the women in that town,” she said. She probably expected me…
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All I could think was, here we go again. Having the same conversation over and over. I just wanted to…
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She hopped in my car as fast as possible while trying to escape the rain that was coming down in…
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I knew I could get away with it. The things I was shouting. The way I was embarrassing her in…
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I was sitting on the couch in my sweatpants catching up on my DVR when my phone lit up. I…
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First, I want to begin by apologizing for my lack of articles. This past week was one of the most…
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We had been talking for an intense twenty minutes. It was short ride, and I looked down at the map…
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In the summer of 2014, I set out to interview cheaters. Men, women, bi, gay, straight, black, white, young, old,…
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She stared at me with contempt. Furrowed brow, pursed lips, squinting eyes. It wasn’t playful. It wasn’t endearing or adorable,…
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We were lying in her bed watching the storm roll across the buildings. The view from her 52nd floor apartment…
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She asked to meet at a local bar near her house. She needed to be close to home in case…
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Everyone in high school was convinced they were going to marry their boyfriend or girlfriend, and I was no exception….
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It was a beautiful summer day so we sat on the outdoor patio. Surrounded by the downtown buildings and occasional…
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She had these odd weathered hand-stitched tapestries on her wall. Three different pictures of sad looking clowns on what was…
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I used her. She didn’t even know it was coming. She didn’t even tell me her real name, but she…
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Since when is sex the “ultimate” form of love and why do we all just take this as gospel? The…
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Through all of my mis-adventures with internet dating, I have learned that a vast majority of women love to cuddle….
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He said, “I just wish I knew why she keeps going back to him.” We drove south on Lake Shore…
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I know it seems like things are always rough but this time right now might be one of the roughest….
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Unseasonably warm for fall in Chicago, I rode toward Racine Avenue slowly so I wouldn’t sweat. My eyes still puffed…
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No one truly knows why we like what we do. After meeting over a thousand people for a date and…
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It really is an interesting thing to look at if you step back for a minute – this life we…
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Just Another Coffee Date An excerpt from my book Maybe He’ll Grow Out Of It I put the condom in…
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There is a series of unspoken questions you go through online before most people agree to meet in person. Generally,…
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When he walked through the door you were intrigued that someone so charming would find you attractive. Or maybe you…
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We had agreed to meet downtown on her lunch hour for coffee. She showed up in a blazer and sensible…
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I have a confession: I am a recovering Fuckboy. For those of you who don’t know the definition, just do…
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Glamour Magazine wrote a very famous article on the things a woman should have and know by 30. It inspired me…
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She sat across from me visibly uncomfortable. Eyes darting around the room then resting back at her shoes. The way…
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One of the great things about being an adult is the fact that we can do whatever we want to…
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She sent me a text, “I’m such a loser.” “Why do you say that?” “Because it’s Saturday night, I shaved…
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I don’t hang out with children all that often. I don’t have any, all my friends that do live out…
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It was a shot in the dark. I sent her a mildly flirtatious email and crossed my fingers. To my…
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The equally great and awful aspect of internet dating is the fact that you can be practically anonymous. Sure, you…
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He threw his hockey equipment in the back seat, closed the door, then hopped into my passenger seat and asked…
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Nine years ago I flew out to Colorado to give a speaking at a university. Thus began my years of…
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There is a disconnect between generations. And while age does play into this, it is not entirely exclusive. My mother…
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Last week, I wrote an article referencing a story I wrote in my book, The Direction Of Home. The story…
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There was an air of superiority in her tone. Something that comes with being exceedingly successful in one’s career but…
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As we stood in the freezing roller coster queue on my first date ever, I thought “either we’re getting married…
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I remember waking up and my mom rushing into my room and sitting down and saying, “Listen, I know you…
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Under the El tracks in Chicago, I once met a woman for sex in the front seat of a car….
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One of the few things that I think a lot of people misunderstand about dating is expectation. From the first…
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While I was writing my dating profile, I told my roommate I would meet up with anyone who asked. Finding…
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I guess what you never really expect is that you never forget. Over the past week, I have been going…
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I opened my laptop today to do my writing and I noticed that I didn’t close out of the PDF…
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It has been a while since I have been deep in the belly of online dating. But like summer camp,…
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Her initial opening email made some mention about my online profile in reference to something I wrote about how you…
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She literally jumped into traffic to win me back. As I rode in the passenger’s seat to see her for…
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I read an article recently that mentioned a theory about how as we grow older we lose more and more…
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It has always been about what I could get. I mean, even my first girlfriend was more about social status…
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I was talking with a friend last night about her recent troubles and this story came up. Instead of rehashing…
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She sat across from me nervously tugging at the bottom of her striped top. I knew the motion. She was…
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He stood across from me, eyes transfixed on the passing traffic. He wasn’t pausing for dramatic effect, he was visibly…
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With my high school reunion coming up, all of a sudden tons of old pictures are coming out of the…
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Four times in the past couple weeks people have said that I look 27. When I tell them how old…
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I don’t know if I have mentioned this on here before but in my spare time, I sometimes drive for…
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It was rainy Saturday night in Chicago. I drove slowly down Clark Street doing my best to avoid the zombie…
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There are thing that are going to happen in your life as you grow up. You will realize that you…
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The entire motivation for starting this site was to put something positive back out in to the world. It was…
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It’s one of the few commonalities we share. Love and the loss of it impacts almost every person at every…
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I want to follow up the entries by Chris (Managing The Crazy) and Sarah (Defending The Crazy), as I have…
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We constantly hear people talk about how they always tell the truth or how they just want to hear the…
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Throughout my life I have always kept a moderate to barely above average exercise regiment. I have my slow months…
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I recently received an email asking me for suggestions on how to help someone connect more with her boyfriend. She…
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I am a naturally curious person. If you have ever had the displeasure of sitting across from me over coffee…
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I pulled the baked potatoes out of the oven and placed them on the table. She called from the other…
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I was sitting in the back lounge when he came on the bus. He was loud and obnoxious but with…
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When she called and said that she wanted to break up with me I simply responded with “Okay,” and then…
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As a woman and a “reformed crazy girl,” let me be the first to burst your bubble: The perfect woman…
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Like you, I was raised with unrealistic expectations. The ideal of the perfect person is sold to us through movies…
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I remember him leaning her up against his red Ford Escort that he had bought himself from working at his…
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He walked in the apartment visibly upset. Without saying hey to any of us, he kept his head down as…
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I’ve been an awful fuck most of my life. When I was a kid, like most kids, what other people…
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I don’t remember exactly which website it was, but I do recall how intriguing I found her profile. She was…
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We had been dating for a few months and had somehow made it past the period of being a simple…
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After telling someone you’ve been on over one thousand first dates, you can expect to be asked some questions. Some…
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I have been in some form of a romantic relationship for the majority of my life. It began in 8th…
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When I think about it, there have been very few people I have come across that have genuinely shook me…
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She told me she was moving across the country for him. When she left two years ago, she said that…
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We were driving along Lake Shore Drive and the waves were crashing white. It was about midnight and we were…
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I had to have been around 21. Our little group of hoodlums sat next to a table of adorable girls…
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Time has always been a constant theme in my work. It’s time to get going. It’s time to make a…
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If you’re like me, most of your relationships have failed. Maybe some were your fault, but let’s be honest –…
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I will be leaving for the airport in a few hours, then after a bit of a pit stop in…
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Tuesday, December 1st, 2009 4:58 am. 5am. i finally washed your smell off of my pillows tonight. then i died…
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Tonight, Bruce Jenner went on television and made his (he did say that until he emerges as a woman he…
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Today, I was asked to respond to this question for a website: “Basically, if you are going to do the…
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At first I thought it was a joke. Like the way you say things in the heat of the moment,…
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There are vast expanses of the country that don’t receive cell phone reception. Miles upon miles where you are forced…
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I always dread birthdays. Not because I fear arbitrary milestones or the number of times the planet has made it’s…
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Our lives only seem easy in retrospect. When I look back at my life I would like to think it…
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I always say you have to give it a few years to let the wounds heal, but eventually, provided you…
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It was late, probably two or three in the morning and my depression was weighing heavy. In retrospect, I can…
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Okay, so I had an idea for an article tonight but I as I was outlining it over in my…
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I have done my fair share of awful things in relationships over the years. I won’t go into too much…
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In my past article, I mentioned that I wasn’t an easy person to date. Sure, I’m abrasive and opinionated like…
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She told me she couldn’t say his name for years. That when she was on the train or in a…
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For part 1 of this, click here The break up followed two weeks later. It was perfect timing because after…
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I pulled up in front of the West Loop wine bar and waited. After a few minutes, an attractive blonde…
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This is an article I published a couple years ago but after some recent conversations, I feel it need to…
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The older I get, the more I realize just how little I know. More specifically, how little I know of…
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Last night I drove out to the suburbs to hang out with my brother for his birthday. He had a…
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I never intended it to be anything serious. I found her social media profile online and was blown away by…
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We had gotten a pretty big group of people together to go to the movies. From what I remember it…
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In the summer of 2014, I set out to interview cheaters. Men, women, bi, gay, straight, black, white, young, old,…
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The problem was, I put her on a pedestal. Not that she didn’t deserve the utmost respect and adoration, but…
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She asked me, “Do you think I will ever want to settle down?” I knew she wanted perspective, or even…
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I guess the most important aspect of my relationships didn’t come to light until fairly recently. See, I have always…
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He was tall, handsome, and built. He had a deep voice, confident gait, and perfect hair. The kind of guy…
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She yelled, “But you promised you would never leave me.” And she was right. I did say that. And I…
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I never liked generalizing people. And while stereotypes exist for a reason, the problem is – they simply aren’t exclusive….
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I have always maintained the the key to a happy life is the ability to continue to evolve. Stagnancy is…
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I am notorious for over-booking. At least once a week, plans will overlap with other friends and I look like…
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Like I have said before, there is a difference between what we need and what we want out of a…
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I get it. I have been there plenty of times to see it coming and to know when I’m deep…
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In the summer of 2014, I set out to interview cheaters. Men, women, bi, gay, straight, black, white, young, old,…
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I often talk about my time immersed in online dating. I speak about it in the way that people reminisce…
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So I started a podcast over four years ago to answer the questions people had been asking me about sex…
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It was a beautiful sunny day in Chicago yesterday so I walked over to my local Starbucks and ordered a…
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I had some time on my hands and decided to help organize and clean my moms basement. While my mom…
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I’m naked. Stark. Ass. Naked. And, I’m in the “quiet room,” although, they might as well call it, “time out…
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I walked into my managers office and asked if if she had a few minutes to speak. I sat down…
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I sent him a text asking him how he was handling the break up and he replied, “She made the…
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A few times a year, mostly when it’s late and I have run out of things to look at on…
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She sent a text asking if I would be able to meet for coffee. I said sure and that I…
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There are few things that give us away more than our subconscious. Sometimes when I get stuck on writing I…
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She said, “I would totally date you… if I didn’t know about your past.” It’s not like I wasn’t aware…
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I looked at him in the mirror of our tiny bathroom while he fixed his hair. “You are so handsome,”…
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In the summer of 2014, I set out to interview cheaters. Men, women, bi, gay, straight, black, white, young, old,…
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My first real job – one where I wasn’t being paid under the table or being exploited for underaged labor…
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I’m the product of a teenage pregnancy. My mom was a 17-year-old high school senior who was desperately in love…
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“I just don’t understand.” She said, “What kind of person would text a breakup?” “A coward.” I said. “All he…
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1. Please touch us Cuddle us, spoon us, grab the small of our backs. Kiss our foreheads and make us…
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“My life was amazing before you and it’ll be amazing after you.” It’s what I should’ve said that. And 2…
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When I read how people claim to have no regrets, I always sigh and shake my head a bit. Sure,…
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I picked up the phone to call for the third time. Her parents kept telling me that she was out…
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Since her online dating profile only had a few pictures, I sent her a text asking if she had any…
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I guess I would consider myself lucky in a way that my questionable life choices have provided me the opportunity…
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We slowly walked up the concrete steps of the industrial building in one of Chicago’s up and coming neighborhoods. It…
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We were sitting on opposite sides of the couch facing each other. I pulled the red blanket up to my…
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It happened so long ago but I could still take you back to the exact parking spot where I lost…
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“Sorry, Mom. Sorry, God.” –‘Invisible Monsters’ by Chuck Palahniuk My hands shook in time with my racing heart. “Before…
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It took months, but eventually one morning I rolled over and before she could even say good morning, I said,…
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My phone lit up as the text came through, “There is no way you went on a thousand dates.” She…
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There was never a woman more intriguing. I couldn’t believe she responded to my messages let alone allow me in…
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Every person we encounter is different. Even if there is nothing noticeably unique about their character when we meet them….
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I have been online dating since I first learned there was a way to semi-anonymously contact another person online. I…
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I once wrote a story called Less Than 35. A sad, self-serving, tale about doing my best to stay alive…
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It’s weird being a dad. I never expected to like this job. Not even close. When my then girlfriend (now…
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She was blocking the door with her body. It wasn’t even crying anymore, it was more of a hyperventilating heaving….
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I think we both knew the relationship had been over for months. It seemed that we were just waiting for…
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“Oh, I know someone I could set you up with.” I said. She looked at me with pursed lips and…
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I was just trying to drink my coffee in peace but my local Starbucks is always so overpacked that it’s…
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I walked past the shops looking at my reflection in the windows wondering if I had made the mistake of…
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I often wonder how different I would have turned out had social media been around when I was at my…
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They would say, “But I just don’t know how to tell him.” And I would always respond, “Just tell him…
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Ever since I mustered the confidence to speak to people, I have seemingly been on a continuous search for the…
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In the mid-90s, my friends and I would make the 20 minute journey, two towns away, to go get coffee…
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We have all heard the saying that there is a difference between words and actions. And it’s pretty simple. There…
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Once you realize the influence you have on another person it is difficult to suppress the desire to abuse it….
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I guess I grew up around enough people with an entitled attitude to have learned to steer clear of expectations….
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As we age, it is nearly impossible to avoid gaining knowledge and insight into the world around you. Well, to…
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In the summer of 2014, I set out to interview cheaters. Men, women, bi, gay, straight, black, white, young, old,…
Continue Reading ...
We met downtown for overpriced coffee. We chatted and discussed the ridiculousness of our past relationships. For as much as…
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I knew she had been drinking. Not to the point of being sloppy or belligerent, but just enough for her…
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I am not easy. It took me a while to understand this, but eventually after years of long talks and…
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I think one of the most defining moments as a man is when you realize you actually do owe something…
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We hear all the time about how important self-confidence is to our growth. It seems to be the catch-all for…
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If you’re here and reading this, odds are you want what most of us desire. To be in a happy…
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Her hand kept tapping her empty cup on the metal table. “It’s like, I just keep telling him what to…
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She was one of the first strangers I met from the internet. I’m pretty sure we found each other on…
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One of the biggest mistakes people do when attempting to console a friend after a break-up is to tell them…
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I rolled on my side and wrapped my arm around her. I nuzzled my nose into the back of her…
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I asked him how his relationship was going and he said, “Eh.” Just a simple grunt of a response but…
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I wondered why she didn’t come around much anymore. On the weekends, my mom would leave to visit her boyfriend…
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My friend was new to online dating. We texted back and forth about the emails she had received and laughed…
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Maybe because it’s late and maybe it’s because it’s a warm summer night and nights like these remind me of…
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Have you ever been with someone you didn’t trust? A boyfriend or girlfriend. A brother or sister. A friend or teammate….
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Each one of us was born with some thing or some one doing it’s best to hold us back. None…
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So how will you make it? You make it by changing the way you see it. The break-up will be tough….
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I was listening to her talk. She was emotional and I could see the tears welling up in her eyes….
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The problem is, we are constantly looking to be inspired. We are so susceptible that even when we’re not paying…
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I watched the red tail lights zoom away from our house and fade into the evening darkness. I looked back…
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I remember a time when meeting someone who was just as damaged was a bit of a relief. Everyone walking…
The pitch in her voice began to escalate. The words were coming faster and faster in frantic disjointed sentences. The…
She went to bed earlier than I did. A little hold over from her time spent in corporate America and…
There is a sadness that seems to be constantly looming. Our brief periods of elation and splendor are consistently ruined…
I can’t for the life of me remember where we even met. Clearly from online dating but which platform and…
I used to pride myself on the company I kept. “Your friends are a bunch of assholes.” I would laugh…
Someone once asked me, “How do you know when you are in love?” I responded the way you probably would,…
I have always been fascinated by transformations. The desperation and tenacity of the human spirit is fascinating. I am magnetized…
The moment we connected is lost to time. You are born with a limited amount of space and as the…
My grandfather was a kind and gentle man. He was kind in the way TV grandfathers treat their grandkids on…
So I guess this is a good time to let you all know that I will be shutting down the…
“I had to leave because I went through all the women in that town,” she said. She probably expected me…
All I could think was, here we go again. Having the same conversation over and over. I just wanted to…
She hopped in my car as fast as possible while trying to escape the rain that was coming down in…
I knew I could get away with it. The things I was shouting. The way I was embarrassing her in…
I was sitting on the couch in my sweatpants catching up on my DVR when my phone lit up. I…
First, I want to begin by apologizing for my lack of articles. This past week was one of the most…
We had been talking for an intense twenty minutes. It was short ride, and I looked down at the map…
In the summer of 2014, I set out to interview cheaters. Men, women, bi, gay, straight, black, white, young, old,…
She stared at me with contempt. Furrowed brow, pursed lips, squinting eyes. It wasn’t playful. It wasn’t endearing or adorable,…
