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D8 with The Man Who Cried Uncle

There’s nothing better than a fix-up date. It’s like going to a potluck dinner in Ohio… you have no idea what you’re going to get but chances are the recipes include bacon and cheddar so it can’t be all that bad. When my friend Tammy introduced me to Thierry, I was intrigued by the accent for sure. His look wasn’t one that I really find attractive (you know… that gaunt “I just escaped a foreign prison” look), but he had a nice smile and was friendly. It did, however, take him a moment to put down his wine glass to shake my hand.

We met at a dinner my friend was hosting, so it was a scenario of “Craig meet Thierry, Thierry meet Craig… and here’s a glass of red and the appetizers are right here.”

Whether I liked it or not, I was going to be spending the next few hours with Thierry.

Appetizers preceded a very tasty soup, which led to an amazingly prepared dinner. I had no idea exactly how much wine Thierry had to drink prior to being presented with a meal that rivaled anything on the cover of Food and Wine. What was noticeable was that he was quite smashed. Of course, what does a smashed guy do? Keep drinking. He was more interested in drinking than contributing to the conversation, which ran the gamut from Manhattan real estate to yea or nay on Manolos for a first interview to the versatility of fruit. I learned that fruit was more versatile than I ever imagined. Thierry had no comments on any of these topics, not even on the fruit.

The dinner conversation was a lot of fun, partly because of the other guests and partly because I purposely didn’t sit next to the red wine infused fix-up. Overall, Thierry was a pleasant enough of a guy. Again, he didn’t contribute much to the conversation, but that all changed when the topic turned to relationships. That’s when Thierry decided to let loose.

“None of you have relationships. You just fuck around. You’re fooling yourselves. I’m done looking for love. DONE!” said Thierry as he poured more red in his glass. “Everybody is fake. Nobody is real. Tell me something… when was the last time one of the men you fuck actually did something romantic for you? Tell me!”

It was one of those moments you wished you were back at a potluck in Ohio, where nobody’s overtly drunk and the most awkward question is “Did you vote for Kasich?”.

At this point, it seemed to be an unspoken consensus between the rest of the table that ignoring Thierry was the new bill of fare. Nobody answered his question. I felt bad for our host and the other guests because this drunken giver-upper on love basically called us all sluts with no substance. I really wanted to ask him when the last time was that he did something romantic for someone else, but we all know that rational communication is impossible for drunks. And I’m willing to bet that in relationships, the only thing Thierry would give his partner was a bottle opener if the partner was lacking.

For the remainder of the night, Thierry kept quiet as he continued to drink. Once in a while he would utter something, but it was impossible to understand. Sloppy, unattractive and a really bad guest were just a few descriptors that came to mind as I watched him sit there on the verge of a full fledged pass-out.

When the evening came to an end, I did my best Edward R. Murrow and said, “Good night… and good luck.” as I walked behind Thierry.

He didn’t respond- he just took another sip of wine.

Don’t be so quick to cry Uncle… tomorrow is another day, and another date!


A reminder of the importance of a two drink maximum while on a date was never better illustrated. Granted, this wasn’t a “date”, but similar rules of decorum apply when in the home of a friend. I have no reason to believe that Thierry and a bottle behave no differently in any social situation.

The real lesson was found in looking straight into the eyes of the agony of defeat. Seeing that look of utter sadness; the expression of being beaten down by the lack of finding love. It was actually quite sad.

Life is all about choice. Even in the worst of situations, a positive person will realize that it’s only for now and will keep walking- if not running- to the light at the end of the tunnel. It’s what strong people do. Choosing to make lemonade when given a bushel of lemons takes work and grit, as opposed to the easier option of staring down the bushel in anger and despair as the lemons rot. Thierry chose the latter- he cried uncle and gave up.

Turning a negative into a positive takes determination. Are you up for the task?

We all have bad dates, good dates that never call for seconds, and other dating disappointments along the road. What we do with them and how we process the experience says volumes about us. If you stay the race and keep your eye on the prize, you’re sure to win.

There will be days you’ll want to throw in the towel and give up. Don’t do it.

Our friends at NASA said it best… failure is not an option. Five simple words to live by in all facets of life, especially while on your quest for 1FineD8.

1FineVideo- When to Introduce Your Date to Your Friends

To introduce or not to introduce… that is the question! Thinking about introducing your 1FineD8 to your friends? You need to watch this video! Dateologist Tracey Steinberg and I tackle this question on this installment of Ready… Set… DATE!

Have you found yourself in this situation? Let us know and please share your experience!

For more information on Dateologist Tracey Steinberg, please visit!

Be sure to follow me on Twitter! @CraigRogersNYC

D8 with the Cool Cat in the Cradle

1985 was a fantastic year. I was a sophomore TV Communications Major at Capital University, and was already the Executive Producer of a popular weekly cable show. I was on Executive Board of my fraternity, and between being sorority sweetheart for the Deltas and my groovy Zeta pals, I never lacked for a “date” to a fraternity party (and yes, we’d go dancing at the Garage, a popular Columbus gay bar, afterwards). 1985 didn’t bring me a real boyfriend, but it did provide me with the perfect American college experience, complete with friendships I’m blessed to enjoy to this day.

1985 was a big year for Mr. and Mrs. Smith, too. They had a boy! I wonder if it ever crossed their minds while changing his diapers that there was a 20-year-old college boy out there that their baby would one day ask out on a date.

I’ve mentioned before that I have very little interest in dating men that are younger, and by younger I mean 40 and below. I’ve spoken to some friends- gay and straight- about the fact that even though my online dating profiles clearly state that I’m interested in men between 45 and death, the random twenty-somethings will still approach me. My friends’ reactions are very similar…“Do it!” “That’s hot!” and “Score!” are the top three responses. But my favorite, which came from a middle aged straight guy…“Is he a flight attendant or a nurse?”

There seems to be a consensus that dating (and I use that term very loosely) a twenty-something is something, if given an opportunity, is one not to be missed by any forty-something. Maybe it’s all about exposure to the boundless energy that comes with youth? Maybe, like my friend Coco Brown said, it’s because they don’t come with the baggage of lifetime disappointments in the love department. Or maybe it’s just an ego thing, delivering some sort of validation that a twenty-something is attracted to you.

I decided that perhaps it was time I found out. Justin was an accomplished 29 year old that I met at G, a Chelsea mainstay. He was very aggressive in wanting a date, and had a rebuttal for every excuse I gave. He was as persuasive as he was charming. It turns out that Justin is a member of a gym in Manhattan where I teach spin (Justin admitted to checking me out at the gym, which kind of scared me because I always look my personal worst in any fitness situation). I relented, and suggested that he take one of my classes and we could grab coffee afterwards. He loved the idea, and that was the plan for two days later.

The funniest thing happened during my “spin date” with Justin. As I was teaching a killer class, I looked at Justin, who incidentally knew every word to Katy Perry’s Roar and was fearless in singing along as he effortlessly rode. But the real action was in the row behind Justin, where a man in his mid-fifties was working as hard as he could, sweating to keep up with determination to do so. He was adorable. Two men before me- one was the athletic Justin, who sailed through class, and the other guy with the silver flex in his hair that was working it. I thought to myself, who’s more attractive… to me? The answer was simple, because at the end of the day nobody is going to know my favorite flavor better than me.

After class, I thanked Justin for coming, and told him that I hoped he continued to come to class. As for coffee, I politely declined, but was sure he would have absolutely no problem in finding a date. Like most twenty-somethings, Justin was beyond resilient and totally understood. He was fine with being friends.

A week later I had a conversation with the determined fifty-something man with the silver flexed hair. We’re having coffee next week.

cool cat


I’ve given a lot of thought as to why men my age sometimes are in dating relationships with twenty-somethings. I mentioned earlier that maybe it’s an ego thing, or a control thing or perhaps as a last ditch effort of reclaiming youth.

Maybe I was wrong.

Sure, those scenarios may be the case for some May/December romances, but meeting Justin and spending some time with him made me realize that I wasn’t totally correct with my summation of reasons. Justin has a lot of great qualities, and I realize that to judge him solely on his age is doing him a disservice. He will make someone a fantastic boyfriend. The reason he won’t make a great boyfriend for me is because I didn’t feel the attraction or connection I typically feel with men my age.

For me, and maybe for you as well, it’s really as simple as ordering from a menu at Peter Luger. If your palate is asking for aged prime rib, then why order the veal?

Spending some time with my new friend Justin reminded this old dog of a not so new trick- don’t be so judgmental of those with dating tastes that differ from mine. Not all May/December couples are built on a foundation that is sketchy. Couples are built on several types of foundations, and my hope is that each includes attraction, respect and love.

Those are three necessary relationship building blocks that are required at any age.

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.

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 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.