Gary

Part of the reason why I have subjected myself to the tortures of on line dating is for the simple experience of actually going on dates. Having never dated until my mid twenties, my Dad once assured me that dating was meant to be a "fun" past time. Since Dad was the ultimate bachelor, I figured there had to at least be some truth to his perspective.

"It's like you are 16 and just learning how to date" Evelyn analyzed one night as we sat on her couch, wine in hands.

"I know. I feel a little pathetic" I admitted. I was having to navigate dating etiquette, social cues, and awkward kisses for the first time. I had been in a series of monogamist relationships since I was 16. I could only recall the familiar feeling of falling in to a relationship, not the foreign thrill of falling in to love.

"I'm determined to just date a lot of different kinds of people" I told Evelyn. "I just don't know what my 'type' is. That is, if I even have a 'type'."

"Well we at least know your 'type' is not a meat head, now don't we?" Evelyn joked.

"Cheers to that!" I said, touching my glass to hers.

I had agreed to meet Gary for afternoon coffee. Having been on a few dates recently that lacked intellectual stimulation (to put it nicely) I was turning to my gut this time. Gary was tall, dark, and handsome but also seemed to be a touch nerdy. The truth of the matter is that I had always had a soft spot for men who had a little geeky streak in them. It may have had something to do with my creepy childhood obsession with Patrick Dempsey in the 1987 cult classic "Can't Buy Me Love" . Regardless, I found Gary to be endearing. I was looking forward to checking out Mr. Sincere.

I sat in my car touching up my lipgloss as I saw Gary walk in to the coffee shop out of the corner of my eye. I didn't get a good look at him, but I could tell it was him from his dark hair and preppy ensemble. I hopped out of the car and followed him inside.

It had been several dates since I felt the jitters that once overcame me before actually meeting someone in person. I had adopted a realist perspective after encountering so many bad matches. The reality of the situation was that I would perhaps meet a nice person who I could have an interesting conversation with. That was the extent of what I had hoped for walking through those coffee shop doors.

"Hi Gary!" I greeted him as I saw him standing in line. He smiled at me and said "Hi". His voice was timid and quiet. I instantly knew that my pre-date assessment was accurate.

"How has your day been so far?" I asked him in a bubbly tone.

"Fine" He responded quickly.

"What have you done this morning?" I continued. I uncomfortably focused my eyes forward. There were four people ahead of us and the line was moving at a snail's pace.

"Not much" Gary replied. I smiled and looked to the side. This was going to be challenging.

"Do you think you could make me a cup of French press?" A boisterous lady in the front of the line asked the barista. "But I want it to be really strong. What is your strongest roast right now?" She continued.

"Let me check on that for you" the barista replied and went into the back to search for the lady's request. I took a deep breath and slowly let it out through my nostrils as I bit my lower lip. Gary stood next to me with his hands in his pockets, slightly swaying back and forth.

"I'm just going to jet into the bathroom quickly! Feel free to order and I'll meet you at a table." I told him as I was already walking away.

I locked the door behind me and faced the mirror. I had never met someone who didn't at least try to talk to me. I had definitely been in situations where the conversation was one-sided, but there was usually at least a small effort being exuded from the other party. I clutched the sink and leaned forward, in pep talk position. "You can do this, L.A. It's just coffee." I ran over a list of conversation starters in my mind as I looked at my own eyes in the mirror. I took another deep breath before opening the door.

Gary was sitting at a small table in the corner. The line had died down and I ordered a small hot tea. I went over my mental list one last time as I walked to the table where he sat. "So where are you originally from, Gary ?" I asked as I sat down.

"Ohio" he responded.

"I'm from the midwest also!" I said excitedly.

"Oh" He responded as he sat and looked down at his coffee.

"So what did you move to this area for?" I continued, determined to get an actual conversation started.

"For my job." He pursed his lips together and bobbed his head.

It went on like this for 15 minutes. I quickly moved through pity to frustration. Did he understand how hard and awkward this was for me? While I had intended to make this as comfortable as humanly possible, I was slowly hoisting up my white flag.

So I sat. I stared at him. I waited.

What felt like the longest five minutes of my life passed in silence.

Mr. Socially Awkward sat across from me, clutching his coffee, staring at the chair next to him. He had made no attempt to utter a single word during my Gandhi-like protest. I wondered if 20 minutes was the shortest first date in all of history.

"Well Gary, It was great to meet you. I've got to get going now." I said as I stood up. He smiled at me and thanked me for coming to meet him as he stretched his hand out in my direction. I shook his hand and smiled, warmly.

I walked back to my car and sighed, this time in relief. I started laughing to myself out loud. It occurred to me in that moment that while Dad was indeed the ultimate bachelor, he was also notoriously a glutton for punishment.

Chad

Chad seemed to be more physically my "type" than any other dates I had bravely ventured on thus far. After being disappointed by the men that were luring me in solely with their wit and charm, I thought I should give pure physical attraction a shot. After all, who needs dazzling conversation when your eyes are busy admiring the fantastic workmanship of a guy like Chad?

I pulled up some of his profile pictures on my phone as I grabbed drinks with Evelyn and Napa. "What do you think of this one?" I asked my consultants. I flashed them picture after picture of him at the beach, shirtless and tan.

"Whoa!" Napa responded with an appropriately animated eyebrow lift.

"Seriously?" Evelyn gasped, as she grabbed my phone from me.

"I know, right?" I responded, smugly.

"But what about that picture of him drinking a beer off of a garbage can? Don't you think he looks..."

"Ripped? Look at his biceps in that picture!" Napa interrupted.

"I was going to say immature." I responded with a smirk.

"You never know what someone is like just based on their pictures, L.A." Napa reminded me. She was always good about roping me back in when I had the tendency to write someone's life story based on a trivial observation. I once had determined that a man smiling at me from across a bar was racist simply because his belt buckle was a certian diameter.

"I say at least go meet him for a drink. You have nothing to lose!" Evelyn urged. "Besides, look at that cute picture of his dog! He seems sensitive too."

Having been on a series of difficult dates in the last few months, I was starting to feel like I had nothing left to lose. I had learned to keep it brief, by just meeting up for drinks rather than lunch or dinner. Furthermore, I always made sure to communicate upfront that I had an obligation later in the evening so that I had a flawless escape plan. After the encouragement from Napa and Evelyn, I confirmed a date with Mr. Studly.

Maybe it was the lack of pre-date conversation, or maybe it was the blind date practice I now had under my belt, but I walked in to the restaurant completley confidant. I sat down at a pub-height table (the kind that was not easily mistaken for a "let's have dinner" table) and waited for Chad to arrive. "Three minutes late" I noted.

I watched as Chad entered the restaurant. I think you can observe important characteristics about a person just by how he or she enters a room. For example, are his eyes glued the floor? Is he warmly smiling? Is he fervently texting? Is he nervously scanning the room to find me? In Chad's case, he was floating into the room, not quite smiling and not quite focused on anything. This first impression would, in time, fit Chad like a glove.

I waved my arm high enough to catch his eye and smiled warmly at him. As he made his way over to my "just drinks" table, I stood up to greet him. We hugged hello and he mumbled something about not having been to this restaurant in a while and giggled, nervously.

Nate, the server whom I had befriended months ago, had seen me on numerous first dates and came over on cue to take our drink order. I ordered a glass of wine and Chad shockingly got the beer special. Nate gave me a quick glance that I instinctively knew was his way of letting me know he would come chat with us if I needed to be saved from first date hell.

Luckily, I was in an outgoing mood. I told him all about my line of work and recounted the most entertaining stories I could remember. I had him laughing in no time. Chad had very sweet eyes. There was a child-like innocence in them as they would grow big at the climax of my stories, and then narrow as he began to chuckle.

It wasn't long before I grew tired of talking about myself. Chad had barely said anything all evening. "So you have a Master's degree in geology, but you work in IT?" I prodded.

"Yeah, totally random, I know." He responded.

I waited for some sort of explanation or follow-up. Nothing. He sipped the remainder of his beer and flagged down Nate for another one. Then his eyes fell back on my face, expectantly. It became clear that I was responsible for the entertainment portion of the evening.

"Have you done anything fun lately?" I was confidant that this was a simple enough question to elicit a mutual conversation.

"Yeah! I totally built some corn hole boards last weekend with a buddy of mine! They are pretty sweet if I do say so myself. Wanna see some pictures?"

If you are unsure of my definition of a "beer guy", please refer to my post on Derek which describes my stereotype. "Wow that is so amazing!" I doted. "I can't believe that you made those all by yourself!"

What was I doing? It was as if I began dumbing myself down to connect with this guy. Was I twirling my hair on my finger and chomping on bubble gum as well?

"So tell me how you would go about making something like that? I'm sure it is not as easy as it looks! I would guess that you would use plywood and a router, but what do I know?" I flirted.

"Actually, that is exactly how I did it!" He lit up.

"Wow!" I responded as I smiled and most likely fluttered my eyelashes excessively. At this point, I had fallen down the rabbit hole and could not find my way back to intellectual reality. I hadn't ever played this role on a date before, and something about it became addictive.

"What other things are you good at, Chad?" I asked.

I could feel myself snuffing my little feminist "Jiminy Cricket" conscience inside to play this game. "Shhh little cricket conscience....it will all be over soon, I promise!"

"Well, I'm pretty good at pool!" He said with a big grin.

"Really? I'm terrible at pool! Maybe you could teach me?" I said as we both gazed over at the pool table just feet away. I'm sure a little part of me died inside as I took my act a step further. My mom surely taught me better than this. At least we wouldn't have to pretend to have conversations anymore. Besides, how could I complain about having Chad closer as he taught me the proper way to hold a cue stick?

"So why doesn't the white ball have a number on it?" I joked. Anyone who knows me is aware that I can only, at maximum, allow three minutes to pass before I crack some sort of joke.

"Well that is the cue ball. You use that ball to hit the other balls into the pockets" Chad helpfully responded.

I decided it was easier to continue playing dumb than to make him feel like a moron for missing my joke.

After two games of pool and three hours of playing a ditz, I was ready to call it a night. Chad was smitten with this character I had developed, and I was starting to feel guilty as my conscience persistently chirped at me.

As he walked me to my car I wondered how many men out there really prefer women to be so oblivious. I could see the appeal of an easy, relaxing night. After all, Chad was nothing but easy to be around. I understood why he seemed to float in to rooms, he didn't allow anything to weigh him down. There were no threats of challenging conversations or differing opinions with Chad.

I decided that I would be terrible at keeping up with my ditzy charade. It wouldn't be long before I slipped up and spurted out something about upper class white male privilege being the crux of the problems in America. Mr. Studly, or Mr. Simple as I had renamed him, was not going to be my perfect match.

Just as I was about to toss my hat in the ring, Mr. Simple pulled me in tight for the kiss of a lifetime. In that moment, time stood still, I got the butterflies, and my knees went weak. Every cliche phrase fit what I was feeling. I opened my eyes in a haze as Chad kissed me softly on the cheek and told me to drive safe. He walked away, studly as ever.

"Shut up, cricket" I whispered.

"What was that?" Chad said turning around.

"You drive safe, too!" I replied.

Jason

The beauty of on-line dating is that a girl like me has the ability to try on different types of people that I normally would not meet in my daily patterns of life. I guess I would say that it has the same appeal of on-line shopping. You might find 1,000 styles of name brand shoes at the local shoe warehouse. Some of them trendy, some of them classic, others are just clearly not your style. And who can pass up glancing in the back at the bargain room? The appeal of such an establishment is that both my 93 year old grandmother and my 7 year old cousin could both walk away with their perfect shoe match from the very same store. It is a reliable way to purchase good, comfortable foot apparel.

When you open up your shoe search to the wold wide web, your options are endless. All of the sudden millions of colors and styles are at your finger tips. The amateur virtual shopper may find herself overwhelmed with the sheer diversity of choices. The exotic designs far surpass even the most bold options in a warehouse. They are just waiting for you to consider them for that perfect place in your humble closet. The only downfall: you can't try them on before inviting them home. Is the appeal of exotic style worth more than the familiar comfort of trying a shoe on in person?

Jason was my proverbial on-line exotic shoe purchase. His foreign accent made me giddy when he would call. We spent hours talking about life, work, and how to be happy spiritually in the midst of religious burden. He worked hard, drove a nice car, and understood social justice issues in our American culture. Furthermore, he was not intimidated when I broached controversial topics. In fact, I suspect he thought I was sexier for doing so. Had I found a man that was the "whole package" with an irresistible accent to boot? Jason would send me bubbly text messages throughout the day to see how I was, and to spread his positivity in my life. It wasn't too long before I deemed him Mr. Open Minded.

Napa and Evelyn were beyond annoyed with my incessant rants about Jason. I took any opportunity to squeeze his name in to the conversation.

"Speaking of frozen yogurt, did you know Jason is playing like 4 sports right now? He stays so busy! He should reward himself with some fro yo every now and then."

They would politely nod their heads in a "That fact is just as interesting as the first five times you told us" kind of way. Evelyn, being the natural sweetheart that she is, would often ask me some sort of follow-up question allowing me to indulge in my latest obsession.

The first date day finally came. Jason scored even more points when he suggested both a time and a location to meet. One would be surprised at how difficult it is to get a man to take such initiative now a days. Maybe that is a broad generalization, but my "research" shows that the on-line dating kind of guy most often struggles with this type of assertiveness.

Armed with my trusty Spanx and a flattering shade of ruby lip gloss, I made my way toward the restaurant we agreed to meet at. Even I was checking myself out. This guy didn't stand a chance. I walked toward him as he stood on a corner waiting. Something about the thickness of the summer air after the recent rain made the moment feel romantic.

As I got closer, I grimaced at the "dad jeans" he was wearing. The romantic moment abruptly faded. Heck, even my dad doesn't wear "dad jeans." Mom keeps him relatively up to date. Reminding myself that inner beauty was much more important to me than outward appearance, I trudged on. Besides, a woman can always influence the fashion faux pas of a man she truly loves, right?

Jason was just as warm and bubbly in person as he was on the phone. There was an instant comfort that I felt in his presence. As we walked to the restaurant, he filled the silence with his bubbly humor. I felt a certain ease around him, as if we had been friends for years.

As we continued talking over a late lunch and several drinks, I had mixed emotions about how the afternoon was unfolding. Jason was still incredibly energetic and bubbly....maybe a touch too bubbly. There were no lulls in the conversation as we sat and talked for four hours. Throughout the course of the date, he was already holding my hand right on top of the table, like a seasoned couple would do. "Should we go somewhere new?" He interrupted my thoughtful analysis. I was completely caught off guard.

"Somewhere new?" I thought. "We have been on our first date for four hours already!" My cheeks were throbbing from the courtesy smiles I had been giving to indicate the important social cue of being engaged. I was beginning to think that Jason was like a super cute strappy sandal: designed to flatter your foot while simultaneously giving you the worst blisters you have ever had.

Upon arrival to our new restaurant, I promptly texted Napa and Evelyn. "If you love me like you say you do, you will get your butts down here". Like any best friends would do, they were instantly on their way.

"My friends actually were in the neighborhood and they are going to stop by. I hope that is OK with you" I fibbed.

"That would be great" Jason gushed. He immediately grabbed my hand again when I sat down. It was if he was excited to move on to the "meeting the friends" portion of our five hour relationship. Little did he know I was sending in the artillery.

Napa and Evelyn arrived in no time, and we all decided to order dinner. That's right....I was now having a second meal with my lunch date. Jason continued holding my hand in plain sight, slowly stroking my thumb with his index finger. I blushed with embarrassment, as I knew I would get an earful from the girls later on. I was beginning to grow concerned that he perhaps brought a engagement ring along with him.

Napa has been known to boldly save me from awkward situations with men in the past, and this date was no different. She immediately relieved the pressure by asking Jason many questions about himself. I finally was able to breathe as the spotlight moved from me to him. Evelyn was a strategic invite as well. She calmly engaged me in conversation while Napa did her thing. I even found an opportunity to naturally disengage my hand from the death love grip of my potential suitor.

The moment Napa went to the restroom, Jason leaned over and whispered "I am going to nickname her the Spanish Inquisition". He giggled, clearly amused at himself.

"Yeah, isn't she just fabulous?" I said with a grin.

Ten o'clock finally rolled around. Had this date really lasted 9 hours? How could I have let that happen? The girls were perceptive of my exhaustion and wrapped things up for me. As we all walked out of the restaurant and said our goodbyes, there it was again: the death love grip. He walked me to my car, which happened to be in the opposite direction of my beloved Napa and Evelyn.

The moment was upon us. The awkward first date goodbye. As I went in for a friendly hug, Jason suddenly mauled me with a very open-mouthed kiss goodnight. "Is it over yet??" was the first thing running through my mind. Most often, it can be considered a bad sign if one recipient of a kiss is waiting in anticipation for it to end. It wasn't over yet. "If only he could close his mouth just a little bit...it wouldn't be so bad" I analyzed as I waited.

As soon as he released my prisoner lips, he thanked me for a great evening. I watched as he and his "dad jeans" walked away to his car. In that moment, I was certain that Mr. Open Minded was truly Mr. Overeager.