Help me pick my best worst date!

I've decided to enter a contest for The Best Worst Date. I've shortened two of my posts to satisfy the 250-word limit for submissions, which was tougher than I anticipated. Please let me know which you prefer or if there's another dating adventure that comes to mind. (FYI - I don't think that Purple Thong Boy can count since that wasn't technically a date. Also, given the audience, I'm trying to keep my submission PG-13.) Thanks!

Option #1

1. He wanted to meet at Starbucks. (That’s not a deal breaker, but it’s not a creative first date spot either);

2. We agreed to meet at 11am, but then he kept insisting that we said 10am;

3. I arrived and found him having breakfast with his roommate. He didn’t apologize or introduce us;

4. He didn’t even offer to pay;

5. He maligned my choice of beverage as unhealthy;

6. He asked if I would drive him to the bank to cash a check. Who does their banking on a first date? (I bit my tongue because we have a friend-in-common);

7. He got annoyed when I didn’t know where the nearest branch of his bank was located;

8. He asked me to take him shopping to get things for his new place;

9. He wanted me to drive him to his apartment to drop off his purchases;

10. He raised his voice when I didn’t drive the (longer) route he recommended;

11. He wore a fanny pack. (Initially he carried it over his shoulder, but then he moved it to his waist);

12. He kept talking about his pedigree. "I fence. I ride horses. I drink only the finest Italian wines. I have a flat in London;" and

Unlucky 13. After our "date," he called a friend to ask why I won’t go out with him again. Are you kidding me? He doesn't need a girlfriend. He needs a driver and a personal assistant!

Option #2:

We had been at the lounge for an hour when Brooklyn Boy tried to kiss me. Much like I did on our first date, I said that I wanted to take things slowly. He then started negotiating like he was a teenager trying to get some action:

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

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

“Are you a prude?” Seriously?

He let it go, but two hours later after paying my way the entire evening, he cornered me outside of the bathroom and kissed me. He didn’t ask if that was okay. He just did it. I went along reluctantly.

The next seven seconds were horrible! Brooklyn Boy kisses with the flat part of his tongue. He doesn’t use the tip or maneuver it gently. He just came at me like a hyperactive dog.

Then he relayed a joke to me… about rape. When I looked at him in shock and emphatically stated, “That’s not funny,” he apologized. I accepted his apology, but felt like he didn’t understand how inappropriate it was to relay that story.

I knew I wouldn’t go out with him again, but Brooklyn Boy had other ideas. I finally asked him to stop contacting me. How much do I have to say to a guy who made me buy my own dinner, told a rape joke, asked if I was a prude, and kissed me with a flat tongue when I didn’t even want to be kissed?

Laughing at a comic isn't always a good thing

2005

In 2002, Baseball Boy and I went out on our first date to dinner and a comedy show at the DC Improv. We saw a comic who had found success in TV and film in the 1990s, but was now doing stand-up at a small venue. He still put on a great show, though, and a few of his bits made me laugh so hard that my stomach hurt.

Three years later, Funny Boy returned to DC, and a group of us went to see him perform. I got up in the middle of the show to stretch. While in the lobby, a large, handsome man approached me. It turned out that he was Funny Boy’s bodyguard, Greg. I was surprised that Funny Boy needed a bodyguard, and Greg agreed with me that he didn't. He thought that Funny Boy just liked the attention that a bodyguard attracted. Interesting. Greg and I talked during much of the show, and he asked if I wanted to go out for a drink afterward. I had plans with my friends that night, but I told Greg that I would call him before he left town.

Two nights later, I was driving back from an Orioles game and decided to see what Greg was up to. Funny Boy was starting his show soon, and Greg suggested that I come by the Improv to grab a drink. I arrived at the club and was glad that I did. I spent most of the night hanging out with the opening comic and Greg in the back of the venue, and we had a blast.

After Funny Boy was done, he came to the back and looked at me. He asked if I would come out with him and some friends to a nearby lounge. I wanted to spend more time with Greg, and thought Funny Boy would be well, funny, so I said sure.

Funny Boy had also invited some other girls to the lounge. From their outfits, it appeared as though they were in the entertainment industry. I don’t mean that with judgment behind it, but it’s not that tough to spot strippers in an Ann Taylor/Banana Republic/J Crew town like DC.

We arrived at the lounge and one of Funny Boy’s friends from high school joined us. He also had asked a pretty, petite Indian girl to meet him there. She seemed very sweet and brought along two of her friends. So, there we were at the table: Funny Boy, the bodyguard, three petite Indian girls, the high school friend, two strippers and me. Remember that game on Sesame Street – which one of these is not like the other? Well, at this table, I definitely didn’t blend, but that didn't phase me.

The strippers kept going to the bathroom to powder their noses. The powder was not the type that you could purchase at a cosmetic counter. The sweet girl that Funny Boy had invited seemed uncomfortable, but at least she had her friends with her. I talked a lot with Greg and the high school friend, and the mood lightened (and livened) up when we all started dancing.

I took a break from the dance floor, and Funny Boy and I started talking one-on-one. He said that he was attracted to me. I responded,

“Thanks. That surprises me, though, since I’m not your type.”

“Why would you say that?” he asked.

“Because I’m not a petite Indian girl or a stripper.”

“Well, you are the girl I want to leave with.”

I was flattered, but I also tried not to think too much of it. I felt as though he was attracted to me because I seemed like a challenge. And, I wasn’t sure if I was even attracted to him.

We left the lounge, and one of the strippers was so out of it that she could barely walk. Funny Boy told Greg to make sure that they were okay and take them home. (I realize that Funny Boy was paying Greg, but I would hope that my friends wouldn’t task someone else with helping me out if I wasn’t feeling well.)

Funny Boy and I walked to his hotel around the corner, and he invited me up to his suite in The Mayflower for a drink. I told him that I would be happy to join him for a drink, but that I wasn’t going to sleep with him. He was fine with that, and suggested that I meet him upstairs in ten minutes.

In ten minutes, Funny Boy had turned on light jazz, lit candles in both rooms and changed into a t-shirt and flannels. He became very intense, very quickly. I was talking about how I hoped that the girls were ok. I asked if the drinks were very strong at the lounge, and Funny Boy got very defensive, insisting that he doesn’t drink alcohol. (OK. Fine. Calm down, buddy.) He was heading to New York City after DC, and I made some silly comment with a Brooklyn accent. Then, he got very offended.

“Why are you doing impressions?” Funny Boy inquired.

“Umm…because it’s funny. I say things in different accents all the time,” I replied.

“You are not a comedian. You are not supposed to make jokes. I am a comedian. That’s what I do.”

“Umm…ok.”

I wasn’t sure if I was interested in Funny Boy before I went up to his room, but now I knew that I wasn’t attracted to him. Within a minute, he got on top of me and started kissing me. He was one of those kissers who just sticks his tongue down your throat with no skill, direction or passion. I sensed by the movement in his flannel pants that he was excited, but each second with his tongue so far down my throat was one too many. I felt as though I was at the doctor’s office and he was checking to see if I had strep. Eww!

I excused myself soon after that. As I exited the hotel, Greg called and we had a nice talk. Greg was articulate, caring and fun. If he didn't live in LA, I would have gone out with him again. Funny Boy, by contrast, gave me his number, and I promptly deleted it. It's a good thing when a guy makes me laugh because of his humor and personality. It's not a good thing when a guy makes me laugh because of how he kisses.

A smooth second impression

2007

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 café, 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!

Tabasco -- what do you put it on?

1994

Sometimes I don’t have the best filter. That can be both a strength and a weakness, depending on the occasion, the company and the comment. At least I was with friends when the following conversation transpired at a restaurant:

“Do you like Tabasco?” a friend asked me, as he doused his eggs with the hot sauce.

“Not when it's in my crotch.” I replied.

[Complete silence at the table, until everyone starts cracking up and asking me to explain.]

Yes, folks, in case you were wondering, it really, really stings if you get Tabasco in your privates. I found out the hard way when I was at my apartment with UConn Boy. I was doing some work as he was eating wings with hot sauce on the edge of my bed.

UConn Boy finished dinner and was in the mood for some dessert. He moved right in for the Promised Land, which was great for the first few seconds, until my eyes started to water from the burning pain.

I let out a high-pitched scream, leaped out of bed and ran to the shower. We eventually picked up where we left off, but only after it was clear there was not a drop of Tabasco anywhere on him.

The next day he told one of his friends about what had happened, and I told one of mine. One friend was a regular at our favorite bar and the other was a bartender. By the time we got to the bar the following evening, most of the regulars and staff had heard the story. No comments were made as we sat down, but one person…then another…and then another…came by and dropped a bottle of Tabasco in front of us. We must have had a dozen bottles by our seats, and we couldn’t help but laugh.

Around this time, Tabasco had launched a new ad campaign. The slogan was “So what do you put it on?” The commercials featured different celebrities and their favorite use for Tabasco. UConn Boy probably had the best answer to that question, although I don’t recommend trying that out at home.

It's a Dick in my In Box!

2007

Last spring, I finally came to the realization that Internet dating is not for me. I’ve done it a few times over the years, but I’ve found that the guys I meet online typically fall into one of two groups:

1. Want to get married and/or have children ASAP. Such a cavalier approach to something as serious as marriage freaks me out. I am in no rush to get married, and want to really know someone well before I stand in front of him and say that, “Yes. This is forever.” When guys from online sites talk about relationships and commitments by the second date, I never stick around for the third; or

2. Just want to get laid. Now, I’m fine if people are up front about that, but don’t place or respond to an ad about a relationship, when you really just want a casual encounter.

Tennis Boy fell into the second category, although I had initially thought we were looking for the same things when we met in 2007. He was well educated, attractive, international and athletic. Our first date consisted of taking his dog for a long walk in the park. He seemed respectful and considerate – to both the dog and me. I don’t keep a tally as to how well a date is going, but if I did, he would have scored quite a few points.

For our second date later that week, we went to a lounge. Again, he did and said everything right. Conversation with him was easy, and he had a good sense of humor. He paid for my drinks. He walked me to my car at the end of the night. He gave me the tiniest kiss on the lips (closed mouth). He was heading out of town the following week and then I was going to be out of town, but we planned to see each other when I got home.

Two weeks later, I was back in DC, but he had a bad cold. We texted and e-mailed a few times, and I figured that we would eventually go out again. I wasn’t pressed about it, though.

So, imagine my surprise, when I saw that I had an e-mail from him at 1am. The subject was “I’m thinking of you,” and there was an attached photo. I clicked on it, and stared at my computer screen with a look of shock on my face.

Tennis Boy had sent me a photo of himself naked. If you think this might have been an artistic or subtle shot, think again. He took the picture from the neck down and in the center of the shot was his hard dick. Tennis Boy was sitting on a stool as he was posing, and in the background was his disgustingly dirty kitchen floor.

When I told a friend the story, she asked, “How did his dick look?” I guess that didn’t even matter to me since the e-mail was so inappropriate that I just deleted it. Another friend commented, “It is never a good thing to send genitalia pics online.” For serious! How did he go from Mr. Chivalry to Mr. Dick in my In Box?

I didn’t reply to that e-mail, but he wrote me again. He intimated that he thought I was more open to those kind of things. Eww! Again, I didn’t reply.

I was telling the story to a few friends at a local bar, when one of my boys said, “Wait a minute. Is his name…?” Yep. From the basic information that I shared at the bar, my friend knew the guy, and was not necessarily surprised that he did this.

Well, I guess I should feel lucky to have gotten out when I did. Someone else can deal with Tennis Boy, his fetish for unattractive naked self-portraits, and that gross kitchen.

Yes, I broke my nose having sex

1995

GWU Boy and I were an almost-lethal combination. He was destined to be a rebound guy from the start. I was still in love with my ex, who happened to be one of GWU Boy’s friends. I also was pressuring GWU Boy to get serious at a time when he was interviewing for teaching positions outside of DC. (Yes, I know that this screams, “dysfunctional.” In my defense, the year was 1995, and I didn’t make the best choices back then.)

Sexually, we were especially lethal. When we were together, we destroyed everything in our midst. What fell prey to our path of destruction? His futon. His brass bed. A lamp. It got so bad (and obvious) that his Catholic mother bought him a cross to put over his bed. Can’t blame her for trying, but if she was looking for a chaste couple, she needed to look elsewhere.

A couple months into our relationship, we weren’t getting along that well. He neglected to mention that he would be out of town for a job interview over my birthday. So, my birthday came and went without any acknowledgment from him. I was beyond pissed, but somehow managed to overlook that when I saw him at our bar (RIP GG Flipps). I rarely drink, and this night was no exception. GWU Boy, by contrast, was quite drunk. We bickered for a little, and then he apologized for missing my birthday. I accepted, and we went back to his apartment.

It took about five minutes for us to end up in bed together. (Sure you didn’t see that one coming, huh?) I was on top, facing him, with my hands behind him on the headboard. I was getting in the zone, as he leans up to kiss me. That would have been great, except for the fact that his head hit my nose at such a high velocity. I was brought back down to reality by the excruciating pain and the fact that there was blood everywhere.

“OWWWW!” I screamed.

“What happened?” he asked.

“I think you broke my nose,” I replied.

“Umm…can we finish?” he implored. (Yes, he REALLY said that.)

“Are you kidding me?” I said. Now, I’m usually all for winning one for the team, but this was not the time for that. I knew that I needed to get to the ER.

We went to the ER, and being the gentleman that he is, he refused to go inside the hospital with me. So there I am, bawling with a broken nose and a guy who is adding insult to injury. I was embarrassed about what had happened so I only told one doctor in the ER the full story. He wrote on my chart that I had "hit my head." That seemed like the right thing to do at the time, until the nurses started wondering if I was the victim of a domestic assault. Seven different hospital employees asked me if I was in an abusive relationship, which just made me cry more.

My septum was badly deviated, and I was sent home with painkillers and told to take it easy for a few days. GWU Boy drove me home and then went back to the bar...to drink more! Nice!!! I called Orioles Boy, another guy who I had been seeing on-and-off for a few months. (Yes, I wanted to be in a committed relationship with GWU Boy, even though I was hooking up with another guy on the side and in love with a third guy. Can I use the fact that I was only 21 as my justification for that behavior?) Orioles Boy ended up taking care of me all weekend, which won him huge points.

Now, I can laugh at what happened. It is pretty funny that I broke my nose having sex. When I finally went to see an ENT and plastic surgeon about my septum, they said that my story was the most original answer to their routine question of “How did you break your nose?”

When I’m in a bad relationship, it sometimes takes me a while to get out of it. But, the nose break was just the slap in the face – literally and figuratively -- that I needed to get out of a relationship that was doomed from the start.

PS GWU Boy and I are friends again – without benefits. He’s not a bad guy; we were just young, stupid and not a good match for each other. At least I got a great story and a cute new nose out of it ☺!

Purple Thong Boy

2002

I met Michael at Cheesecake Factory on a Saturday morning. That should have be enough of a sign that he wasn’t going to be my Prince Charming, but he was very attractive and a Georgetown grad so I gave him my number.

We would meet for drinks now and then. It wasn’t serious (no love and no sex), but he was fun to hook up with. Michael always seemed to travel with at least one – and often, several – of his boys. I would get calls from his best friend, Charles, and some nights, both of them stayed over at my place. Back then, I was living in a studio and just had a bed and no couch so sleepovers at my place were quite cozy. But, Charles was always very respectful and Michael was amusing so it wasn’t a problem.

On one particular day, I was at work and got a call from Michael. He and his friend, Dylan, wanted to take me out to lunch. I rolled up to the bar at Friday’s and found them both already buzzed at 1pm. This Friday’s doesn’t get much traffic during the day so I felt really bad for all the senior citizens having lunch there. Michael was all over me like it was 3am and we were leaving a club.

He then started talking to Dylan about how much he liked kissing me and wouldn’t Dylan like to kiss me. Dylan seemed open to it, and I replied, “Sorry. I’m not MCI. I don’t do Friends-and-Family.” (An MCI reference is dated, I know, but those ads were all over TV back then.)

I had to head back to the office, but Michael and Dylan mentioned that they might come over later and we could go out to dinner. I just told them to give me a call. Several hours later, as I got home from the gym, my phone rang. It was Dylan, saying that he and Michael were coming by with Chinese food in an hour. I told him that I was pretty beat, but if it was just for a few hours, that was cool.

Shortly after the call, Dylan showed up at my door with a bottle of wine.

“Where’s Michael?” I asked.

“He went to get the Chinese food. He should be over in a little.”

An hour later, I was starving and Michael still wasn’t here. Dylan left a message for Michael, but he didn’t call back. By this point, the wine bottle was almost empty and I hadn’t had a glass. As Dylan got more and more buzzed, he kept moving closer and closer to me. Then, he offered to give me a foot massage. Umm…no thanks.

Finally, I just said, “Is Michael really coming over?”

“Well, I think so. But, you know him. He’s probably out with another girl.”

“We’re not in an exclusive relationship,” I replied. “He’s free to date whomever he chooses, as am I. I just don’t feel comfortable having you over if he’s not coming.”

“Oh. Okay. Can I just use your bathroom?”

“Sure,” I said.

I kept watching the movie and was trying not to fall asleep. But then, I noticed something out of the corner of my eye. Dylan came out of the bathroom, wearing nothing but a lavender thong. What kind of guy wears a LAVENDER THONG? (Most black guys I know wouldn’t be caught dead in a thong -- ever.)

I tried to look away because it was like watching a train wreck. He then started prancing around in the thong, jiggling his package. “You want some of this?” he asked.

“NOOOOO! Put some clothes on and get out of my place.”

“Don’t you like me? I know that I could satisfy you. Michael said that you were really fun.”

“Get the hell out of my place! NOW!”

He put on his clothes and left. The image of him in the thong still haunts (or amuses?) me to this day. It was so wrong that it was funny. No guy should be wearing a thong unless he’s a professional bodybuilder. And, Dylan was definitely not that.

A few days later, Michael called and I told him what happened. He had absolutely no idea that Dylan had even come over to my place, let alone under false pretenses. When I told him the purple thong portion of the program, he was livid. Michael and Dylan worked for Michael’s father’s company. Dylan lost his job because of this since Michael and his dad thought this was so irresponsible.

Even though I only spent a few hours with Dylan, I will never forget him. Thank you for the laughs, Purple Thong Boy!

Brooklyn Boy -- Part II (or what not to say on a date)

2008

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 at: http://en.wikipedia.org/wiki/Woody_Allen. 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

2008

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 sure that I’ll write more about my relationship with Lawyer Boy in future posts, but my emotions are a bit too raw to do that right now.)

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 naïve 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.

A horrible first date

2007

It was September, when a friend IM-ed me about fixing me up with this guy he had just met. I'm not one for blind dates, but I was told that he was funny, attractive, educated and second-in-command at the embassy.

"Which embassy?" you might be asking.

Well, I probably shouldn't say, but I viewed the embassy connection as a huge plus since I had lived in his country for a year. I was looking forward to the guy's call and saw some potential. Boy, was I wrong! Read on to find out why our first date was also our last:

1. He picked Starbucks as the meeting place (Picking Starbucks is not a deal breaker on its own, especially for a casual and quick get together, but it's definitely not the most creative place for a first date);
2. He asked when I was available. I said, "11." And for the next 15 minutes on the phone, he kept insisting that we were meeting at 10. The following morning, he tried to get me to agree to 10:30. 11. I told him that it was fine if he wanted to grab breakfast on his own, but he insisted that he could wait until 11;
3. I rolled up to the Starbucks and noticed that he was already having coffee and a muffin with his roommate. Huh? He did not apologize nor did he introduce us;
4. He did not offer to pay (I'm cool with paying my way, but an offer is nice);
5. He maligned my choice in beverage from Starbucks as unhealthy. Since he's neither my Mom nor my husband, I was not cool with that;
6. He then asked if I would drive him to the bank so he could cash a check. Who does their banking on a first date? I decided not to tell him what I really thought of him at this point and ride it out because we have a friend-in-common;
7. He got annoyed when I did not know where the nearest branch of his bank was located;
8. Next, he asked me to take him shopping since he needed things for his new place;
9. He became cross when I turned left, instead of right, to get to the store, despite the fact that I learned to drive in this city and know where I'm going, whereas he just moved here and doesn't have a car;
10. He then asked me to take him to another place to drop off the items he purchased at the store;
11. He was wearing a fanny pack. (Initially he carried it over his shoulder, but then he put it around his waist -- and kept it there);
12. He did not stop talking about himself and his pedigree. "I fence. I ride horses. I drink only the finest Italian wines. I have a flat in London;" and
Unlucky 13. After our "date," he was deluded enough to call a mutual friend to say how much he likes me and express his confusion as to what went wrong?!? Are you kidding me? He doesn't need a girl. He needs a driver and a personal assistant!

Mr. Starbucks, as I refer to him now, called me twice after this "date." I, of course, let his calls go to voicemail. In his messages, he asked me to call him and mentioned us getting together again. I pressed delete. Can you blame me?