My _ _ _ _ _ Anal Encounter.

December 31, 2013

I met Doran in 2004 on Jdate. Doran was a super sexy, super smart Israeli who worked as a finance professor at a college in the city while working on his doctorate.

We met for coffee early one Saturday morning and I was instantly attracted to him.

Coffee turned into brunch and before the check came he asked to see me again that night.

We met in Union Square on a hot summer night and went to the movies. We saw The Notebook and as tears fell out of my eyes watching Allie and Noah leave this earth together hand-in-hand, Doran reached over, wiped away my tears and kissed me.

Dying to get naked with this guy, we headed back to Doran’s dungeon…I mean apartment.

His place was a dump! It was dark with exposed filthy brick walls, a cement floor, one small window with bars facing a brick wall and the best part was….there was no bathroom. The building had a communal bathroom on each floor…can I get an OY?

Doran offered me a drink, which of course I refused for fear that I would need to use the bathroom.

So we just got down to business and started making out. At some point I looked over and saw a bug crawling near my bra on the floor. But considering that Doran was an amazing kisser and the first guy from Jdate who got my panties wet, I just closed my eyes and ignored the urge to recommend a great exterminator.

Doran called me early the next day and asked to see me…AGAIN. I couldn’t believe it! Three dates in two days! This super hot ridiculously smart Jewish guy who had his shit together (minus the apt) was really into me!

Too traumatized to go back to his apartment I invited Doran uptown. It was the 4th of July so we planned to walk towards the East River to watch the fireworks.

After making out near the FDR for a while, completely oblivious to the fireworks overhead, we headed to my apartment.

It was pretty clear that Doran wanted to have sex with me. But up to this point I had only been with Will and I wasn’t ready to have sex with someone I had only just met the day before.

But Doran was so sweet…surely he would understand!

After I told Doran that I was not ready to have sex with him he asked for the obvious alternative…..


I just told him that I wouldn’t have sex with him because it was too soon in our relationship and he thought I would be comfortable with anal!

Of course he did!

After I told Doran that I was not ready to have him enter through the back door he left through the front door…never to be heard from again.


Vince (cute 31yo from Match): I think you’re really hot, You want to have some fun in my bedroom?

Me: Uh….Thanks! Sorry, but I’m not that kind of girl. I’m looking for a relationship.

Vince: It was worth a shot!

A few days later…

Vince: Hey beautiful! How are ya? I would really like to take you out.

Me: I’m not looking for just sex! I’m looking for a relationship. Are you up for that?

Vince: Sure. I think you’re really hot, lets go out sometime.

Me: Ok…

Vince called me on Thanksgiving and we had a good conversation for over an hour. He apologized for his 1st email and told me that he really wasn’t that kind of guy.

We ended the phone call with him telling me to text him tomorrow.

Me: Hey! How’s your day going?

2 hours later….

Me: What? Change your mind?

Vince: Yeah, sorry.

Me: Can I ask why? Thought we had a good chat.

Vince: We did. I’m sorry. I’m just not ready for a relationship.

Me: I don’t have “marry me” written on my forehead!

Vince: Yeah I know. But I have commitment issues and you seem like a nice girl. I don’t want to hurt you.

Me: Ok. Thanks for the heads up. Good luck.

Fast-forward 1 week….I got on the train headed for work and just as I sat down I received a text.

Vince: Did you just get on the train?

Me: Yeah!?!?!?!?!

Vince: I’m on the same train as you. I’m sitting a few rows back.

Me: That’s nuts. I can’t believe you recognized me.

Vince: Yeah, you look like your pictures. I saw you yesterday too but I didn’t think you’d want to hear from me.

Vince and I continued to text the entire train ride into the city. As the train pulled into the station, I was finally able to turn around and get a glimpse of my non-committal train stalker….Wow, he’s kinda hot!

Vince and I texted throughout the day and once again he asked me out. I was weary, considering he told me that he had commitment issues but randomly seeing each other on the train changed my mind….it was meant to be!

Friday night rolled around and Vince told me that he wasn’t feeling well. It was pretty obvious that he didn’t want to talk or see me.

Saturday afternoon I texted him to see how he was feeling and he didn’t respond.

Annoyed, that Vince was blowing me off, again, I signed back on to Match and gave my # to a guy named Joe that I had been emailing with for about a week. Six hours later Joe and I made plans to meet at a bar.

Huge mistake. HUGE! My hastiness resulted in not talking on the phone with Joe before meeting him. I didn’t screen properly and I was forced to have a drink with a very very very nice guy who, how can I say this nicely, who was a few cards short of a full deck.

On my drive home from my very sad date with Joe, I texted Vince.

Me: Because of you I just went on a horrible date.

Vince: Ha Ha! How so?

Me: You didn’t text me back today so I wound up going on a date and it was terrible!

Vince: You need to screen better!

Me: Yeah, no shit!

I was all dressed up with no where to go so when Vince said that he wanted to see me….I invited him over.

Vince and I talked for a while. Then we started making out. Which really wasn’t fun or exciting. His skin was waxy and cold, his lips didn’t move. I was kissing a dead fish. I felt nothing down there….Zip! Zero! Nothing!

To top off the night, when I attempted to find out what Vince was packing he stopped me within seconds telling me he was going to cum. Huh?

Yes ladies and gentlemen…I found another premature ejaculating fella. Must be the new fad. Everyone seems to have it lately! Two in one month! Yippeeeeee!

When he asked for a blowjob I refused.

Sorry dude but a 10 second bj really isn’t worth the effort. It takes me longer to put my hair up in a ponytail.

Vince was right…I do need to start screening better!

My sister recently recommended a book to me, which I downloaded on my Kindle yesterday around noon. I couldn’t put it down. I stayed in bed all day reading completely absorbed in this amazingly depressing love story.

By 6:00pm I finally forced myself to turn off the Kindle and get out of bed so that I could start getting ready for my hot date at 8:00pm.

You know you are in trouble when you would much rather stay in bed reading than go out on another blind date.

Rich was a 45 year old very short never been married Jewish man who contacted me on Eharmony a week or so ago…I really wasn’t into him.

There were no major red flags as we worked our way through the Eharmony communication stages until I asked him, “Describe an interest you have that you would truly hope your partner could share with you.”

Rich’s Answer: “Just the interest of having fun, laughing and enjoying life no matter where we go or what we do or whatever activities we come up with. I could also go with the interest in having a child someday…that is definitely an interest I hope she would share with me.”

He couldn’t come up with one interest! Not one??? Reading? Watching football? Traveling? Jerking off? Not one! Oh and the kid thing was just fucking creepy!

I kept telling myself, “What’s one hour? Go on the date. You never know.”

So I agreed to go out with him but quickly knew that I was in trouble. When I asked him to suggest a bar to meet at for a drink he offered….TGI Fridays!

I texted him when I got to Fridays and asked him if he was inside? Seconds later I saw a very little man, with a limp, head into the restaurant. I stood in the parking lot for a good minute deciding if I was going to go in. My mind was racing trying to come up with a good enough excuse to get out of this date.

But then I reminded myself that I could never do that to someone. I would be horrified if someone did that to me. I could make small talk for an hour.

I ordered a pinot grigio.

He ordered a non-alcoholic Berry Strawberry Smoothie and repeatedly commented on how awesome the smoothie was but how surprised he was to taste watermelon. Watermelon is not a berry!

The date really took a turn for the worse when he asked me if I liked Kohl’s?

Three bad dates this month…one worse than the next! I may take an online dating hiatus.

T.G.I.F readers….

This Girl Is Frustrated!

Not all of my blind dates have been from online dating. My friend Wendy back in 2003 tried being a matchmaker and set me up on a date with the son of a contractor she worked with.

I knew nothing about him other than his age (late 20s) and that he worked for his father who owned a very profitable exterior restoration company.

I asked Wendy before agreeing to go on the date what the guy looked like. Unfortunately, the only time she had seen him was on a job site. It was the dead of winter and she couldn’t get a good look at him since he was all bundled up.

Regardless, I agreed to go.

Jay called me to make plans for a Friday night. He offered to pick me up at my building so I gave him my address.

The doorman called to tell me that Jay had arrived. I left my apartment and headed downstairs. I exited the elevator and saw who was standing on the sidewalk…..

Mr. Clean’s son!

Mr. Clean

He was tall, husky, bald and wore one large thick silver hoop earring in each ear.

Oh boy…here we go.

Jay and I hopped in a cab and headed to a restaurant on 1st Ave.

We were seated at a table and then Jay took off his winter coat…

He was wearing a shiny striped long sleeved blouse with a matching tie.

His whole look was just confusing. Fucking Wendy!

We ordered drinks and started chatting. I could tell that Jay was definitely nervous, so when he downed his first pint of beer and ordered another one before I had taken two sips of my dirty martini, I really didn’t think too much of it.

But then he ordered his third, before I was halfway through my 1st.

And then he ordered his fourth, before our dinner arrived.

And then he ordered his fifth, then his sixth, then his seventh…..

Do you see where I’m headed here?

By the time our dinner was finished he drank 12 pints of beer. Yes, I counted.

Jay was bombed. He was slurring his words, he couldn’t keep eye contact with me and when his hand found its way to my thigh, I suggested we get the check.

We left the restaurant and headed outside to grab a cab. I tried to ditch Jay by telling him that it was silly for him to take me home since I was headed uptown and he was headed downtown, but he insisted.

Jay was way too drunk and uncoordinated to put his arm in the air to hail a cab so he decided that it was my job. Apparently his job was to try and stay upright with the assistance of a mailbox.

Considering it was a freezing cold Friday night, cabs were far and few between.

Several minutes passed without success when I heard Jay yell out to me, “Yo Dorothy, its cold out, get us a fucking cab!” For a second I didn’t know what he was talking about. Was he so incredibly drunk that he just forgot my name?

And then I realized what he meant. I was wearing red stilettos…like Dorothy!

Apparently, all it takes is 12 beers (and a satin man-blouse) to get to Oz.

Dear Shithead:

I recently accepted a new job and one of the 1st things I thought about after making the decision to change jobs was that my new office is relatively close to yours.

I am petrified of running into you.

I told everyone I know, “I’m going to run into Shithead!” “I just know it!”

But everyone’s response to my worrying was, “Stop!” “You’re being ridiculous!” “It’s a big city!” “I’m sure you won’t run into him!”

Isn’t it crazy that after breaking up a year and half ago and not having spoken in over a year that you were still on my mind at such an important time in my life? You still had the ability to distract me and I’m mad at myself for allowing that to happen. I allowed you to take away a very small piece of my excitement. This well deserved career opportunity was slightly tainted by the mere thought that I may see you one day.

But the city IS big! What are the chances right?

So I tried to forget about you.

On my first day of work, I walked out of Penn Station excited and nervous as I headed to my new office.

I wasn’t thinking about you. I swear!

I headed east down 34th Street and stopped at a cross walk and waited for the light to change. I remember I looked down at the sidewalk. It was cold out and I was trying to shield my face from the wind.

And then I saw them. Brown shoes. Brown shoes that looked ridiculously similar to the brown shoes that you used to wear.

I forced myself to look up and there you were.

It was my first fucking day of work at my new job and you were standing right in front of me.

My heart stopped.

I couldn’t breathe.

Nausea took over.

I quickly pulled my hood over my head. If you turned around maybe you wouldn’t see me.

The light changed and we continued our walk. I was wearing heels and you were always a fast walker so before I knew it you were several sidewalk flags ahead of me.

I was safe.

But then the next block we hit another red light and once again you were standing only a few feet away from me.

Do you remember how my teeth chattered the first time we made love and you asked me if I was cold? And I told you that I wasn’t cold, that I was just nervous. Do you remember leaning down and kissing me to try to calm me?

My teeth were chattering as I stood on that sidewalk right behind you. I wasn’t cold.

Part of me prayed that you wouldn’t see me.

Part of me prayed that you would.

I don’t know how I would have acted if you saw me.

I don’t know how you would have acted if you saw me.

Would we have ignored each other?

Would our eyes have met and then would we have turned away from each other pretending we were just two random New Yorkers on our way to work?

Would we have had an uncomfortable conversation about…the weather?

Would you have smiled?

Would you have told me how great it was to see me?

I don’t know. I may never know.

But what I do know is that every fucking day I walk to work looking for your fucking shoes.

I am what you call a late bloomer.

I was 14 when I had my first boyfriend/kiss.

The summer before high school I was a counselor at a day camp and met Christopher. He only decided to be my boyfriend after my sister managed to convince him that dating me was a better idea than dating his ex-girlfriend again. Even at 14 I had dating problems.

I was 18 when I had my second boyfriend/kiss.

I waited nearly 2 years for my best friend Ryan to see me as more than a friend. After countless fights and crying over the fact that he didn’t want more than a friendship with me I invited Ryan to my prom, just as friends. He was my best friend and I didn’t want to go with anyone else. To this day I don’t know why Ryan changed his mind about me that night. But he did and we wound up dating the summer before I left for college. Ryan was my first love and my first heartbreak.

And then that was it on the boyfriend front. For a long, long, long time!

I thought college would be a new start for me. It wasn’t.

I had a few random hook-ups that never led anywhere. Oh and then there was Scott who really only loved my blow jobs, never me, and ended our casual relationship by dating my sorority sister. Ouch!

I graduated college and started working in the city where I met Will. We hung out on and off for over a year. I never thought I’d sleep with him. He just wasn’t the guy I had envisioned my first time being with.

But my 23rd birthday was fast approaching and I started getting anxious. I was still a virgin!!! Was this impressive? Did this mean I was a prude? Am I a total fucking loser that no one wants to have sex with?

I felt like I was running out of time. I felt that I was nearing the point where my conversations about my virginity would go from “Awesome! Good for you for waiting!” to “Really? What’s wrong with your vagina??!!”

For my birthday I met Will in the city and we decided to get a hotel room…

At the airport.

The Marriot Courtyard – JFK’s finest airport hotel was where my cherry got popped.

Will was far from my Jewish knight in shining armor I had been waiting for. But he made me feel sexy and loved and safe. He wanted me and he never put pressure on me to have sex with him. I was ready.

There were no candles. There were no flowers. There were no orgasms. Instead of music we had the sound of planes flying over our heads. He may have even paid for the room by the hour.

But even though my first time was far from what I had imagined or hoped for…I remember getting into my car and driving home with the biggest smile on face.

I wasn’t a virgin anymore.

I had no regrets that day.

I have no regrets today.

Back in September I went to a psychic for a reading. Don’t judge me!

Although he came highly recommended by my friend Marilyn, I was super nervous. Was I about to find out that I would die childless and alone?

Daniel the psychic immediately put me at ease and used tarot cards to read my future.

The reading was over an hour long but here are some of the highlights with my comments:

He immediately pointed out that the past two years were rough for me. I’m in the process of healing and once I do I will emerge more alive, lovely and fresh…a new me. I have been working hard and will need to continue to do so.

Found out my boyfriend of 3.5 years was cheating on me. Have been on countless horrendous online blind dates ever since and haven’t had a guy in my life for more than a month since the break-up. Yeah, the past 2 years have sucked Daniel..thanks for the reminder!!!

The emotional content in my life drains me. I go into the world projecting Marilyn Monroe but I’m more like Norma Jean, shy and vulnerable. I project power so that I am not taken advantage of.

For those of you who truly know me, you would know that this is a pretty accurate description. It’s exhausting….

October will be a big month for me. Nothing to fear but I would be making new choices.

I was offered a new job in October and accepted it.

I was right to let go of my past relationships. They weren’t the right guys for me.

Wait what? The alcoholic emotionally unavailable cheater wasn’t right for me???

2014 will not disappoint me. I will have true happiness and it will continue for the next 5 years. By 2015 I’ll know who the love of my life will be. This man will be a bit of a devil. I may get judgment from others and I will have to show them how great he is. He will love life and love me and want to be happy and bring a great smile to my life. I will have one daughter in 2016.

God I fucking hope so!!!!

I left the reading with exactly what I was looking for…a glimmer of hope.

I also left with a crystal that Daniel chose specifically for me. He gave me a chevron amethyst also known as the third eye crystal.

This crystal allows me to know more than I even know now. They have lines that run through them to allow for things to run smoothly in my life. The way I see things will continue to make sense and I won’t have a hard time making decisions.

Daniel told me to experiment with the crystal. He suggested I keep it in my bag when I go on a date.

Well…a handful of bad blind dates and then dating a much too thin barista with premature ejaculation for a month really made me question the amethyst and its magical love matching capabilities.

Fuck the bag…I’m just going to shove the amethyst up my vagina and see what happens!