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.