Monthly Archives: September 2014

D8 with 1996

New York, as well as the rest of the world, is celebrating Derek Jeter this week. From his Gatorade commercial to #2 Yankee jerseys everywhere you look, the streets of Manhattan are paved in Jeter. It seems only yesterday was 1996 and he was being honored as the VIP Rookie of the Year.

It got me to thinking about other milestones of 1996. Betty Rubble was finally immortalized in a bottle of Flintstone Chewables. One of my favorite Miss USA titleholders, Ali Landry, won the Miss Universe evening gown preliminary, but lost on the big night to a super charming, hair flipping and surgically enhanced Miss Venezuela. Charles divorced Diana, and I ended my first of three major relationships.

In 1996, the New York Yankees gave us #2, but I had my own #2 that year as well. I decided to take the advice of the new Miss Universe, who when asked what she was going to do after winning, gave the answer “Eat! Eat! Eat!”. It had been a long time since I had a meal of flirtation, connection and love, so I immediately got back into the dating saddle post-breakup.

My 1996 #2 man was Mark. I met him three days after my break-up. My Ex’s father insisted I take his season tickets to the Boston Symphony, so I grabbed my best friend and went to Carnegie Hall that early Autumn evening. At intermission, I noticed a very handsome man in a blue Brooks Brothers suit checking me out. He started a conversation. We met after the concert and had a drink. We had dinner the next three evenings.

It was official- I had just found my first Transition Man.

I dated Mark for what was an amazing six months. As amazing as it was, there were simply too many issues that would render this relationship a short story and not a full-length play. We mutually ended it. I’d like to think our story was like a Barry Manilow song from fifteen years prior; we simply had the right love at the wrong time. At the time I was angry, as was he. And at the time, Mark knew it had to end in spite of not wanting it to end, as did I. There were just so many, many reasons why it would never, ever work out.

As New York and the world continued to celebrate the storybook ending of Derek Jeter’s career, the most impossible and frankly miraculous thing happened on an early Autumn evening in my world- I ran into Mark.

We had a drink, and enjoyed a conversation. Lots happened in eighteen years- good and bad. We both experienced a broken heart more than once. We experienced loss, and we experienced some major successes. With eighteen years of age on us, the anger of the past melted away, and the focus on the positives of our past relationship was forefront. Mark said that he thought of me often, as I of him. He acknowledged that he had gained a few pounds since his marathon days in the ‘90s, and I told him he was still a handsome devil. He then said something and did something that took me back to 1996 faster than the YouTube video of Jeter’s single in Game Six of the World Series that brought the score to 2-0 over the Braves.

“You look better now than you did then, and you looked great then. Your chest is still up! I always loved your chest!” he said smiling as he leaned in and gave me a kiss. With that, our 1FineD8 was over, but 1996 lingered in my head and put a spring in my step for the rest of the night.


Cher sang that she would turn back time IF she could find a way. Cher was well aware of the fact that there is that is no way. Eighteen years lost is exactly that. It would be simple to dwell on the loss of what could have been the relationship of a lifetime, but what my 1FineD8 with Mark reminded me of was the gift he gave me in 1996- a gift better than any World Series Pennant. Mark was the 1996 MVP of showing me that I still had it.

A good Transition Man serves as a distraction from the mess you left behind, but a great Transition Man is like an alarm clock- he will awaken you to all the great attributes you possess that your last relationship caused you to doubt.

The 2014 version of Mark may have earned a few lines on his brow and gained a few pounds in his midsection, but the sparkle in his eyes- that 1996 sparkle when I walked into a restaurant or to his office to meet him- remained unchanged. I wasn’t on a quest for any reminders or validation, nor do I really require that regarding my attributes, but I admit it was a really nice feeling to get one. Even the most confident people benefit from a reminder that someone out there thinks they are just the greatest.

If you ever have an opportunity to grab a beer with a former fineD8 from years ago, I recommend it. Enjoy the time travel, and enjoy the memories. Keep in mind, Derek Jeter isn’t going to win an MVP Rookie Award again, Alicia Machado will not win Miss Universe again, and Betty Rubble will never again debut in a bottle of Flintstone Chewables. You won’t go back to what you had. Whatever you end up with, be it a friendship, a new beginning or simply a moment of reconnection honoring what you once had, you really can’t go wrong.

D8 without the Spectacles

I love a good coffee date with a great friend, and when that great friend is Dateologist Tracey Steinberg, the coffee date is destined to be a great one! Midway through our time together, Tracey asked how my dating life has been going. I filled her in on a situation that is straight out of her incredible book, Flirt for Fun & Meet the One- Dating Secrets from the Dateologist.

In Tracey’s book and in her Flirting Parties, she suggests that when in a social scenario and you want to meet new people, using the environment to find a topic for conversation is a great way to approach someone you’re interested in meeting. I explained to Tracey that I inadvertently changed the environment of a social setting by doing something as simple as taking my glasses off. Within minutes, a cute guy approached saying, “You took your glasses off!”, starting a conversation that ended with a request for a date. Tracey asked me to take my glasses off, and stared at me. She then asked me to put them back on, and to take them off again. My dear friend and very smart Dateologist suggested I try ditching the spectacles the next time I go out. Tracey suggested I shake up my look and let the men of Manhattan see my eyes, not see a pair of Ray Ban bifocals.

Tracey has never led me astray, so that is exactly what I promised to do- glasses off and in the pocket on my next excursion. And that’s what came to pass three days later. I specifically wore a button-down with a left breast pocket that would accommodate my spectacles. I was easily able to see people, but did run into a bit of squinting when discerning a twenty from a ten when purchasing my first Heineken. As I walked around the bar, I noticed that I was getting a lot of looks. I smiled at a few of the guys, and the next thing I knew one was talking to me, followed by another. Others walked by, and definitely checked me out.

Seems Tracey was right- men make passes at men who don’t wear glasses!

At a moment when I was alone, I noticed a man that was incredibly handsome. He was an interesting combination of the dangerous bad boy edge of Jack Nicholson with the debonair look of Robert Wagner circa Heart to Heart. Anyone who knows me well knows that combination is definitely a flavor that holds my interest. A man who was talking with my bad boy dreamboat motioned me over to ask my opinion on a topic, and that’s how I met Max. Within a short amount of time, Max and I pulled away from the conversation and focused on just us. Lots in common, lots of laughs, and three hours later we made plans to meet for dinner the next week.

Tracey was right- taking off my glasses helped others to see me. We’ll see what happens with Max, but I believe he has 1FineD8 potential. If we brought it to a vote, I believe the “eyes” would have it no other way!



Applying Tracey Steinberg’s feedback proved to be a very smart move on my part. Not everyone gets to have coffee with this groovy and smart Dateologist, so I highly suggest visiting to learn more about her. I also suggest getting her book, Flirt for Fun & Meet the One- Dating Secrets from the Dateologist. It’s available on, and can be found at:

Sometimes you need to change up your look to attract a potential 1FineD8. I love my glasses like I love my coffee, black and bold, but sometimes people take their coffee differently. Sometimes they don’t even like coffee (which for me is so hard to believe!). Like Starbucks, changing the focus of the menu, sometimes featuring the pumpkin bread instead of the dark drip, helps the “consumer” see the many facets of your brand. One of the first things Max said to me was that he thought my eyes were amazing. I sincerely don’t believe that Max saying that to me sans spectacles was a sign of him being shallow- he would have said the same thing to me if the glasses were out of my pocket and resting comfortably on the bridge of my nose.

When you plan to go out with friends or by yourself to cultivate a prospective 1FineD8, switch up your look once in a while. It’s difficult to explain, but doing this will also flip a switch in your mind, and your carriage will improve and your mindset might actually be more confident. Both were proven true for me in this experiment. If you’re a pants gal, try a cute skirt with killer boots. Guys might want to consider khakis and loafers as opposed to denim and sneakers. And for all of us four-eyed daters, consider taking those glasses off. You might just have the best night ever- one that’s mind blowing to the Max!

D8 with the Needy Octopus

When Tom called to confirm our coffee date, he asked one last question that in retrospect should have raised my eyebrow…

“What are your thoughts on PDA?”

Public Displays of Affection, as I told Tom, were fine. A little hand holding while walking down the street is totally in bounds. A simple kiss after a first date is appropriate. I told Tom that when PDA inspires public feedback of “Get a room!” you know you’ve gone too far.

I really didn’t think much about his question, but within five minutes of our date PDA reared it’s head. As I sat down with my Venti Dark Roast, Tom leaned forward and started rubbing my arm.

“Wow- you are so gorgeous! Even better in person!” exclaimed Tom, as his hands left my arm and went straight to my knee.

“Thank you- so are you.” I responded. Even though I was a little dumbfounded that he was now rubbing my leg, my response was totally true. Tom was 6’4”, mid 40’s and definitely no stranger to the gym. He’s a player in a rugby league- enough said.

As our conversation continued, Tom made it clear that he really wants a relationship. He’s been single for three years, and doesn’t want to be alone. He told me about a health scare he had recently experienced, and he had to face it by himself. He was tired of being a solo act. All the while explaining this, Tom’s hand never once left my body. An arm, an ankle, a knee… if the NYPD dusted me for prints I’d look like a sloppy crime scene. I knew I had to address this, and I did it the best way I knew… I made a joke.

“You know, Tom, I’m starting to feel like one of those radio contests that if you take your hand off me you’ll lose the chance to win the keys to a new Ford Explorer.”

“Oh, I’m sorry. Too much too soon… but I really like you.”

“And I like you too, but let’s get to know each other.” I said.

Tom seemed to be very cool with that, and for the first time on our date I wasn’t being petted like a dog. Unfortunately, this didn’t last long. Tom repositioned himself on the banquette we were sitting on, asking me to lean in on him as we talked.

“Tom, I’m drinking hot coffee, and we’re not at home. No.”, was my response. Feeling a bit deflated, Tom sat up and grabbed my hand and continued the conversation.

I ended the date soon after, thanking him for meeting me and telling him that it was nice to get to know him. He came in to give me a kiss, and of course in true Tom fashion took it upon himself to recreate From Here to Eternity’s beach scene, throwing me against my car and planting one on me like the Japanese bombers were minutes away.

Twenty minutes after I got home, Tom called. He wanted to thank me for the date, and to see if I’d go out with him the next day. At this point, I thanked him and told him that the chemistry just wasn’t there to warrant a second date. I wished him luck on his own quest for 1FineD8.


I did some reading about the mating rituals of the octopus, and learned that my date was more of an octopus than he knows. Besides being all hands, what Tom wanted more than anything was a relationship. Tom was in love with the idea of a permanent relationship- so much so that getting to know a potential mate wasn’t all that important (that would come in time, once the relationship was well under way). I learned that in some species of octopi, the male actually severs his “mating arm” and gives it to his partner to allow her to reproduce at her discretion and to her scheduling needs. Like such octopi, Tom would have cut his own arm off to have that relationship.

As if the concept of “instant relationship” wasn’t unattractive enough, the excessive PDA was just way too much to handle. It was so over the top that it distracted me from getting to know anything about Tom. I’m sure there’s a really great guy somewhere in there, but the desperation of having a relationship compounded with the groping made that discovery impossible.

When on a first date, keep in mind that nobody wants to date an octopus. It’s ok to look, but spend the time getting to know your date and save the touching for a future date. Most daters have their eyes on their endgame, which is a relationship. Wearing your endgame on your sleeve on a first date is going to pressure the individual sitting across from you, which is the last thing you want to do.

D8 with Martha Dumptruck’s Brother

I decided to give J-Date a whirl. Oy.

There are lots of cute Jewish men looking for relationships, and my profile caught the eye of one man in particular. David was very cute. Originally from Los Angeles, he was a partner in a downtown law firm and a New York resident for the last twenty years. We had a very fun online chat, and he closed a date with me almost instantly.

We decided to meet at the fountain at Lincoln Center, and from there would go to PJ Clark’s for drinks and nibbly bits. When I spotted David, he was every bit as handsome as in his pictures. He fibbed about his height (definitely 5’6”, not 5’8”) but in all the physical package was quite good.

After being seated at a great table, David admitted that he took a look at (which is fine as I tell all my dates about this blog and it’s mission). That said, David proceeded to ask me a very interesting, yet inappropriate first date question…

“As a relationship expert, I’d love to get your take on my last two breakups, ok?”

As we all know- or should know- discussing past relationships on a first date is a major dating sin. The first date is about moving forward on a road that hopefully leads to a connection. It’s not meant to be a forum to perform an autopsy on relationships past.

“Well, David, a first date really isn’t meant to discuss past boyfriends,” I responded.

“Indulge me, handsome… just for a moment,” replied David, flashing his sparkly and very convincing smile.

I indulged, giving David his moment. His moment lasted 90 minutes. Here’s a brief synopsis of what came out when he backed up the dump truck and poured the contents of his failed romantic past all over my 1FineD8…

Dump Truck

“I’ve had two relationships. My last relationship was an open relationship, and after two years he found someone better and dumped me. That really hurt, almost more so than my first relationship’s ending. My first and I were together for ten years- open relationship. I was in Cleveland a lot for work, and I developed a relationship with a man there, which lasted almost a year. Well… the Cleveland guy came to NYC and I introduced my partner to him (he knew all about him). Long story short, they really hit it off and now they’re together living in Cleveland.”

“Your partner dumped you for your boyfriend?” was the only response I could give.

“Yes. I was really surprised, but not surprised. It really hurt. Now I’m dating again and dating makes me anxious. I believe dating is just a shopping excursion for someone that is destined to disappoint me and eventually leave me for someone better.”

At this point, my wine glass was on its second fill and close to requiring a third. I decided to wrap ip this therapy session… I mean first date.

“Well, David, it seems the commonality between the two would be that your relationships were open. Maybe that is something you don’t want to repeat in your next go. Would you consider having a monogamous relationship?”

“No. I want to keep my options open.”

“In that case, it seems like your two Exs also kept their options open, and they chose to exercise their escape clause. They just beat you to it.”

“That’s true.”

“Maybe you need to meet the guy that going to make you want to seal the deal- the man that brings you so much joy, so much of a connection that you only want him. You say that you’re afraid that a potential partner will leave you for something better. Maybe if you focus on just one man and enjoy that process, it will bring out the best David possible. The David that he’s never ever going to want to leave.”

“That sounds like a lot of work, Craig.”

And with that, I asked for the check.

First dates are meant for two people to get to know each other. First dates paint a picture of how you communicate, how you laugh together and if there is a spark of chemistry that leads to a repeat performance. Bringing up past breakups casts a negative cloud over this initial meeting, in my opinion. The cardinal rule to follow when it comes to a first date is that all modes of transportation are in bounds for conversational topics, with the exception dump trucks and moving vans. Discussing your Ex is about as sexy as planning cohabitation before your waiter can even offer you a dessert menu.

On my date with David, I basically witnessed an autopsy of two failed relationships and was asked to give my opinion on the findings. It wasn’t the question of open vs. monogamous relationships that was a deal breaker for me (frankly it’s not really debatable because what works for some couples may not work for others and is really a decision to be made and judged by the two in the relationship) but the fact that I really didn’t get an opportunity to learn what made David tick. I didn’t get to see if we had anything in common, and there was certainly no opportunity to see if there was a spark. What I did learn, however, was that David was still stuck in the drivers’ seat of the dump truck containing his past romantic relationships. He was so not ready to move on to a new relationship. I was concerned to hear his negative views of dating as a portal to ultimate disappointment, and the major red flag was when he balked at the concept of working at a relationship.

Definitely not 1FineD8.

D8 with a Suitcase and a Stopwatch

I received a message from a very handsome man via a gay social networking application. It was a simple “Hi, how are you?” that started the ball rolling between this gorgeous man and me. We talked about our families, our careers, and our dogs. He gave me a hard time for not liking mustard and I loved the fact that he’s no stranger to making his own ice cream.

We made plans to meet the following night, in spite of one thing about this man that I’ll get to later…

The following night became the night of my first date with Jeffrey. He was even more gorgeous than his photos. Tall and burly with salt and pepper hair and a trimmed beard to match, Jeffrey embodied a level of sophistication and confidence impeccably wrapped in the looks of a model straight from the Cabela’s catalogue. Our eyes met, we both smiled ear-to-ear smiles, and before I knew it, Jeffrey planted one right on me without saying one word.

After I caught my breath, I knew that starting a date with Jeffrey in reverse and getting the first kiss out of the way at the beginning was the only way to begin an experience dating this man. The next five hours were spent laughing, talking, and really getting to know each other. There were quiet moments where we just stared into each other’s eyes, and not one moment was an awkward silence. The entire evening flowed, and with each glance and every laugh, the connection we felt was undeniable. Jeffrey was like a tall glass of refreshing iced coffee after an hour of mowing the lawn on a 90-degree afternoon.

But… My1FineD8 was a resident of Washington, DC and was here on business.

I knew that going on a date with a man carrying a suitcase was not the smartest thing to do. I thought there could be no harm in meeting him and possibly making a new friend. Considering that my last few dates didn’t result in any deep connection, I saw no harm in meeting him for coffee. What I didn’t think about was what would happen if we really connected. In the case of this man with a suitcase, we connected to a point where I can safely say that it was one of the deepest connections I’ve ever experienced.

Which brings us to the stopwatch. I knew time was ticking with each laugh and each smile. This fine date would come to an end, and for the first time in a very long time, I wasn’t ready for it to end. Luckily Jeffrey was of the same opinion. Unlike my other dates, I could simply close the deal on a second date. But with the distance thing, I knew that would be impossible this time. Jeffrey, on the other hand, was of a totally different mindset.

“What are you doing Friday night?”
“Ummm… wishing I was in Washington?”
“I think I’m going to change my return trip and take you out Friday night.”

Which is what came to pass. My 1FineD8 with Jeffrey turned into two fine dates. Two extraordinarily fine dates. Yes, the suitcase and stopwatch were there, but I did my best not to think about them. Jeffrey made is super easy to forget about them, and his changing his return trip just to have a date with me was probably one of the most considerate things I’ve experienced in quite a while. In spite of the stopwatch, every minute with this incredible guy made the last seconds of our second date not so sad.

When I said goodbye to Jeffrey, I knew there would be a third date… and a fourth, and a fifth too.


One hazard to online dating is meeting a potential 1FineD8 that isn’t exactly zip code friendly. You may set your profile to only search for potential dates within a close mileage range, but there is nothing stopping someone else that has chosen an expanded reach that happens to read… and like your profile.

It would have been very easy for me to dismiss Jeffrey based on zip code alone. There was no investment of time, no drinks purchased, and definitely no emotional tie. But there was something special about him- a spark that has been lacking in a lot of the dates I’ve experienced. I threw caution to the wind and gave into the hunch that he was as great of a man as he appeared in his pictures. Fortunately, my hunch was right.

And unfortunately, my hunch was right. Unfortunate because of a zip code. Unfortunate because it presents a challenge that most daters don’t have to face, which is getting to know each other via phone and text while most couples get to date the conventional way. Dating in this manner is not what I envisioned for myself, as I’m confident Jeffrey would agree. I am also confident that Jeffrey would agree that if our biggest unfortunate is a zip code and a ride on Acela, we’re pretty damned fortunate.

My advice to you is to follow your gut when it comes to getting involved with a potential date that may not be geographically convenient. If you feel the distance is going to present a hardship, then by no means go on the date. If you look at the distance as secondary to the person that is asking you out, then go for it.