Tag Archives: First Date Advice

D8 with the Man without a Face

Photos play an integral part in online dating success, and the photo of “Ed” left a lot to be desired. I could see a camel, a lot of sand and a little spot of a man riding the camel. It was the only picture “Ed” posted in his very well written profile. Because of his ability with words, I decided I would respond to his email.

“Ed” was a good conversationalist in the online chat, however he seemed to be very guarded and rather nervous. My experience told me that when a man exhibits extreme cautious communication, he’s most likely in a relationship and looking for some side action. “Ed” swore he was single; his challenge is that he is deeply closeted. His guard was up stronger than the Royal Guard on point at Buckingham Palace. In spite of holding his cards closely, I learned that we did have some things in common and he was within the age range of my dating pool.

Is the fact that “Ed” was so deeply in the closet a reason not to go on a date with him?

I agreed to meet him for a drink at the rooftop at the Peninsula, one of my favorite hotel bars in Manhattan. The spot of a man riding a camel turned out to be quite dashing, complete with a winning, welcoming smile. The conversation with “Ed” was very pedestrian- travel, food, and Manhattan neighborhoods. Nothing too deep, until I decided to grab my trusty shovel.

“So “Ed”, you seem to be rather guarded. Witness protection, huh?”

“Oh no… I’m just not out. Nobody knows I’m gay,” he responded with a nervous chuckle.

“You might be surprised. Good looking single man in his 50s can set off the “bet he’s gay” alarm”, I responded. “Besides, it really doesn’t matter because you’re on a gay dating site and it’s 2016 so there’s really no reason to be fearful.”

“I disagree. People think I’m straight, and I like that.”

“I see. And you like that. Is your name really “Ed”?”

He didn’t answer, which I believe was an answer. “Ed” didn’t budge in his resolve; he set up residency in his closet and he wasn’t coming out for me or for anyone.

an illustration of a faceless man in a business suit
Putting your best face forward on a date means allowing your date to see you both inside and out.

I FineLesson

As we wrap up Pride Month, it makes me sad that there are some gay people out there that still can’t publicly own the fact that they’re gay. It makes me sad to acknowledge that there are some people- regardless of sexual orientation- that aren’t fully embracing the magic that is them. It just makes me sad that people don’t embrace their own personal truth, whatever that truth may be.

If we can’t love ourselves, how can we fully expect to find someone to love us?

I know I’m sounding a little like RuPaul, but it’s a message that needs constant repeating. When beginning your journey in the dating scene, you need to do so with a full arsenal. By that, daters need to enter the arena knowing with certainty that they’re already in love with themselves. Daters need to embrace every facet of themselves, from their looks to their career. Self-love leads to confidence, and confidence is key.

Dating is really no different than selling. You’ve got to believe in the product that is you, or you’re going to remain on the shelf.

“Ed” obviously doesn’t fully believe in his product. He doesn’t accept himself on a basic level, and with that he will likely remain alone on the long term. Unless he finds someone identical in mindset, I believe he will likely remain single.

My hope is that all daters believe in the product that is them. Believe it so much that you deeply want to shout it from a rooftop. Trust me, it may take some time, but the perfect customer will hear.

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D8 with Mona Lisa Vito’s Brother

Tick… Tick… Tick…

We all have a friend that’s dying to have a baby. Some of those friends are in their mid-30s, and they feel the pressure of time on their shoulders as well as their unoccupied uterus. Married, single, in a committed relationship… it really doesn’t matter these days. What matters is that there’s no baby where a baby should be. This was never expressed so perfectly than by Marisa Tomei playing the role of Mona Lisa Vito in My Cousin Vinny. If you close your eyes you can still see the image of her violently tapping her foot violently while saying, “My biological clock is TICKING LIKE THIS!”

Here’s a news flash for Mona Lisa Vito… it’s just not women with a ticking biological clock. It happens to men too.

I’ve always had a soft spot for tall, blond and beefy, and Troy answered that description to a tee. We met online, and our fantastic banter led to a lunch date. He was also 50, and like me enjoys daily gym visits and has aged quite well. It was no surprise that we’d choose grabbing a salad at Chopt for our date.

The conversation was a lot of fun. His family, my family; his career, my career; his friends, my friends… it was a seamless exchange and quite fun until… he revealed himself as Mr. Vito, Mona Lisa’s brother…

“I really want children. Soon.”

“Ok,” I said. “Adopting an older child?”

“No, biological. One of mine and one of my husband’s… at least two.”

This was not the time to take a bite of the Chopt pita bread with a swipe of Tex-Mex Ranch Dressing. I almost choked.

“I see. And you want to do this… soon?”

“Absolutely- we’re not getting any younger!”

I quickly changed the subject. It’s not that I don’t like children- I really do. My parental friends know their kids love spending time with me. That enjoyment is quite reciprocal. I know I would have made a kick-ass Pop. I would have excelled in fatherhood, however I never wanted to do it alone. Looking at my past relationships I would have never entertained bringing a kid into the mix. Neither of my Exs were not interested in having a family outside of the two of us, or they would have been absentee on every level to the point that I would be parenting alone.

But in this case with Troy, it wasn’t having a family that made me change the subject. It was the idea of having a date, a boyfriend, a fiancée, a marriage and a baby in the time it takes to prepare a package of Stove Stop Stuffing.

We said our goodbyes, and I never saw Troy again. We texted a couple times, but scheduling a second date just didn’t happen. Who knows… perhaps one day I’ll see him and his gorgeous husband pushing a pram. I just hope they’re happy.

Roll 2
Before you buy the T-shirt, better make sure it’s a perfect fit.

 

I FineLesson

Since I was a kid, I’ve been a major fan of chocolate pudding. My dear friend Alice turned me on to Kozy Shack (it’s pretty darned tasty), and before that I was a big supporter of Jello Instant. It wasn’t until I had chocolate pudding made from scratch that I was rather blown away by the richness and flavor.

If it takes time and stirring to make a perfect pudding, why would you take shortcuts on something as important as your relationship?

Regardless of the motivator, having an instant relationship isn’t a smart move if you want that relationship to have staying power. Building blocks and foundations aren’t created overnight, nor are they created in two weeks or a month. Relationships with the flavor of a homemade chocolate pudding require time and stirring.

There’s no reason to settle for a relationship with a good flavor when you have the tool of time on your side to make that flavor great.

This especially holds true if you’re planning to make pudding for four or more. If not for yourself and your partner, at least consider those building blocks for your future family. Nothing requires deep and sturdy roots more than a family tree- plant that tree and enjoy every moment watching it grow.

D8 with Mikey, not Mike

There should be a warning label on email because opening email can be hazardous to your mental health. This was proven when I opened a missive sent by Mike.

Hey Craig- It’s Mike from Match.com. We spoke back in March, and we never had a date.                                 I’d like to fix that if you’re still on the market. Hope you are!

My gut reaction was that if a guy remembered me from eight months ago from an online dating profile I discontinued, I should give him a shot. After all, I did share my email address with him so I must have been somewhat interested.

So I gave him a shot.

Hi Mike- yes, I’m single and sure, I’d be happy to meet you for a drink!

I met Mike for a drink. He was a good-looking New Yorker with an interesting career and exceptionally well traveled. Like me, Mike was out of a long term relationship for a couple years and was open to pursuing a new commitment. He liked shopping at Lord and Taylor, uses his gym membership, and wouldn’t say no to a well-prepared burger.

And that’s where the similarities came to a screeching halt.

I was very happy to be on a date with someone that was not afraid of talking, but some of the things he was saying left me more frightened than visiting a haunted house filled with hungry zombies, a couple past dates and several Presidential candidates. Here’s a small sample of my fright night conversation.,,

I don’t date minorities- not a fan of their culture.

 I had this horrible date last week… an Israeli. I had no idea he was Jewish or I would have never gone on the date. Don’t date the Jews.

 I’m not a supporter of gay marriage- it’s not G-d’s will.

With each word spoken, Mike morphed into Mikey, the kid who hates everything.

As I continued to listen to his list of things he didn’t like, I couldn’t help but wonder how much fun he’d have celebrating Hanukkah with my friends and family, which include people with varied skin tones, accents and beliefs. I also wondered if he ever enjoyed Cuban food, sang along to a Four Tops song or thought about the federal and state taxation breaks that are extended to married couples. I had no choice but to respond, and did so in the kindest and most respectful way possible…

Well, Mike, I really don’t believe we have a lot in common. Marriage is my end game, I couldn’t imagine how boring my life would be without multicultural friends and exposure to their experiences, and like Bette Midler said in the movie “Stepford Wives”, I can spell “Big Jew” on my front lawn with pinecones.

Mikey’s date-ending response was short and sweet, delivered after taking a swig of his Bud Light.

 “It seems we’re on the same bridge, but in two separate cars going in opposite directions.”

I’m pretty sure it wasn’t the first time he said those words, and I highly doubt it will be the last.

You have to try a lot of cereal before you can find the right flavor and texture that will make your mornings perfect.
You have to try a lot of cereal before you can find the right flavor and texture that will make your mornings come to Life.

1Gr8Lesson

One aspect of dating that is not fun is the disappointment of a first date that doesn’t lead to a second. The disappointment that comes with not making a connection can cut you like a switchblade.

Disappointment, unfortunately, comes with the turf.

The reality of being on the dating scene is that you have to be ready to accept disappointment. You have to feel it and move on to the next opportunity. Just because you experienced a near miss frog kiss doesn’t mean that your mission to find the one is derailed by one lousy date. I’m sure Mikey from cereal commercials of yore had to endure several bowls of cereal before he found the one that gave Life.

When you’re on the dating scene, you’ve got to remember it’s a numbers game- the more you date, the chances increase that you’ll meet the one sooner than later. You can’t allow a series of bad dates discourage you because you really have no control over what your date is bringing to the table. What you can control is how you respond to the disappointment- don’t allow it to take hold of you and plan another date. Who knows… your next one might just be two scoops of greatness.

D8 with the Snazzy Sweater

At the beginning of Summer, I made the decision and the suggestion to consider taking a break from online dating and try to meet people in “real life, in-person situations”. Summer has turned to Autumn and as I slowly trade my shorts for my sweaters, I’m continuing the offline mission.

A recent Friday night of mine was booked with Jackson. I met this man at Gym Bar, a Manhattan hangout complete with a pool table, televisions set to sports channels and men in outfits ranging from suits to workout attire. When it comes to meeting a diverse group of men, a gay sports bar is a sure ticket that will hopefully lead to Dateville.

Jackson definitely stood out in a crowd. With a full beard and standing at 6’5”, Jackson was an eye catcher, and a poster child for lumberjack hotness. We had a nice conversation- definitely not the flirtiest or the funniest- but it was nice conversation. Maybe it was the sparkle in his eye or maybe the hint of a Southern accent, but there was something definitely interesting about him. He asked me to dinner, and of course my answer was yes.

As I was walking on that crisp Friday night to the restaurant to meet him, I thought about our past conversation. I could remember very little…. was this a bad sign?

Jackson was every bit as handsome as I remembered. And tall… very, very tall. We sat down, ordered our meal, and the waiter walking away was our cue to begin an exciting and stimulating conversation. Within two minutes I was bored.

I made several attempts to get the conversation going. “Tell me about your job”… “What are your favorite things to do in Manhattan?”… “Any fun summer vacations?”… His answers to all were rather dull, lacking enthusiasm and personality.

It wasn’t until I asked “How long have you lived in New York?” that things got somewhat interesting. Jackson arrived in the 90’s too, and this took our conversation to Manhattan of the 90’s, which is always interesting to me. We talked about restaurants like Universal Bar and Grill and bars like Splash and Private Eyes. When I mentioned Club USA, he smiled and said that he was a bouncer there.

Figures he was a bouncer- tall, good-looking and a man of very few words.

When the waiter asked if we wanted to try one of their pumpkin spice desserts, I said no and asked for the check. We paid and left. Jackson gave me hug and headed East and I made my way Uptown. It wasn’t said, but like the cool breeze that was bringing Fall to Manhattan, it was obvious that this was in no way a love connection.

Lots of sweaters from which to choose... sometimes you have to try on several before finding the perfect fit.
Lots of sweaters from which to choose… Sometimes you have to try on several before finding the perfect fit.

1Gr8Lesson

Dating is a lot like shopping for sweaters. Sometimes we see a wool sweater with a fantastically attractive design. It beckons us to try it on, and when we do we discover the sweater fits a little on the baggy side. Then we spot a nice blue V-neck, a total classic yet simple staple that never goes out of style.

Do we walk by the V-neck or do we give it a chance?

I wanted a date with Jackson just because he was great looking. I was guilty of trying on the amazing sweater, and at the time I made no apologies for it. I still make no apologies, even though my choice in sweater made me itch from boredom. By choosing the great looking Jackson, it made me wonder if I overlooked a sweater that might not have been as snazzy but may have been more my style.

It’s easy to get caught up in the exterior appearance of a potential date. Who wouldn’t want to walk into a party with a model or an athlete? The challenge is finding that person with the external looks that jazz us, but also with the smarts and the heart that keeps us interested.

The next time you’re “date shopping”- be it online or out in the field, keep in mind the whole package of a potential date. Maybe your future date is the snazzy sweater, or perhaps if you keep looking through the displays you’ll find that classic V-neck that’s just the right fit.