Monthly Archives: October 2014

D8 with Two Dicks

Elizabeth Taylor married Dick twice. Samantha Stevens had one Darrin, but Elizabeth Montgomery worked with the two Dicks that played him. Even the 2014 Stanley Cup Final had two opposing Forwards, both were Richards. Without trying, I too had a date with Dick… and a date with Dick.

Let’s start with the second Dick and work our way back to the first…

Dick was a very nice man I met online. We chatted for a couple days, and planned a date for the weekend. Seeing that Dick was New Jersey based, I suggested we grab a glass of wine at Ferraro’s in Westfield, which is a great Italian restaurant with really good food. Dick was adamantly against Ferraro’s and anything in Westfield.

“Can’t do Westfield- my Ex lives there, and I don’t want us running into him,” explained Dick, who seemed to be very nervous by what’s in my opinion the perfect East Coast town.

“Ok… we can meet somewhere else. Where would you like to meet?” I replied.

“There’s a diner in Plainfield that’s nice. We can get cake.” was his response.

Not exactly my idea of a hip and happening location for a first date, but the idea of cake seemed to put Dick at ease. I met him the following night for cake, coffee and a very interesting conversation.

To say Dick was timid would be an understatement. He was very soft spoken, almost borderline meek. It was difficult to get him talking. I got him talking about his dog, his house, and a little about his career. The conversation really got interesting was when I asked him if he likes sports, and if he follows college football.

“Oh no, I don’t like football. Too rough. I do play tennis. My Ex and I played tennis a lot.”

And so it starts… why do people talk about their Ex on a first date with someone new?

Dick continued, “My Ex is a really good player. He played in college and almost went pro.”

With that, my inner Hardy Boy took over and I started to connect the dots. “Your Ex is a tennis player that lives in Westfield?” I asked.

“Oh God, did you sleep with my Ex?”

“No, pretty sure I can say no to that. Is his name Dick too?’
“Oh God, you DID sleep with him!”

This brings us to the first Dick.

“No Dick, I didn’t sleep with Dick,” I said, which made me start to giggle. “I’m sorry, it’s just kind of funny to me that I went on a date with your Ex, who’s also a Dick.” It probably didn’t help matters that I was still giggling.

“Oh, he sure is a dick!” said Dick.

“I went on a date with him early in the summer. Totally not a love connection, but he seemed like a nice guy.” And then I had to ask the question that 99% of the time only affects gay couples. It’s the very reason why I don’t plan to ever get involved with a Craig.

“When you guys were together, how in the hell did you deal with being Dick and Dick?”

“He’s crazy!” said Dick. “It’s very hard for me to talk to him, which is why I didn’t want to meet in Westfield and risk seeing him. And this isn’t the first time this has happened- everyone has had a date with Dick.”

Of course, that comment made me laugh, and again, I was not helping matters. Even though I was giggling, I really thought that Dick was going to breakdown in tears over Dick. He was visibly upset, and it was obvious that he was nowhere close to being over his Ex.

“Why does the topic of the Ex always come up on a first date?” asked a rather shaken up Dick.

“It doesn’t, Dick,” I replied. “There are so many topics that are in bounds for a first date, but the history you shared with someone else shouldn’t be on the field.”

Dick continued to lament about his failed relationship with Dick, sharing more information than anyone needed to know. It was evident that there was one too many Dicks at this table. I finished the last few bites of my lemon cake (which was actually pretty good considering it came from a big rotating cake cooler; the ones that really should be the New Jersey state mascot) and waived at our very nice waitress to bring the check.

Needless to say, there will not be a second date with Dick… or with Dick.



The major lesson learned in this not-so-fine date is one that a lot of daters have not mastered. When you have someone new sharing time with you, they want to know about YOU. They want to see if there’s a connection; a commonality that could lead to something more. Daters are looking for attraction.

On a first date, what is more of connection buster and less attractive than a conversation about an Ex?

I believe the “Case of the Two Dicks” might just give the answer. When I went on the date with Dick #1, he never mentioned his past relationships. Not once. We talked about sports, shopping and the fashion and music of the 80’s. It was fun and easy, but in the end, I didn’t find him attractive and there was simply no spark. Obviously from knowledge gained from Dick #2, his Ex is an active dater. I can safely assume that Dick #1 has successfully moved past his last relationship and is ready to embark on the next.

As for Dick #2, he is nowhere near ready to board the USS Next Relationship. His refusal to meet for a drink in Westfield due to his fear of seeing his Ex was the first sign. Dick’s reaction when I mentioned someone that happened to be the Ex in question sealed the deal- Dick isn’t over his past relationship.

I’ve given a lot of thought to whether or not any of us are ever truly over someone from our pasts. I believe in many ways our Exs have left a mark on our hearts and our brains forever. There’s a very big difference between being aware of the influences past relationships have given us, and being held hostage by the ghost of a past spouse or partner. Those of us that trend toward the former have their past relationship in a perspective that allows them to move forward. Those of us that trend toward the latter are the ones that bring up an Ex on a first date. Those of us that trend toward the latter probably need to re-evaluate their entry into the dating scene. Perhaps what’s holding them back from 1FineD8 is going on a date too soon.

Bottom line- don’t discuss your Ex on a first date. If your date brings up the subject of past relationships, simply don’t take the bait. Change the subject, and if your date persists, tell them that Gangnam Style was so last year too, and you’re not discussing that either.

D8 with Dr. No

Meeting a first date at one of the Ninth Avenue bars in Manhattan’s Hell’s Kitchen is an acceptable venue for any gay New Yorker, and it was perfectly conducive for my first date with Frank. We decided to meet at Industry, which has a fun and happening Happy Hour. When I spotted him at the bar, I was pleasantly surprised that he looked even better in person. Sharp dresser, nice brief case, and a very welcoming smile, Frank was definitely a happening mid-fifties guy.

We grabbed a drink and went to the couches on the side of the bar, allowing us to have a semi-quiet conversation. And what a conversation it was- it was as if I had known Frank for years. From home décor and DYI projects to shopping a great Lord and Taylor sale, we had a lot in common. We shared a lot of laughs, and there was definitely a spark.

The next topic on deck was music. Frank wanted to know my favorite concert of all time.

“That’s easy- definitely Prince and Sheila E.! Three of my fraternity brothers and I drove to Indianapolis to see them, and it was amazing. Gee, that must have been ‘85… maybe ’86.” I responded, taking a sip of my Heineken Light.

And then, as if a pack of beavers built a dam on my 1FineD8 River, the flow of our conversation came to an abrupt halt.

“Wait- you were in college in ’85?” asked a surprised Frank. “How old are you?”

“I just turned 49 this past July,” I responded. “I thought we covered the age thing in our pre-date conversation.”

“Oh. Guess not. I just assumed you were in your early 40’s,” said Frank. “ You don’t look that old in person.”

That old? I was a little puzzled by the point this fifty-plus man was trying to make.

“Well… thanks… I’m flattered you thought I was younger, but 49 really isn’t that old, you know.”

Frank didn’t respond.

The conversation continued, but with a very different tone. Thanks to my coming out as a 49-year old man, the spark was out and cold to the touch. I forgot what led to Frank making the following comment, but it was like an announcement from the Emergency Broadcast System telling me to evacuate the date.

“Guys our age like to date younger.”

I didn’t even need a second to respond.

“Totally disagree, Frank. I want to be able to have a conversation with a date about 1985 and get a spark of recollection in return. I don’t want to be a history teacher, even to a cute 27-year old”.

With that, the date was over. I went my way, and I assume Frank went off in his “One Direction”.



Sean Connery is so timeless that his portrayal of James Bond started in 1962 with Dr. No, and ended in 1983 with Never Say Never Again. He was 53 when he last played James Bond. He was almost 60 when he was named People Magazine’s Sexiest Man Alive. Sean Connery is living proof that sexy can be achieved at any age. I think Frank somehow missed this memo, and it seems likely he would have said “no” to James Bond.

I fully admit that I liked Frank. He was cute, smart and funny- and the right age for me. I would have easily asked for a second date based on how the first part of our first date went. The challenge was that I was the only ticket holder for the 2ndFineD8.

Sometimes, our date says “No”. They might not come right out and say the word, but they will drop the clue that a second date isn’t going to happen.

Guess what? That’s OK.

The sooner we accept that we are not going to be everyone’s flavor, the sooner we can brush off the defeat and move on to the next round. Some dates may not like your sense of style, and some may not like your profession. Some dates may not appreciate your sense of humor, your age, and may simply say that you’re not their “type”. Regardless of the reason, it’s not a fine date if the spark is one-sided. We all deserve a date, and eventually a relationship, where there are so many sparks from every angle that you both have no idea which one actually set the fire.

Again, it’s OK if you hear a “no”. Being on the receiving end of a no is never the way we want to end our evening, but once we come to terms that this might happen, the sooner we can bounce back and be on to the next dating adventure. Before you know it, you’ll be on that fine date where the only “no” you hear is “I want to get to “know” you better!”.

D8 with the Answerman

The text exchange I experienced with Glen was a lot of fun. He was a very witty and quick thinking high school teacher at a Manhattan private school. History was his subject, and as a favorite of mine, we had lots of potential topics to discuss. The texting was very easy with Glen, and I thought it would be fun to take it to the next level and meet for a coffee, in spite of one red flag.

The history teacher had no history.

At 53, Glen has never had a substantial relationship. No former partners and he never had a boyfriend for longer than, say, six months. He’s never lived with a partner, solved problems with a partner, nor has he gone on vacation with a partner. He’s never raised a pet, nor has he hosted a holiday party with a partner. Is this a deal breaker? I’m not sure. Perhaps he’s been inundated with working on a Masters and focusing on his career. There are lots of possibilities as to why he put his personal life on the backburner. Glen seemed to be very steady in his resolve to commit to a relationship and was excited about creating some history. On that, I decided that sharing a Venti Frappuccino couldn’t hurt.

I met Glen for a coffee in Midtown. The conversation at Starbuck’s was one of the most interesting I’ve ever had on a date, but not in a good way. I could share the entire conversation, however each question I was asked ended in the same fashion. Here’s an idea of what conversing with Glen was like…

“Craig, who’s your favorite college football team?”

“Oh…”, I responded, trying to say Ohio State when Glen’s hand went into the air motioning for me to be quiet.

“My favorite team is Penn State.”

From favorite TV shows to restaurant recommendations, his hand was in the air and my answers were “Frr..”, “Ahh..”, “Eee” and “Buh…”. I reached a point where I thought I was auditioning for a remake of the film Nell, and I was up for the Jodie Foster role.

At first I thought it was sort of funny, but then it became both annoying and illuminating. It explained to me why Glen has no history with men. Who is going to be able to take a steady diet of giving “Ack…” and “Chr….” responses and seeing Glen’s hand in the air all the time? I realized that if I were in a relationship with Glen, he would have the answers to everything from where we are spending the holidays, what we would name our dog, and where we were going on vacation. When it came to problem solving there would be no consensus because Glen is the Answerman.

My breaking point was when Glen asked me where I was from in Ohio. “You tell me, Glen. You tell me,” was the response I gave through a giggle as I finished my Frappuccino.

“What’s so funny?” asked Glen.

“Well, Glen, you haven’t let me answer one question. You shushed me so you could answer your own questions, again and again. Seriously, Glen, what have you learned about me in the last 20 minutes?”

Glen was rather flabbergasted, and perhaps a little embarrassed. He knew I was unfortunately correct in my assessment. I wished the Answerman all the best and was on my way.


My date with Glen took me back to freshman year of high school and my first communications class. I remember Ms. Ganz teaching us the importance of listening. “Listening allows you to learn and empowers you to respond intelligently”. Listening is even more important than speaking, and to that end, you have to allow your communication partner, be it a dating scenario or not, to actually speak.

The best way to discern if your date will lead to a 2ndFineD8 is to really listen to them, and that means allowing them to speak. Learning your date’s likes and dislikes is important, but gauging their sense of humor and intelligence is critical. Is there a sparkle in their eye when they speak? Do you hear a welcoming tone in their voice? Perhaps the combination of both with the words they say are telltale signs that they are flirting with you? You’ll never know the answers if you never allow them to respond.

When you’re on your date, ask your date questions about themselves. Hobbies, career, their Alma Mater, and pets are great places to start. You’ll be able to learn quite a bit, such as if they’re an overall positive person, their sense of humor and their excitement levels on each topic. Let the conversation flow, and enjoy the ride!

I’m not sure if being the Answerman is the real reason why this history teacher has no chapters of relationships past in his own private textbook. Not being able to get a word in edgewise kept me from asking. My hope is that if it plays a role in his lack of success in the dating world, he took my feedback and applied it to his next date.