Coffee with a Killer & Other Dating Stories

Once upon a time, I tried way too hard to find a husband.  I nearly got myself killed.

Before anyone was on Tinder or swiping left, I was single. For most of my adult life, my status had been single, party of one.  Emphasis on the party because I was a happy single woman.

Something changed on my 35th birthday. On that day, I woke up in a panic that I was never going to have a husband, a baby or a fabulous wedding. My biological clock began ticking with a vengeance. The beat of the tick and the tock was slow and the sound was like an extra heartbeat in my ear throughout the day. I was finding it hard to focus at work or sleep at night.

Milo and Tock from The Phantom Tollbooth 

My imagination manifested my biological clock into the form of Tock the Watchdog from my favorite book as a kid, The Phantom Tollbooth. Tock paced my floors giving me the brutal fertility stats of women over 35 and ratio reports of men to women in New York City.  Tock would jump up and down on my bed throwing pamphlets at me that had come in the mail from the “Freeze Your Eggs Clinic” and “Single Moms by Choice Association”.  All the pressure thrown at women my age rarely annoyed me, but today something was different. In every cliche, there is a dose of reality.  If I wanted to have a family one day, I had to take action now!  I went on a dating bender.

My 35th year on the planet, I went on approximately forty dates.  I was determined to meet someone.  I joined an online service, chatted up boys on airplanes, in grocery stores, at the post office, and wherever else I found them.  Meeting people was not my problem.  I met all kinds of men. I met a man that had an ostrich egg collection, a man that walked out of our date when he found out I hadn’t been to graduate school, a man that cried during dinner and a man that wrote me poems in Dr. Seuss like rhymes before and after our date.

My epic search was filled with great stories on a daily basis, I began taking notes.  

Bachelor Number 1 – The Cuddle Party Captain

The first guy I met online was a bit pervy.

The Cuddle Party Captain worked at a very popular morning show in New York City.  We had a very nice back and forth exchange online and a phone call that seemed above bar.  He was friendly, polite and smart.  There were no red lights illuminating on my warning system.

We decided to meet at a little wine bar a few train stops from my house.  The Captain didn’t look me in the eye as we shook hands. He was totally looking at my everything else. Gross! Next, he was all hands about helping me to my seat.

We both ordered a glass of wine and started chit chatting.  Somehow, we got onto the topic of movies and he revealed that The World According to Garp was his favorite movies and that John Lithgow’s transgender character was one of his favorite characters of all time.  Hmmm.  Maybe he is trying to let me know that he is a very progressive man or maybe he is in transition.  My warning lights were illuminated. First warning — touchy and skeevy while I am trying to sit down. Second Warning — Possible hidden message in story about loving Garp.

We had only been sitting for 12 minutes when he asked me, “Do you know what a Cuddle Party is?”  I answered, “No, I do not.”  When I heard the words Cuddle Party, I was immediately annoyed.  I had taken a shower and put on makeup for this.  He went on to tell me that he was a facilitator of the Cuddle Party Society. These were parties where men and women came in their pajamas and cuddled. He kept repeating, “They are NOT orgies.” Which to me was another way of saying, “They ARE orgies.”  My mind had drifted in discomfort when I heard him ask, “Do you think you would be interested in something like that?”  There was no waiver in his voice. His confidence in delivering the explanation and invitation amazed me.  “No. I do not,” I answered.  Suddenly, The Captain was pissed. “I really got the wrong idea about you,” he said with a tinge of anger.  “I thought you were a friendly southern belle with the open mind of an artist,” he continued. “Yes, you got the wrong idea,” I responded.  I paid for my drink, wished him the best and walked out.

Bachelor number 2 –  The Pegger

The second guy I met online was even more pervy.

The Pegger was an advertising executive.  Once again, we had great online conversations and one perfectly normal phone call. My warning system was idle.

The Pegger was really handsome.  He was very outgoing and knew a lot about wine and food.  Our date was off to a great start.  Once again, right about the 15 minute marker, things got crazy.  The Pegger asked me if I watched the show Weeds.  “Yes. I love it,” I answered. We discussed all the funny things that had happened on a recent episode.  Then he asked me, “Did you see the episode about pegging?”  “No,” I replied. “Do you know what pegging is?” he asked.  “No,” I answered. I was starting to feel deja vu.  He went on to explain to me what pegging is. Words were coming out of his mouth, but I only heard the sound of the emergency broadcast system in my head.  This wasn’t a test.  Pegging is when a woman wears a strap-on penis and has sex with a man up his keister.  This guy was asking me to peg him 15 minutes into our first date.  Why was this happening to me?  If he had the balls to bring this up 15 minutes in, it must be working some of the time. Suddenly, I felt sorry for women at large.  When the waiter came to take our order, I passed. I thanked The Pegger for the drinks and wished him luck with his search for a participant.

This was the second perv.  When I got home, I called for backup. I took counsel from my Gay Platonic Husband.  After telling him the story, he first asked me if I thought I could try pegging. “Who knows?” he said, “You might like it.”   We laughed ourselves silly for at least 100 seconds. “No thanks,” I answered. We kept discussing what I was doing to attract this.  We went over my online profile line by line and I saw it right there in black and white. ARTIST. Both of these men had really harped on the fact that I was an artist.  Female Artist must translate as sexually provocative and experimental in an online profile to a certain type of person.  I am not that type.  My policy on sex is that it’s one of the most fun things life has to offer between 2 consenting adults. I appreciate the guts it took for these two men to let their freak flags fly right away. Giving me this information so quickly on our 1st dates saved time.  I hope they appreciated my flag that I waved right back at them.  My flag said, “Dude must like having sex with one woman that doesn’t require third parties or false appendages.” As far as the online dating world was concerned, I was a small business owner.  I NEVER referred to myself as an artist when talking to prospective men from that day forward.

Bachelor number 3 – Chief Buzz Kill

Chief Buzz Kill was a victim of New York Toxic Work Culture personified.  He was a top executive at one of the biggest companies in the world.  He worked a minimum of twelve hours a day every weekday and pretty much weekends too.  He was such a workaholic that I am not really sure how the planets aligned and we stood next to each other in my favorite neighborhood bar.  Somehow, I got a date.

The main selling point for CBK was his looks.  Sure he was rich, successful and ridiculously smart, but that paled in comparison to his looks.  He is absolutely one of the best looking men I have ever seen.  He was a tall ex-athlete with beautiful curly hair and brown puppy dog eyes. Think boyish American Clive Owen. In hindsight, his looks were the only thing I liked about him.  As I got to know him, he was a total bummer.  I stuck with it for purely shallow reasons.  Plus, in Manhattan, where the women outnumber the men, someone good looking, straight, and a non-perv can be really appealing for a certain amount of time, even if they have nothing else to offer.

One of the main challenges I faced with CBK was his schedule.  He went to bed at 10 p.m. no matter what and I mean no matter what. This lights out curfew made dates stressful for me.  I felt like I was on the clock.  He doesn’t get off work until 7 or 8, which meant if I wanted to get to know him at all or have any romance whatsoever, dinner had to be quick or we needed to just skip it all together. CBK also got up every morning at 5:30. His schedule was exhausting.  He never loosened up.  I don’t think I ever saw this man relaxed.  

The more I got to know CBK, I discovered that he was ridiculously anal and critical about everything.  He was really not happy with much in life.  He didn’t like comedy, T.V., children, parties or Christmas.  Let me say that again, this man didn’t like Christmas. Not liking Christmas was a problem for me.  I LOVE Christmas.  It wasn’t like he was another religion and happily celebrated other traditions. He just didn’t like fun.  No matter what I tried, I just couldn’t get him to have any kind of fun.  The only things I could confirm that he really liked were feeling superior to others, stress and concentrating on how hard life is every single freaking day.

It was only a matter of time before he turned his negativity and critical eye on me.  He told me that he hated my favorite painting and went on and on about it.  CBK complained that I made decisions too quickly and that it annoyed him how social I was.  At first, his slams hurt my feelings.  Eventually, I realized that this is what happens when happy people date killjoys.  It might work at first because both parties are intrigued by the oppositeness of the other, but eventually the killjoy is going to get that gun out and try to kill your joy.     

One day, he announced to me that he was becoming a vegan.  I thought he was kidding because he was a real meat and potatoes kind of guy.  He wasn’t kidding.  When I asked why, he said, “Just to see if I can do it.”  There is nothing wrong with being vegan.  In fact, I think it’s a very healthy style of eating. However, doing it just to see if you can seemed absurd. 

One beautiful summer night, we met for dinner at a popular upper west side restaurant famous for outdoor dining.  Forever the optimist, I was really looking forward to a great meal, a glass of champagne and maybe, if I’m lucky, a little romance.  The waiter comes to our table.  I ordered the fish which sounded fabulous and a glass of champagne, my favorite.  Then his turn, “I will have an order of steamed broccoli and a cup of decaf coffee”, he said.  The waiter just stood there for a few minutes with his pencil in his hand and then said, “Is that all?”  “Yes” CBK confirmed.  “Have you already eaten?” I asked.  “No, I am just following my vegan diet,” he replied.  When he told me this, I suddenly felt like the luckiest woman in the world knowing that I was never going to be married to this person.

The comedy began as our dinner headed toward the table.  The porters, who totally did not speak a word of English, were on their way.  I could already see what was about to happen.  Who do you think they just knew that order of steamed broccoli was for?  The porters tried so hard to deliver that broccoli to me.  There was really just no telling them that it was actually for the man at the table.  I eventually informed them via persistent sign language that it was for my boring ass date.  There was an older couple sitting just across from us laughing who witnessed the entire thing. I found it comforting that at least my feelings were echoed by someone next to the situation.  I ate my fish and sipped my champagne fighting laughter at first and then I became sad.  I knew this was our last dinner together and in fact it was.  

Bachelor number 4 – The Perfect Candidate that Did Not Fog My Glasses

The Perfect Candidate that Did Not Fog My Glasses tested me in a new way. He was a friend of someone in my social circle.  PCTDNFMG was totally nice, polite, gainfully employed, cute, happy with his life and emotionally healthy.  There was nothing wrong with him.  He called when he said he would call.  He did everything a man courting you should do – seriously.  It was so refreshing to meet someone with all the makings of a nice mate.

PCTDNFMG opened doors and refused to let me pay for anything.  He discussed marriage and children openly without freaking out.  He even started every date by telling me how great I looked. I once mentioned how much I loved Hydrangea and he had an arrangement messengered to me the following morning.  After our first few dates, I was a bit concerned that I didn’t feel any chemistry.  My mother and all of my married friends told me to give it a few more tries. Maybe he would grow on me.  

PCTDNFMG was very cute. He had piercing green eyes and a great smile. Women can easily fall for a guy based on many factors.  I am a strong believer that personality can make a guy sexy as hell once you get to know him.  I just knew that this was going to happen for me in this case.  

I kept going out with him.  We had great conversations and I really felt comfortable with him.  I have to say as a person, he is awesome. I loved him as a person.  We became great friends and true love is just friendship on fire right?

Eventually,  I started dreading the end of dates and that he might try to kiss me. However, I wasn’t ready to give up because this guy would make someone a great husband.  I was having a hard time accepting that the someone wasn’t me.  I kept trying.

On about date six, it became very clear that I needed to jump ship because I didn’t want to jump him.  We were having dinner and he had just come from work.  He was dressed in the typical New York male corporate uniform; white button down, tie loosened post day, and suit pants.  He was telling me about his day and I couldn’t help but notice a tuft of hair sticking out the top of his undershirt.  It was black and curly and I swear it was waving at me.  It wasn’t attractive nor unattractive.  It was just there and it whispered to me, “Cut the cord! Set him free!”  It was selfish of me to keep seeing this guy, when his perfect wife was out there somewhere.  So I let him go.

Bachelor number 5 –The Porn Star

The Porn Star was a set up.  I must start the story with telling you that The Porn Star was a closet porn star.  His beard career was fitness trainer slash actor. He worked at one of the very exclusive and expensive fitness clubs that elite Manhattanites who are ridiculously rich and in shape go to.  My Gay Platonic Husband had picked him out for me at his gym one day and invited him to one of my parties so I could meet him.  My GPH had explained that this guy was hot, definitely straight, and single.  

When The Porn Star entered my front door, I was impressed.  He was carrying a silver tray of chocolate covered strawberries that he had made himself.  They were gorgeous and so was he.  He was perfectly sculpted and bald. He looked exactly like the actor Billy Zane.  I immediately noticed something very sexual about him.  He was the kind of guy that looks you straight in the eye in a way that weakens your knees. When he grazed his hand on the small of my back, I felt it all over my body.  

I didn’t get to talk to him that much at the party.  When I asked about what he did, fitness trainer slash actor was his answer.  He had been in many plays and a few movies and was a typical struggling New York artist waiting for his break. Then The Porn Star mentioned where he lived,  “I own a two-bedroom apartment on the park just a few blocks from here.”  I remember thinking that he must be independently wealthy because any apartment on the park in any direction of my house would cost millions of dollars.  I wasn’t sure where that kind of money would be coming from. I just passed it off as inheritance, which is often the case in New York.

As he was leaving the party, I stepped out in the hallway to give him a proper send off.  He was all over me and trying to kiss me.  It was electrifying.  This guy was definitely a professional, although I had no idea to what magnitude.  He asked for my number and walked into the night.

The next morning, I was talking to my BFF from childhood reviewing the details of my party and everyone who had attended.  I told her about The Porn Star.  “He’s an actor?” she asked.  “Yes,” I replied.  “Give me his name and I will look him up in a few databases,” She said.   BFF was also an actor and knew the skinny on all the sites to look up anyone and everyone who has ever been in a movie.  

She started the search. “Hmmm,” she said. She took a brief pause and then shouted,  “OH MY GOD! Don’t get too excited, this might not be him.”  “What? What?  You are killing me over here,” I return shouted into the phone. “Let me just read you a few titles” she said “Erotic Adventures of Eddie the Pool Boy, Eddie the Pool Boy II and Sexy Serenade.”  “Maybe he didn’t have a major role and just needed to make some money,” I rationalized. “Nope,” she said, “he is the star of most of these.”  Holy guacamole!  This was interesting.  

We discussed frantically that this could totally be some other guy with the same name.  Of course, there were no pictures of him on the site.  That would have been too easy.  The only thing we could do was go get one of the movies and confirm whether or not it was him.  My brain was spinning.  This would explain where the money came from for the multi – million dollar apartment on the park.  It would also explain the electric sexual current leaking from his body at all times.  BFF started laughing so hard and I asked her what was so funny. “He brought chocolate covered strawberries to your party.  That is the most hilarious “9 ½ Weeks” porn cliché I have ever heard of.  This has got to be him,” she said.  We agreed that I would do some investigation and get back to her as soon as possible.

I called my PGH and quickly got him up to speed.  He completely thought that we were ridiculous and we shouldn’t believe everything we read on the internet.  But I could hear it in his voice, behind his confident, mature statements; he was curious as hell what I was going to find.

I headed out to a sex shop in my neighborhood.  There are actually two on the upper west side that I could think of right away.  I have passed them hundreds of times and never had a reason to go in.  I now had my reason.  

“Hi,” I said to the porn clerk.  “Yeah,” he said flatly like I disturbed him from something important.  I was thrilled to be able to ask the next question.  There was something totally fun about this.  “Do you have The Erotic Adventures of Eddie the Pool Boy?” I delivered with confidence.  As the porn clerk looked on his computer, I glanced around the store.  I was surrounded by walls of porn videos, cheap lingerie with leather and feathers, dildos in every color, handcuffs and an entire wall of every kind of lube and condom you could think of.  It was making me giggle until I saw this creepy man skulking around in the corner.  Suddenly, everything had a different context and I wanted to get out of there.

“I have The Erotic Adventures of Eddie the Pool Boy,” he said, “do you want it?”  “How much is it?” I asked. “$29.95,” the porn clerk responded.  “I’ll take it,” I said.  I paid as fast as I could and with cash.  I didn’t want there to be a record of my being in this establishment.

Once out of the store, I shed the feelings of disgust and the fun feeling of discovery returned.  I quickly called my GPH and told him to meet me at my house in 15 minutes.  Second call was to BFF to inform her that I had the video in hand.

On pins and needles, my GPH and I sat on the couch as I pressed play.  This was already hilarious.  The first scene begins and out comes The Porn Star.  It was he.  We squealed with sustained laughter for a good 120 seconds. We were mesmerized as The Porn Star seduces the rich Beverly Hills lady who hired him to clean her pool.  We couldn’t stop laugh-squealing.  The worst part was that The Porn Star was so good that my GPH and I started rationalizing if there were some way I could just deal with the fact that he was a porn star for a few dates so I could take him for a test ride.  “Could be the best 20 minutes of your life,” my GPH said.  Tempting as it was to have that on the trophy stand, I just couldn’t deal with it.

I never had to face the moral dilemma of going out with The Porn Star.  I think someone upstairs was watching out for me. As it turns out, HE NEVER EVEN CALLED.


Bachelor number 6 – The Murderer

How does one almost get killed looking for a husband?  I saved this one for last. It’s not a funny story.

I met The Murderer at Zabars (a gourmet grocery store on the Upper West Side).  The conversation started as a result of his dog sticking his head into my grocery bag.  He had this huge white wolf looking dog.  I froze when the dog put his head into my bag because I am scared to death of big dogs.  The Murderer was on his cell phone and it took him several seconds before he realized what was happening.  “I’m so sorry,” he said, “Did he eat anything?”   “No, it’s ok. I am just afraid of dogs,” I said.   The Murderer was tall, good looking and very cocky as he asked me if he could call me.  I have to say that I did not get any scary vibes from him, just the dog.

He called a week later and asked me out for a coffee.  I still didn’t notice anything strange.  On the day of our coffee date he called to firm things up and this was the first time I noticed something weird.  He asked me why I had a block on private numbers on my phone and he sounded almost angry about it.  I told him that I had had a lot of solicitation calls due to my business and he seemed to be ok with the answer. There was something weird about his reaction to it. In retrospect, this was the first warning.

We met at Starbucks in our neighborhood; he didn’t live far from me.  He was full of himself as I had originally thought and told stories about how he grew up in the city and how he used to hang out with Andy Warhol and Keith Haring when he was in high school.  A lot of things were running through my mind: this dude was completely unsupervised as a teen, possibly lying or maybe he was trying to impress me with this because I’m an artist?  In his next few sentences, he revealed that he was an alcoholic and had several major incidents in his life that were a result of his abuse of alcohol: fired from a job, stole a marble bust from the Metropolitan Museum of Art, broke up many girlfriends, arrested, lost a lot of money.

I had heard enough and I told him that I was going to meet my girlfriends out for drinks.  As we said goodbye, he touched my hand.  When he did, I got a chill down my spine and not a good one.  My hand recoiled immediately involuntarily.  My sixth sense kicked in and I knew this guy’s elevator wasn’t stopping on all floors.  We left and that was basically it.  I didn’t hear from him again.

Six months later I was out with a group of friends on a Saturday night and I see him on the street with one of his friends.  As we got closer, The Murderer put on his sunglasses (it was 9 p.m.).  We could tell that he was drunk.  Since he had confided in me that he was an alcoholic, I knew there must be trouble.  The Murderer’s friend seemed visibly uncomfortable with the fact that our group was speaking to them.

The Murderer was really friendly like only a drunk can be. He was hugging on me and saying my name too loudly.  I saw out the corner of my eye that my friend JN looked worried like he might have to defend me. I kept it short and we walked away quickly.  

“Laura, how do you know that creep?” JN asked.  “I went on a date with him a few months ago,” I said.  Another friend of mine, M&M, was out with us.  M&M has an incredible capacity to notice detail and I am pretty sure she has a photographic memory. She noticed that he had a black eye under his glasses and appeared to have been in some kind of fight.  It was just weird all the way around.

The following Tuesday, I awoke to the sound of my phone ringing at 8:00 a.m.  My answering machine picked up and M&M started speaking frantically, “Laura, get up and go get The New York Post. That guy from Saturday night is on the front cover and he has murdered his girlfriend.” M&M reads every paper before 9:00 a.m.  I jumped up and picked up the phone.  “What?” I asked.  “Go get the paper. I am on the way to a meeting. I will call you back later.  I can’t believe this,” and she hung up.

So many thoughts were going through my mind.  As the story of the murder unfolded in the papers and on television, I just couldn’t believe it.  It was horrible and had happened the day after we saw him.  It was hard for me to digest that I had met this guy.  I was overwhelmed with sadness for this girl and her family.  I felt incredibly lucky that this had not happened to me.  I fielded calls for most of the day because by 10:00 a.m., everyone in The Loving Network had heard about it and was calling me to check in.

Meeting The Murderer made me realize that I needed to develop some serious filters for my dating life.

I made a list of questions.  From that day forward, I asked each and every one of these questions prior to a first date if I met the person online and on a first date if I had met the person in real life or through a friend.

The Laura Loving Safety Quiz

    1. Have you ever been arrested?  More men that you think have been arrested at some point in their lives.  Sit back and listen to the story.  You can learn a lot.
    2. What is your current legal marital status?  I could tell every single time someone was lying and shocked when a few just came right out and said they were married.
    3. Listen when someone tells you who they are and believe them. If a guy even jokes about something dark, super kinky, illegal etc, they are testing the water with you.  Next!
    4. What is your relationship with drugs and alcohol?
    5. What are your views on intimacy aka SEX? After the Pegger and The Cuddle Party Captain, I had the guts to ask this question right up front.  I wasn’t looking for a pegging partner so I needed to be real about what I wanted.
    6. Do you see yourself as a parent within the next 5 years of your life. This question always scared away exactly whom I needed it to.

After implementing this simple test prior to dates, I started to meet men more in my peer group.

My 40 dates at 35 made it obvious that I could not make love happen.  I wasn’t sorry for putting it out there and I actually enjoyed each and every adventure.  The experience made me more confident that my life was great  without a partner.

I had thought that something was missing.  Nothing was missing.  My life was already in full swing and the good news was that I was happy and surrounded with love.  Maybe not the kind where you put on a white dress, but love all the same.  



New York artist most known for her Lady Liberty art prints and original paintings. Discover Laura's complete I Love New York series in the shop.