The DC area can be a tricky place when you’re single.

For starters, it’s a workaholics’ dream come true, especially if power, money or good old fashioned “palace intrigue” are someone’s raison d’etre. That makes for very busy types who spend far more than the minimum forty-hour work week focused on their professional careers, deals and social ladder climbing maneuvering and power games. The DC area caters to big ambitions and even bigger egos, where the unofficial bravado or mating call is “DO YOU KNOW WHO I AM?” Being an already over-populated area that invites more and more people to move into the area, while many will spend as much as two hours one way commuting to their jobs, if happy hour isn’t less than an hour away, then it isn’t worth the drive.

The net result is it makes for a somewhat anti-social environment. Drivers participate in the quasi-gladiatorial “survival of the fittest” experience that includes cutting each other off; racing or weaving their BMW, Porsche, Mercedes or Maserati mid-life-crisis and/or look-what-I-got-bitches status symbols through congested traffic; and people adopt hard-to-get-membership-into urban cliques and neighbors barely speak to each other to the point of not even knowing their names even after years of living next door to each other.

This can make for a precarious landscape to navigate around in for the average single person, especially in the dating scene and if you’re of the introvert or socially-awkward variety. In addition to the “friends are marrying and having kids” and “romantic comedy” fueled pressure placed on the average single person, being a veteran of the nerd/geek/alternative crowd outcast of teenage social strata only adds to the challenges of meeting new people. This can include brainy nerds, sci fi/fantasy fanboys, struggling artists and the otherwise shunned-by-the-in-crowd wandering souls.

Being a member of this group, I own the fact that meeting new people as friends, dates or just to build up my social circles can be an uphill battle at times. It also means that I draw in similar types. I can count how many tense first dates I’ve had with women whose conversation styles strained against the lack of chemistry, endured awkward silences, or anxiety-saturated nerves leaving them shaking at the table. The old joke goes, How do porcupines mate? Very carefully. and those in this crowd aren’t much different thanks to their over reactive defense behaviors. This amounts to far too many nights alone eating in the living room in front of the TV or being the third or fifth wheel when out with friends and their significant others. It also means that rather than cruise bars or dive into crowd-drawing events that are Hell on Earth for my types, other avenues are relied on for meeting someone special.

And now, a confession…

Like many, I’ve used the mainstream online personal sites (e.g., Match, POF, OKCupid, etc.) to push forward my love life, but this includes rolling the dice on the “anything is possible” world of Craigslist. To date, I’ve known of or met several couples who met, dated and even married each other because one of them posted a legitimate “seeking a relationship” ad on a website better known on the Internet as “Big Lots has a Garage Sale,” “Costco for Prostitutes” and/or “I Want My Vital Organs Stolen.” The quasi-anonymous and free-of-charge nature of the site sometimes means you’re probably going to meet some of the more fringe-occupying members of society. And of the few people I engaged in extended email and phone conversations and even fewer who I met in-person, there is a bit of
truth to this notion (not to mention the rampant catfishing found on there). Nevertheless, I argue that you’re just as likely to meet a would-be axe murderer in any bar as you might through a personal ad.

I’m pretty sure that of the many people I met thanks to online dating, the more socially odd and/or morally questionable were met via Craigslist. Some examples who come to mind include one woman who described herself as “petite,” but was so anorexic that she could barely manage walking a few blocks from the parking garage to the restaurant, and was so rude to our waitress that I added a 100% tip to compensate (I also hoped and prayed she didn’t do anything to our food). Another turned out to be an attractive woman who lied about her age, got herself drunk with me, and admitted that she was thinking about filing for divorce and I was the third man who she had considered cheating with. And then there was my last Craigslist encounter with a woman who was so nervous or out of it that she barely spoke over dinner and dressed so frumpy that I almost wondered if she was homeless. This isn’t to say all of the Craigslist dates were bad experiences. On the flip side, I met one woman who I dated for several months before life, the universe and everything nudged us onto diverging paths in life.

And then there was the case of “Jennifer” (not her real name).

When Craigslist still had its personals section (no gone because of the Fight Online Sex Trafficking Act, which is well-intended, but killed off the personal ads on there), it wasn’t unusual to see the same ads reposted or users posting similarly-written ads. These serial posters became almost familiar and easy to spot, especially as some used the same pictures in their ads. Jennifer was one of these types of Craigslist regulars (and no, I was not one of those types – I made it a point to never post more than once a month). Despite my seemingly ignored response to one of her posts just a few weeks earlier, I was pleasantly surprised to see her respond to the one I posted (I knew it was her because she attached her often-posted pictures to her email).

I replied with a friendly and open-ended email, making some kind of mild joke that I had contacted her through her ad and thought it amusing that she answered mine anyway. This led to an understandably awkward email “Oh, uhm…how funny! I guess I [PLACE YOUR FLIMSY EXCUSE HERE] and didn’t get to respond to you” email exchange. After a few rounds of emails, I expected that to be the most I’d get out of the conversation, and elected to move on to other things. Surprisingly, Jennifer emailed me a few hours later, asking some of the usual get-to-know-you ice breaker questions. Over the next few days, she and I traded more pictures, funny stories and tidbits about our lives to encourage my interest. There were a few missteps, such as my insistence on generally not dating anyone living across the Potomac (I found fighting traffic, even on weekends, to be way too much of a pain in the ass), and hers that she wasn’t sure about having children (which I did, but I pointed out that the prospect was something way down the road). Still, interest was there and between a few of her pics proving that she didn’t mind showing a little cleavage, and some flirty risqué banter from time to time.

One fact of the online ads is you tend to operate in a vacuum about certain things. Whereas at a bar or party you have the advantage of seeing and experiencing a person right there and then to know if there’s attraction or interest, doing the online routine meant either working with very little “real world data” or accepting whatever they share with you as valid. This is awkward enough while compounding your own socially awkwardness. Also, if you’re hooked on certain qualities – physical attraction (e.g., must be tall or athletic) or certain psychological requirements (e.g., must not have ever been in an “institution”), then interested parties can sometimes engender misleading assumptions about one another (a broad spectrum of everything from outright lying about one’s self, to stretching the truth, to open-for-debate self image). Another aspect of this is while some people feel that true connections can be made through a computer screen or wifi signal, the experience of meeting someone in real life can often be far different than the online personae we’re attracted to.

My rule of thumb is to never meet someone without at least one phone conversation prior to meeting. This helps establish that the person is real and gives an idea of who they are in real life as opposed to impersonal emails or IMs. After agreeing to meet for drinks that coming weekend, Jennifer and I spoke on the phone, but seemed to take a few nights to coordinate the when and how. She sounded a bit nervous and unsure of herself, but was laughing at the right times and didn’t give me any mental “red flags” for me to call off the date. She was far less flirty and suggestive than some of her online conversations, but meeting someone new sometimes means keeping things as neutral while “breaking the ice.”

That Saturday, I was at the corner of a nearly-empty bar in Fairfax near the Fair Oaks Mall. I arrived early mainly to get out of the house and fight through an unusually chilly and rainy Spring evening. My cell phone pinged from time to time, a mix of “hey, how’s it going?” texts from friends who knew I was out on a date, and Jennifer letting me know that she was on her way or delayed due to traffic. In the meantime, I sipped water and people watched. I was amused by what had to be another first date couple – a woman who was teetotaling her martini and leaning furtherer away from a man who was gulping down Scotch and getting grabbier with each swig. A few others were making the most of the early-Spring lack of interesting sports on TV. This was not the place to go on the hunt for fresh meat in the singles market, but was good for having a conversation without screaming at each other.

Jennifer finally arrived about twenty minutes late, texting me while in the parking lot that she had arrived. I already told her that I was at the corner of the bar and what I was wearing so she couldn’t miss me. I saw her walk in and was relieved that she did, in fact, look like her picture. She said that her father is white and mother Korean, and she unmistakably favored her mother’s side. Jennifer had long and flaxen jet-black hair, short, and a curvy figure. She wore an open trench cost showing a plain white blouse that was unbuttoned just low enough to pleasantly reveal cleavage for her breasts, and black jeans that gave away her perfectly wide hips. Imagine Mia Lelani if she gained about 10 pounds in all the right places. She had dark brown eyes and a wide smile, but seemed a little anxious as she walked up, cell phone still in hand. She hurried over to me and sat down, still wearing her coat.

Picking up that she was a little nervous, I tried helping her settle down with innocuous conversation – How was your day? DC traffic – amIright? The bartender, who wasn’t over run with patrons, quickly mixed her a mojito that seemed almost in sync with my attempts to get her to relax.

She was still a little tense, but was at least carrying on the conversation in a natural cadence and energy. She was frazzled from the heavy rain making driving over a chore and was a little wiped out. Jennifer’s day job was as an office manager during the week, and then helping out at her parents’ convenience store in Arlington on the weekends. She usually had Sundays off, but hadn’t in over a month, and was tired of working seven days a week. She didn’t take her coat off the entire time claiming that she was chilled (it was a little cold in the bar), but pulled it back enough to sit comfortably on her barstool and show off her outfit. I was catching myself staring a bit took much at her bust – her blouse kept opening up to show off even more cleavage to the point that I could see the edge of her black lace bra.

As time went on and more mojitos were served, Jennifer seemed to relax and was even showing sparks of the flirty, suggestive woman I traded emails with. The conversation still felt stilted, uncomfortable and our jokes didn’t always seem to hit their beats at the right moment, but the subjects kept on coming. She had a healthy laugh and eyes that smiled with it. Her every curve beautifully shook with laughter. She kept her hands to herself, but made far more eye contact with me than when she first sat down.

By the time we wrapped up the evening, only a few stragglers remained and the rain had finally ended. We stepped out of the restaurant with a bit of a hesitant stop – were we saying goodbye there or at the car? I moved forward and she followed a half step later as we awkwardly talked about other inane small talk to fill up the time walking into the parking lot. As we stood by her car, offering each other the “this was nice, I want to see you again” send off, we couldn’t seem to figure out if we were ending things with a handshake (i.e., a bad sign in my book) or a hug (i.e., much more promising). She went in for the hug, that was a full-bodies pressed against each other wrap that I admit I was enjoying a bit too much given her attractive figure. As we began pulling apart, we made eye contact for what must’ve been a fraction of a second. In that moment, I saw a flash of desire, some primal spark that said “WANT.” And with that, she grabbed me closer and slid her tongue deep into my mouth. Her arms were tight around me and her body pressed hard as if any space between us was too much for her. Her tongue wrapped about mine, exploring and tasting each other. My hands stroked her back – feeling the back strap of her bra was arousing just by itself.

We finally separated, and she quickly jumped in her car telling that she’d text or call tomorrow.

Another dating best practice I’ve learned is to not badger someone after a first date. Let them know you’re still interested, and give them time to respond in kind. Email bombing, leaving lots of voicemails or death by text message is a sure fire way of irritating or creeping someone out and ensuring they never contact you again. I’ve never been the needy or jealous type, so mixing patience mixed with a healthy amount of self-control has served me well in the past. Nevertheless, by Tuesday afternoon, I was beginning to wonder if she had even read my text on Sunday the told her I looked forward to seeing her again. Wednesday night, as I crawled up the stairs of my condo building and collapsed into my home after a tougher-than-usual gym workout, my phone rang.

Jennifer apologized for being so quiet. The long-story-made-short is that was still living with her parents, and they were the “a bit on the old fashioned” side of how she should date. This was even to the point that she sometimes felt as if her every move was watched at home, and she was incredibly self-conscious while texting me while at home. This made a little sense to me since I noticed our previous email exchanges were during the day – which I guessed was while she was at work. This particular night, her parents were both at their store, so she was free to talk. As luck would have it, the following weekend was looking good for meeting up since she finally had a Sunday off and convinced her parents that she was staying at a friend’s place that night. I assumed that meant meeting sometime during the day, and started listing possible date ideas, but she cut me off. She was thinking more like watching movies at my place Saturday night. I immediately agreed, picked a good time for her to show up, and I gave her my address.

After spending the next few nights cleaning the Hell out of my condo and shopping Saturday morning to take of a list of “must have” food, drink and amenities for that Saturday evening, I was awaiting her arrival. I received a few texts from her throughout the day, asking if she needed to bring anything and confirming when she was leaving the store. She arrived about an hour late, but that wasn’t a big deal considering I was at home. She called from the parking lot to make sure she wouldn’t be towed in the spot she picked, and moments later knocked on my door. She was wearing nearly the same outfit from our first date, though I’d swear her blouse was tighter and more sheer than the other. This time, she took off her coat.

Although I managed to cobble together some appetizer type fare that was easy to warm up, she walked in with a plastic bag smelling of wonderful food – all Asian and delicious. As we ate and talked, we shared a bottle of wine and tested each other’s trivia knowledge of the songs playing through my cable’s music channels. She still seemed a bit on edge and I made some humorous comment to relax.

She smiled and responded with “Sure, maybe after a shot or two.”

I pointed to the small bar I kept in the dining room with a few bottles to choose from. Jennifer immediate snatched up the tequila and asked if I had any limes (I did). We each took a shot and joked about who could hold their liquor better. I gave her a quick tour of the condo and we had another shot. Went back to the living room, still testing each other on music trivia and took shots for each right answer.

Sitting on the couch, she was much more relaxed, leaning on the cushions, her blouse opening enough for one of her breasts to slide out a little. This time, it was a purple laced bra. The conversation was more flowing now, and was starting to get peppered with more flirty and suggestive comments and inuendoes like we were online. Occasionally we touched hands, but my instincts told me that it wasn’t time to slide closer. Her body language still seem a little tense and not quite comfortable with anything more. I watched Jennifer as she stood up and wobbled a little making her way to the bathroom and back. She stood next to me and offered a hand. I took it, she helped me up and said it was time for another shot.

At this point, the wine and tequila were taking their toll on me, and I was having trouble walking straight myself. We managed to wind our way into the kitchen. We poured two more shots and downed them. Still standing there, she leaned against me and wrapped her arm around my waist.

“Shit,” she laughed, “I think I’ve had enough!”

Jennifer looked up at me, and smiled so much that her eyes closed but paused as if frozen and unwilling to move more. “I’m glad I came here tonight.” It felt as if she were trying to straighten up to get closer, but then nearly slipped on the hardwood floor. I caught her as we both laughed at her yelp. I helped her stand up straight after a couple of tries, then she clumsily reached for my head and pulled me in for a long kiss.

“Let’s go sit back down,” I said, “Before we get hurt!”

We stumbled back to the couch where I tried to maneuver her into a better position to sit down. She seemed either unable to move or wasn’t sure what I was doing, so the manipulating us around was a bit of a workout. One of my legs ended up semi-twisted up with hers and we collapsed onto the couch with her landing into my lap on top of me. Again, more laughing – we were drunk.

Jennifer laid on top of me for a moment, almost as if she needed to decide something, then casually turned her head to face mine and we started kissing. Just like our first date, our tongues danced around each other – feeling everything. She reached up with one arm to hold my head while putting her other hand on top of mine resting on her stomach. My free hand rested on her thigh and my cock hardened as her ass rested against my crotch. She had pulled her hair back into a ponytail, leaving it easy for me to kiss her on the neck or trace her ear with my tongue. She half-moaned as I slid the tip of my tongue into her ear and then down her neck. Jennifer withdrew her one hand from my head and onto my waist.

As I was necking her, I began sliding my one hand from her stomach up to her breast (her hand still on mine). Her breathing quickened and deepened as I cupped it and my fingers brushed the edge of her bra. She had perfect breasts. Large and heavy, far more than the “more than a handful” size but just enough for exploring. I slid my other hand up her thigh until I almost touched her hand, and she moved it away and began unbuttoning her blouse.

I kissed my way back to her mouth and we deep kissed for who knows how long. I could feel her nipple hardening through her bra and blouse, and she was feeling her other breast with her own hand. As I kissed by her ear, she moaned ever so gently.

“What…” she barely whispered. “What are you doing to me?”

“I’m trying to turn you on,” I whispered into her ear.

“Why?”

“Because…I want to fuck you.”

She moaned louder. “Get these clothes off and fuck me.”

Admittedly, in our inebriated state, it was an exercise in contortion and weight lifting to get us both off of the couch. My hands now on her waist, I directed her from behind down the hall and into the bedroom. At the foot of the bed, she turned around and kissed me. She had managed to unbutton and untuck her blouse. As we kissed I pulled off my shirt and felt her breasts press against me. She reached down and rubbed my crotch, feeling my cock getting harder and longer as she felt it.

With a gentle push, she fell backward onto my bed and began undoing her pants as I crawled on top of her, nuzzling her neck and kissing down to her breasts. I held them both with my hands as I kissed them all over, then traced their curves with the tip of my tongue. She was pushing her pants off as I unclasped her bra, pulled it off with her blouse and began sucking and flicking her nipples with my tongue. I felt her half kicking to get her pants off and she reached down to my jeans to unzip them and reach inside.

I moved down, kissing along her stomach while pulling off my jeans. Still holding her breasts in my hands, I kissed along her panties as she spread her legs in obvious want. She took over playing with her breasts as I reached down and pulled her panties off, revealing a totally smooth and definitely wet pussy. I teasingly kissed down to her clit, then veered up her inner thigh just to hear her slightly disappointed and eager moan. I pushed her legs apart more and dove in. I spread her lips apart with my tongue in a broad pass where she gasped if definitely surprise and pleasure, then traced back around her lips. I took turns playing with her clit and flicking inside her pussy while I took turns feeling her breasts and then her ass, enjoying every sound coming out of her.

I eventually made my way back up, tending to breasts with my mouth and then back to kissing her. Jennifer yanked down my briefs and grabbed my cock with one hand, half gipping and half stroking it. She began pulling it down between her legs and I stopped her as she groaned in frustration.

“Wait a moment,” I said.

I reached over to my night stand and got out a condom and quickly put it on. Jennifer smiled.

As I got back on top, her legs spread apart for me to enter her. I felt how wet she was even through the protection and then the pleasant crush of her pelvic floor muscles – either she’s very gifted or does her Kegel exercises. I moved slowly at first, enjoying the feel of me inside her. I was laying on top, feeling her magnificent breasts heaving back and forth with me. Jennifer kissed me and licked around my lips and I could still taste the tequila on hers. Soon we were pounding back and forth, the bed shaking from my hips ramming into her and her moans getting deeper and louder. At times I’d lift myself off of her and kiss and suck on her breasts, or she’d grab them herself to play with.

I could hear in her voice that what I was doing worked for her. Her groans became gasps. Her gasps became yelps and shouts. Then I stopped, pulled out (accompanied by her groan of disappointment), and turned her over onto her stomach. Grabbing her hips, I slid inside of her from behind and began to pound my hips into her ass. I slipped my hands in front and grabbed her breasts, clutching them and feeling them as hungrily as before. She raised herself off the bed to be in front of me on her knees so she could turn her head to kiss me. Our tongues playing in-and-out games like my hard cock inside her.

After more than a few position changes, we slowed down and I pulled out for a short break. I spooned her from behind, my warm, wet cock resting right down the middle of her ass, my arm draped over her as I nuzzled and kissed the back of her neck. I almost wondered if Jennifer fell asleep on me, so I rubbed one her breasts and gently pinched her nipple until a pleased moan told me she was very much awake. I already pulled the used condom off, and she laid one arm on my hip. Her hand slid down to my still hard cock and she slowly felt it. First, it was a gentle gliding touch of her fingertips, then her fingers wrapping around it to stroke it. Her hand was warm and my cock grew even harder.

She was getting me back into the mood of entering her again, so I stood up on my knees and reached to my nightstand for a fresh condom. Jennifer stopped me in mid-reach, rising up by almost climbing my legs with her hands. Her head was next to my cock, still stroking it as she used the other hand to hang onto my hips. Then Jennifer began tracing my cock with her tongue, first around the head then up and down its shaft, nearly wrapping her tongue around the base, then back up to the tip. She kissed the tip of it, then slid it into her mouth, this time getting a moan out of me as her wonderful mouth took me in. Hanging off of me, so eagerly sucked on it back and forth, and I put my hand on the back of her head.

I gently prodded her to lay back down on the bed and shifted around so she was still sucking my cock as I climbed on top and put my head back between her legs to lap at her wet pussy. Eventually I laid on my side, still eagerly eating her out as she addressed my hard cock. Jennifer got up, pulled a fresh condom out, put it on me and threw a leg over my hips to lower herself onto me. She bounced up and down, hiding my cock with even more zeal than before. I tried rubbing her clit but couldn’t get an opening as she worked on top of me, so I took turns either grabbing hard onto her hips or breasts. She yelped with every bounce while all I could feel was her warm, wet pussy smothering my cock deep inside of her. I sat up and licked and sucked on her bouncing breasts.

Soon enough we slowed down and laid down with me behind her again. Despite everything we did, I was still hard as a rock and wanting more of her. After donning yet another fresh condom, I moved my hips down to her ass, and slid into her pussy while we laid on the bed together. Maybe it was how late it was and all of the night catching up with us, but this time I was more gentle and rhythmic as I moved back and forth. Jennifer turned her head again for some light kissing and rubbed her clit. Before long I felt even more turned on than before, quickening my pace until I could feel my cock ready to explode. I plunged my tongue into her mouth as I felt my cock stiffen and I locked my hips against her, my cock pumping hard as I came inside of her.

After that, we settled in for the night, pulling the covers up and falling asleep in each other’s arms. In the morning, we made more small talk over coffee. Jennifer took her time getting cleaned up and even asked to borrow a t-shirt (her blouse was showing signs of last night). She had errands to run and I took the hint that she wanted to take off, and let her.

As the weeks and next few months went by, we managed to date on and off as her schedule allowed, but it was clear that living at home with her parents was definitely cramping her style. I suspect her father was getting suspicious of what she was up to, and soon enough Jennifer was back to working every weekend at the family store, pretty much cutting us off from any regular get togethers and dates. Labor Day weekend, it was clear that we weren’t going to be able to have a substantial relationship until she managed to get into her own place, and eventually we parted ways.