Lawyer Boy

My dating world is too small yet again — Part II

August 2004

What are the odds that I would run into Lawyer Boy after a year when I'm out on a first date with another guy? DC is a small town, but my world is especially small.

I stared at Lawyer Boy for a few seconds. He saw me at exactly the same time that I noticed him. We smiled at each other, and he extended out his hand to help me up the last step toward him.

Lawyer Boy and I hugged and just started talking to each other like no time had passed since our last date. I then turned and saw Justin, our mutual friend, and Char, the girl who told me that Lawyer Boy was living with Darby. As I kept talking with everyone, I looked down the bar for my date, Calvin. I waved at him, smiled, and gave him the sign for "one minute."

"I'm actually on a first date with this really nice guy. I shouldn't keep him waiting too long, but it's great to see you guys," I told Lawyer Boy and Justin.

Justin joked, "The three of us should hook up one night with me in the back and Lawyer Boy in the front." (That comment might seem offensive or out-of-left-field, but I didn't take it that way. Justin is as much of a flirt as I am.)

We all laughed out loud, as I replied, "Well, if we were doing that, then Lawyer Boy would have to be in the back. And, Justin, it might not be wise to talk about threesomes that don't involve your girlfriend when she's standing five feet away."

Justin chuckled, and Lawyer Boy's face was beet-red.

"So, are you guys going to be here long?" I inquired.

"Yeah, probably," Justin responded.

"Well, let me know if you decide to head somewhere else. I should go back and spend some more time with my date, but I hope that we can catch up more later," I commented.

I went back to Calvin on the other side of the bar. For the next hour, I tried to feign interest in the conversation, but it didn't work. Calvin was a good guy, but the moment that I saw Lawyer Boy, I knew that my first date with Calvin was going to be my last.

I kept looking over to see if Justin and Lawyer Boy were at the other end of the bar. Calvin didn't notice, but I realized that I should just be honest since neither my heart nor my head were in the date anymore.

"Hey," I said. "You seem really cool and it would be nice to grab coffee or catch a movie sometime. But, tonight, I wasn't expecting to run into my friends and I'd like to go grab a drink with them to celebrate my friend's birthday. I don't want to be rude, but would that be okay?"

"Of course! We can hang out another time. Go have fun with your friends," he replied.

I was pretty surprised that he took that so well. Calvin won a lot of points with me with his laid-back attitude, and I wondered if we could actually be friends. (Oh, I'd like to say that this was the only time that I ditched a guy on our first date for an ex-boyfriend, but it wasn't. I realize that I'm not always the perfect date!)

I gave Calvin a hug and a kiss on the cheek goodbye, and headed to the other side of the bar. I must have looked like a chicken with its head cut off because I couldn't see Lawyer Boy, Justin or Char anywhere. Finally, I walked to the top of the Waterfront complex and called Justin. He said that they were getting burgers at Johnny Rockets and that I should come up.

I walked up to M Street and inside the restaurant (yes, I'm being kind to Johnny Rockets by even calling it that). Char and her girlfriend had gone home so it was just Lawyer Boy, Justin and two other guys. We got on the topic of graduate school since I was starting a master's program in a week. It was fun to talk with them all, and there were a lot of laughs, as expected with that group.

I had already eaten so I just got a soda and had a few of Lawyer Boy's fries. When the bill came, I offered to pay my share, but Lawyer Boy said, "I'll take care of it."

"Thanks. That's sweet," I responded, as I put my hand on his leg. Putting my hand on someone's leg wasn't normally a big deal. I do that with my girlfriends as a sign of affection or appreciation. But, with Lawyer Boy, the act wasn't so casual. He flexed his quad the moment that I put my hand on his leg. I squeezed his leg to feel his muscles and made some comment about how he must still be going to the gym a lot. He was blushing by this point, and it seemed as though we were the only two people at the table. All of that transpired in less than 30 seconds, but I knew that we would have sex again. It wasn't a matter of if, but when.

We all said goodbye outside of Johnny Rockets. Justin crossed the street to head toward the parking garage, Lawyer Boy headed toward Wisconsin and his apartment, and their friends offered to walk me to my car. The night might have been over, but my intuition told me that the saga with Lawyer Boy wasn't.

My dating world is too small yet again

So, in May of 2003, I learned from a mutual friend that Lawyer Boy had a live-in girlfriend (Darby), and ended my relationship with him. I missed Lawyer Boy, but a significant other was a deal-breaker for me after I had worked so hard to leave my tumultuous affair with Married Matt.

Six weeks later, I reconnected with my ex-boyfriend, Basketball Boy. We were dating again, but it didn't feel as though we were as close as we had been before.

Basketball Boy's company had transferred him to Pennsylvania that November. He promised that he would be back down in DC on a regular basis, and he was. I saw him one or two nights a month, which was enough to keep me coming back for more. But, the timing of his move with our unsettled dating mode took our relationship to a new — and not necessarily good — level.

Basketball Boy and I talked on the phone and texted less. Once in a while, we would get in a sexting marathon, but those sessions weren't the norm. And, when he was coming down to DC, he had this knack for not giving me a heads up or making plans in advance. The result? My phone would ring at 1 in the morning (or 2…or 3), and Basketball Boy would be downstairs in the lobby of my building or asking me to meet him at a friend's house. I could have told him, "no," but I didn't. The sex was great, and I always loved spending time with him. I was like puddy in his hands.

Nonetheless, I knew that things had changed and our connection was different. Basketball Boy and I would go out on dates, but those dates were never lengthy affairs (breakfast, movie, quick dinner, etc.). And, some of his visits just consisted of a few hours of sex, a few hours of sleep and me driving him wherever he needed to go in the morning.

It was clear that work came first, coaching baseball and his best friends came in at second, and I was a distant third. What's that old saying? If it looks like a duck and it walks like a duck, then it is a duck? Well, our "dates" seemed liked booty calls and felt like booty calls so they must have been booty calls, right?

"This is starting to feel like I'm a booty call," I told Basketball Boy. "When you're coming to town next, would you mind letting me know as you are driving down? "

"You aren't a booty call. We've known each other forever. I always make time for you, but I can't stop working on the ride down to call you," he said.

"Well, then text me…or something. I love seeing you, but the 2am calls after you've been out drinking with your friends are getting old," I explained.

That pattern didn't change much, but by August of 2004, I had…a little. I wasn't sure if I was ready to date someone else, yet I knew that I wanted a more defined relationship. At that time, the dating website, eHarmony, was taking off and I fell prey to the company's great television marketing techniques. I set up a profile and began e-mail exchanges with a few guys.

I didn't feel pressured to find anyone or go out on dates so I waited until I found a guy with whom I thought I could connect. Calvin was black, Christian, athletic, optimistic and doing well in the tech field. After two weeks of e-mails, we decided to meet for drinks on the Georgetown Waterfront.

The weather was perfect, and the Waterfront is one of my favorite spots in DC. Calvin made me smile and laugh. Conversation was easy with him, and not surprisingly, we knew some of the same people in town. (I had met Calvin's business partner several years prior at The Palm, and he ended up designing the website for my first law firm.) After an hour or so of an enjoyable first date, I excused myself to the bathroom.

As I was walking inside, I wondered if I was ready to move on and date someone else. I also was trying to decide if height was a deal breaker for me. See, Calvin was 5'8", and I'm 5'9 1/2". I know that's not much, and I have dated shorter guys before, but it's not my preference.

I headed back outside from the 'loo and realized that I didn't have to figure that all out right then and there. This was just drinks and calamari. I wasn't marrying the guy, and he hadn't even moved in to hold my hand yet. Why over-think things?

I walked up the four steps from the patio to the bar level. Calvin saw me from the other end of the bar, and we smiled at each other. Then, I turned and found myself face-to-face with…

Lawyer Boy.

Lawyer Boy on my mind in 5-7-5


Trying to forget
Our affair. My memory
Like an elephant

Was doing so well
Put away the Kleenex box
With my old yearbooks

‘Til I saw the pic
Of Darby’s pregnant belly
Floodgates have opened

Oh, how I miss you!
The sex, the law, your friendship
Did I mention sex?

No! I don’t miss you!
Your lies, cheating and ego
Almost Clinton-esque

I’m the lucky one
(Deep down I know this is true.
Just keep repeating)

To not be your wife,
Expecting your baby and
Hoping you will change

When child is born
Will you really be faithful?
Doubtful. [Sigh.] Doubtful.

You’re a risk taker
One woman is not enough
Cheating — like your drug

Absence makes my heart
Confused. Like DC weather
When will seasons change?

*I think a lot in 5-7-5 syllables. When Lawyer Boy and I were dating before I knew a Darby even existed, I started sexting him with haikus. Earlier this evening, I was processing my feelings about his wife’s pregnancy and the above verses just came to me.

All the single (and proud of it) ladies…now put your hands up!

When I meet someone for the first time, I'm often asked, "Are you single, City Girl?"


I gaze into the person's eyes and notice his or her surprise and concern on my behalf. Any of the following questions might be uttered next:

"How old are you?"


"A girl like you? You're a catch!"

"Isn't your biological clock ticking?"

"Aww. The right guy is out there. You'll find him."

"You're not getting any younger. Don't you want to get married?"

If I actually answer the follow-up questions honestly, it would catch most people off-guard. Yes, I'm single, but I'm not necessarily looking to get married. It amazes me that in 2009, that's not a choice that garners as much respect as the other options out there.

My friend, Ash, and I got into a discussion about this recently. She and I are the same age, have made smart career choices, would be deemed "a catch" by conventional standards, and aren't sure if we see marriage in our future.

We weren't raised with marriage as the end goal or even a major life goal. We are both only children and value our independence. Our families emphasized our education and doing well in whatever profession we chose. We happily take trips, go to restaurants, and head to the movies on our own. We have an active social life with wonderful girlfriends. We don't go to sleep at night, feeling that our lives are incomplete because there's an empty pillow in the bed next to us.

"We don't need a man," Ash said, summing it up perfectly!

"And, a lot of the time, we don't even want one," I replied, as we both laughed.

I've admitted to being commitment-phobic in the past, but that's very different from where I am now. To provide some clarification, here's the back-story:

At 16, I broke up with my high school boyfriend, Boston Christian. My Mom thought that was a smart move, and told me that I shouldn't have a boyfriend in college. She also informed me that she didn't want me to bring any guy home unless we were getting engaged. (Keep in mind that this was coming from a woman who defied Irish-Catholic norms by focusing on her career and not getting married until she was 34 years old.)

The "no-boyfriend" mode worked for me since I viewed my family and girlfriends as the most important things in my life. School and work came in at the second tier. And, guys were "other" — for sex. Granted, I had a lot of sex so I won't devalue one of my favorite hobbies. But, it was just that to me… a hobby!

At around 25, shortly after my Mom died and my relationship with my Dad changed significantly, I entered a phase of being fearful of commitment. That lasted for quite a while, and I'm sure was a huge reason why I ended up in serious relationships with married men (Married Matt and Lawyer Boy) and fellow commitment-phobes (Basketball Boy).

Now, though, I'm in a new phase. I'm open to finding someone in my life to spend time with, but I realize that I LOVE my life as it is. I don't know that I want to share it with someone. The thought of coming home to the same person every night is just not that appealing to me. The only child in me craves her alone time, the Type A girl in me wants to keep my place immaculate, and the independent woman in me doesn't need help with her bills nor anyone to question how much time she spends with her girlfriends.

On the sex front, I used a line in college that "I like pizza, but I wouldn't want it everyday." There's a large part of me that still feels that way. Only sleeping with one person for the rest of my life? I might not perish the thought, but monogamy doesn't exactly have me jumping up and down.

Am I adverse to love or marriage? Not at all! I do have a sappy, Hallmark side to my personality. And, I respect the idea of marriage, but I'm not going to get married for the sake of it. If I can look into a guy's eyes and know that I'm going to be faithful to him forever, then yes, I'd consider getting married. But, the thought of "'til death do us part" seems like quite a stretch for me at a time when I don't really care to spend more than one or two nights a week with any guy.

And, since marriage and children are related subjects (pun intended), I'll address the question of kids. I see myself adopting one of the millions of children in the world who is in need of love, a home and a family. I don't need a man to do that biologically or financially.

In addition, when it comes to child-rearing, I worked as a nanny or babysitter during high school, college and law school. I have very definitive ideas about raising a child, and am disappointed at the fact that the majority of my girlfriends with children work outside of the home, yet are responsible for a disproportionate amount of the workload inside the home. I would much rather pay for a nanny who has experience with child care and will follow my instructions than have a man who is supposed to be my partner in parenting not doing his share.

I also have quite a few friends my age who don't care to have children…ever. Some are married, some are in relationships, and some are single. And, I've met a couple of women in their 30s who are starting to use men the way that men have traditionally used women. These women want some male companionship for dates and sex, but don't want to be in a relationship. Women's choices might not fit neatly into little boxes like they used to, but that doesn't have to be regarded as a bad thing!

Why did I write this post? I wanted to explain where I was coming from at this point of my life and show respect for the many choices out there that women in their 30s are making.

I'm 36, single and happy! If I want to get married someday, I will. And, if I don't, I won't be sitting at home crying about it. I define my life, not a man or my marital status.

Oh, and the next time you meet a 30-something single woman, try to leave the judgment and "aww, that's too bad" remarks out of the conversation. Some of us actually are single and proud of that fact!

Blow job lips


The text came in from Lawyer Boy: Leaving office and heading your way :).

Me: :-D!

I was up in my apartment and had decided to skip lingerie this evening. All I was wearing was a pair of four-inch black stilettos. (Sometimes, it's alright to be underdressed, right?) I anxiously awaited Lawyer Boy's arrival. Buzz went my phone, as another text came in.

Lawyer Boy: I'm downstairs.

Me: Is the doorman not there?

Lawyer Boy: Oh. Are you cuming down or do you want me to cum up?

Me: Oh. I can come down. I just thought that you were going to come up.

Lawyer Boy: I thought we were going to go for a drive and then get some food.

Me: Give me five minutes. Have to put some clothes on.

Lawyer Boy: Lol. Sure.

Going for a drive was likely code for something more. I had talked to Lawyer Boy a few weeks prior about how I wanted to give him a blow job in his Lotus. I had given him oral for a few minutes in his car as foreplay on several occasions. But, I had never sat in the passenger seat and finished the job. I threw off my heels and in five minutes was dressed in an outfit suitable for being out in public. I walked downstairs and kissed him hello.

"Five minutes exactly! From naked to clothes in record time, huh?" I joked.

He laughed as he said, "I didn't realize that you wanted me to come upstairs."

"Well," I replied, "I was ready for that, but now I'm in the mood for blowing you in your car."

Lawyer Boy smiled and took off in typical race-car driver fashion. While we were getting out of DC, I started kissing his neck and ears, putting one hand on his cock. When we hit a red light, he would take his hand off of his stick shift and put it on my jeans or under my shirt, rubbing whatever he could.

The moment we entered Maryland on Clara Barton Parkway, he sped up to 80mph and moved his seat belt. I lowered my head and took his cock all the way inside my mouth. That continued for a few minutes, until he pulled off the road into a recreation area. This wasn't the same park we had visited before. This was Carderock, which is run by the National Park Service. There were gates and all these signs about not being there after sunset. Hmm…I had this quick vision of us getting stopped by the Park Police and trying to talk ourselves out of getting arrested. But, I kept my eye on the prize until he drove deeper and deeper down the gravel roads of the park.

It was so dark and so quiet with acres and acres of land. That might not matter to some, but I have a huge fear of the dark. (As in, I slept with a night light until my mid-20s.) I didn't want to ruin the mood by being a scaredy-cat so I suggested that we move back toward the gate so we could make a quick get-away if the cops showed up or at least be able to argue that we were lost. (Hey — that might have worked, unless his cock was in my mouth.)

Lawyer Boy pulled up toward the entrance to the Recreation Area, and I got back to the task at hand..or mouth. I had one hand moving up and down his cock and my other hand massaging his balls. I took his cock all the way in as deep as it could go, and he came hard and fast in my mouth. When we were finished, he exhaled and said something complimentary. I kissed him and showed him how wet going down on him had made me. He put his hands in my pussy as we drove back into DC.

We decided on dinner at 2 Amys and somehow got a table without a wait on a Friday night. I noticed that several women gave me odd looks as I walked into the restaurant. I wasn't sure if it was because there were a lot of families having dinner that evening and we were clearly on a fun date sans kids.

I put that out of my head, until I got up to go to the bathroom. I walked in, saw myself in the mirror and burst out laughing. My hair looked great. My eye makeup was Chanel perfection. My outfit was cute. But, my lips were so swollen and red. Even the section between my lips and chin were puffy! I walked out of the restroom and quickly back to our table.

"Umm…why didn't you tell me I have blow job lips?" I asked Lawyer Boy.

"Huh? What are you talking about?" he replied as he chuckled.

"If you look at my face, my lips are totally swollen. It looks like I just gave you a blow job in your car. I wish I had brought some makeup or something."

I looked in his eyes, and he clearly didn't get it. Then I realized why. What guy who just came from getting an amazing blow job in his car even cares about how his girl's lips look?

"So, what are we ordering?" I inquired.

I couldn't change the fact that some other women in the restaurant were staring at me. But, my man was happy, I was still wet, and we were going to have some great pizza before even better sexl. Who was I to complain?

Mama Said Knock You Out


I was in NYC for ten days, and Lawyer Boy had a race in The Poconos. We were debating whether he should come see me in New York, or I should meet him in The Poconos. The latter option seemed easier.

"Where will we stay?" he asked.

"Motel 6, Comfort Inn, wherever," I replied, "I don't care where we go as long as we're together."

"Paradise Stream?" he suggested.

"Is that one of those couples' resorts? I would laugh my ass off if we went there," I commented. Lawyer Boy and I were never a particularly romantic couple so the thought of us at one of those resorts was rather entertaining.

He mentioned that a lot of the other guys on the racing circuit stay at a nice Best Western in the area. That sounded perfect, and he said that he would take care of the reservations.

I awoke that morning to a text message from him, which said:

Even if I'm so distracted at the race today that I place last, I'll still leave happy because I'm going to see you.

I wrote back, "You will come in first today and you will get a special prize from me later!" (You can't lose your priorities when you are in a relationship, right?)

I took the bus down from NYC and was practically jumping in my seat when I saw him in the parking lot. I got in his Lotus, and 15 minutes later, he said, "We're here!"

As a surprise, he had booked us a room at Paradise Stream, a Caesar's Resort for couples. We pulled up and saw one couple playing bacchi, another couple walking hand-in-hand coming from archery, and another couple on bicycles. Everyone was smiling so much that I couldn't stop laughing. It was like they all had drunk the Romance Kool-Aid or something.

Lawyer Boy got the key and we headed off to our room. He opens the door, and right there in the middle of our room was a 7-foot tall champagne glass Jacuzzi tub.

 Champagne Room by Cleopatra 

"Oh My God!" I exclaimed.

Then, I turned to the right and saw that we had our own HUGE, indoor, heart-shaped pool. I continued to laugh hysterically as we explored the upstairs with the king-sized round bed, mirrors everywhere, little star-like lights in every room, a massage table, a sauna, and a shower with a bench inside. There was also an Egyptian motif with pyramids and hieroglyphics all over the walls. This place was so wrong that it was right! (I later found out that this is the only room like that in the whole resort. Nice one, Lawyer Boy!)

"Why do people even leave the room?" I wondered.

The next morning, we woke up early. We had over an hour to kill before Room Service came, and put that time to good use. We skipped the pool since we had gone for a dip the night before, and bounced between the bed, the shower, and the champagne glass. I hit my head lightly, while he was doing me from behind in the shower. I didn't want to stop so I didn't say anything.

In retrospect, maybe I should have stopped. Or exhibited some restraint until after I had breakfast. Or something. This is my reenactment of what transpired after we had finished having sex and were relaxing in the shower.

Me: I'm starting to see stars.

Lawyer Boy: Maybe we should lay you…

I faint.

Yes, folks, I had so much fun that I passed out! Thankfully, Lawyer Boy caught me and put me on the floor so I didn't hurt myself. When I awoke after 45 seconds, he was over me and told me to take it easy.

I texted my nurse friend, Nicole, and she thought that I should call my doctor. I really didn't want to do that since I knew that she wouldn't understand. I decided to head home and see how I felt the next day. I had a little headache, but didn't think it warranted calling the doctor. Plus, I still couldn't stop smiling!

The jokes from our trip practically wrote themselves. It helps that Lawyer Boy and I have similar senses of humor.

"How many other girls have you rendered unconscious?" I inquired in a text.

"I'm thinking of an LL Cool J song," he texted me back. (That song would be "Mama Said Knock You Out.")

When I saw my doctor next, I did tell her what happened:

I fainted once in August, but it wasn't a big deal. I was at a Couples' Resort, and there was a lot of celebration. I hit my head slightly and hadn't eaten any breakfast.

"So, you were drinking?" she asked.

"No. I don't drink. Multiple multiples…"

The doctor just stared at me with a look of awe on her face. I felt bad since I doubt that this doctor has had one multiple orgasm, let alone several. But, hey, what can you do? The resort ain't called Paradise Stream for nothing!

The Dog Days of Dating


I won a date with a guy in New York City as part of a Charity Date Auction. He was incredibly attractive with sandy-brown hair, warm brown eyes and a very nice body. Date Auction Guy was an artist, had lived in Africa and had a different vibe (part-intellectual and part-hipster) than the guys I normally dated.

We met, hugged and started off our night with a drink at an Irish pub. Then he guided me through my first Pho experience in Chinatown. Next we headed to a bar with a private table in what used to be a trash chute. The table was surprisingly intimate despite the graffiti on the walls and the plastic “sky light” or entrance to the chute above us. We ended the night at a Swedish bar — still in Chinatown, where we listened to music and Date Auction Guy leaned in for our first kiss.

Everything felt easy and fun with him. He got me to try a lot of new places in a neighborhood (Chinatown) that I rarely visit. We went back to my place and messed around for a few more hours. (I did set some boundaries, though, and insisted that we wait to have sex until after we went out a second time. Making a charitable donation to a great cause for a date that leads to sex just seemed off to me.)

It was almost 6am when Date Auction Boy decided to leave. He invited me to spend the night at his place, but I was too tired to even get in the cab. I fell asleep with a smile on my face and giddy from our 12-hour date. He intrigued me enough to want to go out with him again in the very near future. I figured that I would see him when I was back up in NYC the following month.

The next afternoon, my friend, Ash, texted me that she was leaving work for a late lunch. I had barely eaten anything that day so I was more than happy to join her. I left the apartment in a tee shirt and shorts with minimal makeup to meet her.

At the cafe, I gave Ash the play-by-play of my evening with Date Auction Boy. She laughed out loud when I told her that he didn’t leave until after sunrise. As we were talking, Ash’s dog, Abernathy, jumped on me and started giving me kisses. (Her dog has a tendency to hump my boobs, but we are usually able to calm him down before it gets too out of hand.) Unfortunately, though, that didn’t happen this time.

I realized that my shirt was wet and wondered if Abernathy had gotten so excited that he went to the bathroom. I asked Ash,

“Did he just pee on me?”

“Umm…no…that’s not pee,” she replied.

“Eeewww! Gross!”

I tried to distract myself enough to finish our lunch. There wasn’t a lot of “junk” on my shirt, and I figured that I needed to eat something and could walk home to change clothes afterward. It didn’t seem like that big a deal so we went back to talking about last night.

“What did Date Auction Guy look like?” Ash inquired.

“Well,” I started to speak as I looked up. “Like that. OH MY GOD!!! That’s HIM!!!” I said in a combo scream-whisper.

Yes, in a city of 8 million people, I run into the guy I went out with the night before…who I wanted to go out with again…when I have doggie jizz on my shirt! What are the chances?

Date Auction Guy was meeting people only two tables away so he came by to say hello. I tried to make small talk and introduced him to Ash. That worked out okay initially or so I thought.

“Your face is really red,” he commented.

“Yeah. I’m just very surprised to see you.”

“What’s the dog’s name?” He kept petting the dog for a bit and then said, “What did you girls do to him? He looks exhausted!”

If my face was really red before, then it was a new shade of bright red by this point. We just sort of laughed off his comment and then he went over to his friends’ table. When Ash and I were done eating, I left the restaurant with my tail between my legs (or rather, my arms crossed in front of my shirt).

Date Auction Guy and I IM-ed the following week and I told him what happened. He was both amused and disgusted, which seemed appropriate. Soon after, he started dating a girl seriously and I fell for Lawyer Boy. Well, we’ll always have the trash chute bar and the café with my doggie love potion shirt. It’s not Paris, but it sure was memorable!

Nothing says a first date like The Port Authority

I went on for a few weeks last March. Some of my friends in NYC had been using the site, and I thought it would be a fun diversion from Lawyer Boy. If you’ve read my entries about Brooklyn Boy, you know that one match was a bust. Mr. Port Authority is the other guy I met through the site.

From his profile, Mr. Port Authority was totally my type. He looked so much like my ex-boyfriend, Matt, that it was almost freaky. He also loved sports and was preparing to start his surgical residency. (My hospital stories are almost as entertaining as my dating stories so I tend to hit it off with people in the medical profession.)

We spoke several times over the phone, and I was preparing to see him when I got back to DC. In our last call, he asked me to leave NYC early or go back to DC for just a night, which I viewed as illogical and too eager. I don’t understand guys who get so clingy before we’ve even set eyes on each other.

I tried to look past this yellow flag since I was interested in meeting him. Two days later, I was at the hair salon in NYC, when I got a text from him:

“I’m in NYC for the day! Want to get together?”

We started texting back and forth, and he said that he was in the City to drop some info off at hospitals and to try to see me. Hmm….the Cling-O-Meter is rising and that’s not a good thing.

I knew enough about the residency match process to know that the results were coming out in a week. This guy is clearly not Type A or anything close to that if he waits to speak with hospitals until the 11th hour. His stock is falling since I’m far too motivated to deal with someone who isn’t at least a Type B.

I asked him where he was and he threw out an address that was THREE blocks from my family’s apartment in NYC. I exhaled and tried to convince myself that this was just a coincidence. I don’t remember if I told him where in NYC my family lived, but it was a tad creepy.

“Where were you thinking of meeting up?” I texted.

“What if we meet at The Port Authority for a hug and coffee before my bus leaves?”

The Port Authority? Who wants to meet someone for the first time at The Port Authority? That building is just one notch above a sewage treatment plant. My friend, Amy, summed it up perfectly when she said, “Does he want to kidnap you and take you to New Jersey?”

I decided to pass on this tempting offer [insert sarcastic eye roll here] and suggested that we wait to meet until we were both back in DC. By this point, my friends thought he was a stalker. I thought he was needy and socially-awkward. Regardless, Mr. Port Authority was making Mr. Starbucks look good, and that’s not saying much.

Brooklyn Boy — Part II or What Not to Say on a Date

I was really looking forward to my date with Brooklyn Boy and saw the evening as a chance for us to get to know each other better. We went to a nice lounge in Chelsea and a casual, Asian-fusion restaurant in Union Square. I’m not one who requires a guy to be overly chivalrous or attentive, but I do notice those things. I offered to pay my way at the lounge and at dinner, and he took me up on both of those offers.

That might have made more sense had he not gone on – almost ad-nauseam – about how he’s trying to figure out how this relationship can work if we live in different cities the majority of the time. (Hmm…I didn’t know we were in a relationship yet.) I said that we would see each other over inauguration, which wasn’t too far off. He replied that a month was a very long time to wait. Seriously? We don’t even really know each other. Does he want me to run in the opposite direction? (That tends to happen if someone gets super-clingy with me after only a few dates.)

The night got worse when he tried to kiss me. Much like I did on our first date, I told him that I wanted to take things slowly and didn’t want him to be the rebound guy. He then started negotiating like we were 15, and he was trying to get me to have sex with him for the first time:

“Just a little kiss. It’s not a big deal.” It is to me.

“A kiss isn’t taking things quickly.” At our age, a kiss rarely stays at just a kiss for very long. Plus, isn’t the physical connection the easy part? It’s much tougher to find someone with whom I connect emotionally and intellectually.

“Do you not believe in PDA?” Yes, if I’m comfortable with someone.

“Relationships are about compromise.” But we aren’t in a relationship yet…

“Are you a prude?” I tried not to laugh out loud at this. The boy has no idea what I freak I can be…with the right person.

The prude comment really made me feel like I was 15 again. It got worse when he cornered me outside of the bathroom on our way out of the restaurant and kissed me. He didn’t ask if that was okay. He just did it. I went along somewhat reluctantly.

The seven-second kiss was one of the worst kisses of my life. Brooklyn Boy kisses with the FLAT part of his tongue. He doesn’t use the tip of his tongue. He doesn’t maneuver the flat part of his tongue gently. He just came at me like a hyperactive dog. Ugh!

To make the evening even more bizarre, Brooklyn Boy relayed a Woody Allen joke to me… about rape. If you care, read the section about Harlene Rosen here. Rape is never funny. After he saw my reaction and I emphatically stated, “That’s not funny,” he apologized. I accepted his apology, but it just didn’t seem sincere. I felt like he really didn’t get how inappropriate it was to relay that story. Period.

I ended the night, thinking that I might see Brooklyn Boy again. (I know. I need to make better guy choices.) But, after sleeping on the prude question and rape joke, I realized that I don’t care to see him again. I don’t know if he doesn’t respect women or just doesn’t get them, but either is a deal breaker for me.

He contacted me this week, and I wrote back an e-mail that I just didn’t feel comfortable with some of the comments that were made and wished him the best in 2009. He then asked me to tell him what he said. I kept my response brief (asking me if I was a prude because I didn’t want to kiss you and telling the Woody Allen rape joke made me feel uncomfortable), and he wrote the following:

“Boy was I misunderstood. The Woody Allen joke was something I had heard and wasn’t my invention. I thought I had put forth the disclaimer and apology once you stated that you worked with abused women. I know it’s a serious matter…Please contact me again. Go with what you felt when you talked to me not what you added to the event which took place in your memory. I really do like you and would like to see you again.”

Wow! So, if you didn’t come up with the joke and apologize afterwards, that makes it OK? And, I had to try not to laugh that he’s making it sound like he’s misunderstood and that my memory is faulty.

I actually don’t disagree with his take on what was said, but I don’t care to engage him further. He clearly doesn’t get that it was wrong to relay the joke at all. I sent him a one-liner asking him to respect that I don’t care to communicate further to which he wrote me back another long paragraph. I’m not replying anymore. How much do I have to say to a guy who made me buy my own dinner, thought it was acceptable to tell a joke about rape, and kissed me with a flat tongue when I didn’t even want to be kissed :p?

Brooklyn Boy — Part I

I recently ended a relationship with a man I loved…a lot. I know that it was the right decision to break it off with him, but it still hurts.

I'm not a serial monogamist and know that I'm not ready to be in another relationship anytime soon. But, I still enjoy dating and going out for drinks with guys. So, I gave this Brooklyn Boy a chance.

He and I met earlier this year for coffee when I was wondering if I was ready to start dating other people. (I wasn't, as I was far too in love with Lawyer Boy, but I tried.) If I close my eyes and imagine the perfect guy for me physically, Brooklyn Boy fits the bill. Think 6'2" tall, dark and handsome with an athletic build. Brooklyn Boy's inside is as appealing as his outside. He's motivated professionally and well rounded with a love of traveling, foreign languages and sports. I like being able to talk politics with someone one minute and NCAA basketball the next. The fact that he spoke quite a bit about his family and how close they all are increased the value of his portfolio for me. Meeting someone for a quick coffee usually doesn't leave me wanting more. With Brooklyn Boy, it did.

So, now that I am officially single, I decided to e-mail Brooklyn Boy. He was game for getting together for drinks at a bar in Gramercy. The bar was modern, yet romantic, with dimmed lighting, lots of candles and velvet couches. On a Monday night, it wasn't too crowded for us to hear each other. The more we talked, the more I wanted to talk more.

He asked me when I was last in a relationship. I was honest with him and said that I recently ended something serious. I commented that I hoped he and I could keep getting to know each other and see what happens. Brooklyn Boy seemed fine with that…or so I thought. We were just sitting there on the couch, and out of nowhere, he tries to kiss me. Not a little peck, but a full-on open-mouth kiss. We haven't even spent more than three hours together cumulatively, and he's acting like we're at a frat party! (20-something City Girl would have been open to that, but 30-something City Girl is not.) I was totally caught off guard, but managed to steer the kiss to just a peck on the mouth. Thankfully, he didn't push it. We ended the night with another peck and agreed to see each other next week.

Was it naive of me to think that he wouldn't push it on our next date? Maybe. But, I was looking forward to spending more time with Brooklyn Boy and could not have foreseen just how bizarre that date would be.