Category Archives: #datingadvice

Ten Ways to HoliDate!

Being single in a Winter Wonderland can be an interesting experience for us in the dating scene. With the hustle of the holiday season, most of us get caught up with attending and preparing holiday dinners, parties and other outings with friends and family. As a Dater, it’s easy to neglect our dating opportunities with “December Distractions”.

As Daters, we can’t afford to miss an opportunity for what could be an amazing HoliDate!

Turning that Winter Wonderland to a Wonderful HoliDate is actually a very simple thing to accomplish, and the week between Christmas and New Year’s is the perfect time to get into the HoliDating scene. Take my city, for example. There are so many things to do in New York, and with the backdrop of holiday decorations and excitement, the spirit of the season will provide a backdrop to 1FineD8.

Here’s a look at my top ten HoliDate ideas:

Turn up the heat with some hot chocolate in a romantic setting. Enjoying a hot chocolate or a coffee drink makes for a warm and tasty first date! One of my faves is Knave at Le Parker Meridien Hotel. You’re the boss when it comes to the milk to chocolate ratio, making your hot chocolate a one-of-a-kind specialized creation. For more information visit http://www.parkermeridien.com/eat/knave/

Knave provides the perfect backdrop for 1FineHotChocolate!
Knave provides the perfect backdrop for 1FineHotChocolate!

Be on the top of the world with the City at your feet! Nothing beats a rooftop bar, especially when it’s heated! Check out the specialty drinks and the view from the rooftop of the Peninsula Hotel. Great cocktails, and a view of the Fifth Avenue Snowflake that is unparalleled! For more information visit http://newyork.peninsula.com/en/fine-dining/salon-de-ning-rooftop-bar

Birds eye view of the Unicef Snowflake, thanks to the Peninsula!
Birds eye view of the Unicef Snowflake, thanks to the Peninsula!

Shopping and Skating and Snacks…. Oh My! Put the “S” in spectacular when you have a HoliDate at the Bryant Park Bank of America Winter Village. You and your date can do some fun shopping (stores close 4 January- hurry!) and take a whirl on the skating rink. Grabbing a snack at Celsius is the cherry on the sundae of this 1FineD8! For more information visit http://www.bryantpark.org/things-to-do/wintervillage.html

Fashion Week or not, nothing is more stylish than Bryant Park.
Fashion Week or not, nothing is more stylish than Bryant Park.

Taking in the holiday themed department store windows is picture perfect! Nothing says holiday like seeing the windows of New York department stores. I suggest meeting your date at Macy’s Broadway entrance, and from there head to Lord and Taylor. Walk uptown on Fifth Avenue, taking in all the store windows, and make a right after visiting Bergdorf Goodman. Head East, starting with Barney’s and ending with Bloomingdales. It’s great cardio, and the walk will give you plenty of time for conversation!

Take in the excitement of the holiday exterior of Saks Fifth Avenue.
Take in the excitement of the holiday exterior of Saks Fifth Avenue.

Keep warm with something… chilly. You’re already on the East Side from your Window Walk, so why not enjoy a famous Frozen Hot Chocolate at Serendipity! Of course, it’s romantic to share, but I always want my date to know the real me…. which is why ordering two is mandatory! For more information visit http://www.serendipity3.com/

A Frozen Hot Chocolate can be shared, but why when you can order two!
A Frozen Hot Chocolate can be shared, but why when you can order two!

Welcome aboard the Love Boat, 2.0. A cruise around Manhattan with that special someone can be a fantastic experience. From dinner cruises to rides with Carolers, there are many options, including New Year’s Eve! Check out the website below for the perfect sailing! For more information visit http://www.sail-nyc.com/NYC-Holiday-Cruise

Views of Manhattan are amazing from the Hudson River!
Views of Manhattan are amazing from the Hudson River!

Sometimes you just need a fireside hamburger! When I first moved to New York, one of my first dates as a new New Yorker was at Molly’s. This Third Avenue mainstay makes one of the best burgers in Manhattan, and the fireplace is romantic as all get-out! For more information visit http://www.mollysshebeen.com/

Mollys-pub

All you need is Love, Actually. There are lots of holiday movies from which to choose, but nothing really hits the heartstrings like Love, Actually. Enjoying this flick with your special someone before or after Christmas can make for one romantic date, especially if you include a little couch cuddling! When cuddling, all the cool kids are going undercover with Berkshire Blankets. Give one a try! For more information visit http://www.berkshireblanket.com

Keep your date under wraps with a warm and cozy blanket!
Keep your date under wraps with a warm and cozy blanket!

A little game playing can be a good thing. If you and your date are college football fans, you know that the fun begins on New Year’s Day. Need to find the perfect place to watch the Sugar Bowl? Try the SportChaser.com app! This new app will tell you the options available for watching your favorite games, be it college football in January or baseball in April. For more information visit http://www.sportchaser.com

Plan a date that will leave your date cheering!
Plan a date that will leave your date cheering!

Workout dates? No Sweat! Start those New Year’s fitness resolutions with a partner in crime! 24 Hour Fitness makes getting a guest pass super easy with just one visit to their website. You can do your own thing, or take a Group Fitness class together. With three locations in Manhattan from which to choose, you can pick the perfect place for a hot date without bother. For more information visit http://24hourfitness.com

24 Hour Fitness in Soho
24 Hour Fitness in Soho

Regardless of your home base, you can easily take inspiration from these ideas and apply them to your location. Every city has hot chocolate, all towns have cool burger joints, and ice-skating is pretty universal. One thing’s for sure… if you take advantage of the fun vibe and the excitement in the air, you’re one step closer to ending 2014 with a bang-up date!

D8 with Goofy, Charming, Aladdin and Doc

It’s a world of laughter and a world of tears,
It’s a world of hopes, and a world of fears…

Let’s focus on the fear for a moment.

I recently had a date with a gentleman named Bart. He was a musician in his early fifties, well known in his industry and had a large circle of friends and collogues. While enjoying a cocktail at Ritz Bar and Lounge, a fantastic Midtown venue, the conversation flowed like a well-written song. We reached the topic of vacation destinations. Bart lit up like the Enchanted Castle at night as he told me of his one and only option.

“I only vacation at Disneyworld!” exclaimed Bart, as happy as one of the Dwarves when Snow White rings the dinner bell. “I’ve gone every year since I was 19!”

I did the math. At 53, Bart has been to Disneyworld 34 times.

Bart is one of the handfuls of men I have met lately that are obsessed with all things Disney. By obsessed, I mean these are men that can sing every lyric to every Disney song. Men who not just know the plot line of every Disney story, but also can tell you the scenery, costuming and year it was released on DVD. These are men that are the first to pre-order the DVD of Frozen and the last to leave the theatre when they see Aladdin… for the fourth time. And when it comes to vacation, you can bet Cinderella’s pumpkin coach that they’re on a flight to Orlando dreaming of their check-in at the Grand Floridian because last time they stayed at the Yacht Club.

From my past experience with DisneyHolics, I knew that I had to be exceptionally careful in my approach.

“It’s the only place you go to on vacation?” I asked.

“Absolutely! Why go anywhere else?” replied Bart. “The resorts have everything you could want. When were you there last?”

This is when I remembered… the Disney obsessed believe everyone has taken a hit of Tinker Bell’s Magic Fairy Dust and feels the exact same way about the Magic Kingdom.

“I’ve never been,” I said with a smile. I might as well have told Bart that I singlehandedly drowned a litter of kittens.

“That’s just stupid- how can you miss out on this? It’s magical!” he said with undying enthusiasm combined with just a shred of judgmental disgust. “Where do you like to vacation?”

“I love the beach. When I think Florida, I think Lauderdale,” was my honest answer.

“Eww. Don’t like the beach. It’s hot and dirty,” responded Bart. “If things work out with us, I’m taking you to Disneyworld.”

That was probably the scariest thing a date has ever suggested, and I’ve heard a lot of suggestions. Disney is just not my thing. It’s a fantastic necessity if you have children. Not being a parent, a Disney vacation has never been on my radar. And he was very quick to nix the idea of the beach and the idea of relaxing seaside or poolside working on a tan and enjoying that Golden Sun.

There is just one moon
and one golden sun.
And a smile means friendship to everyone…

Let’s focus on that friendship smile for the moment as I plan my date-exit strategy.

It turns out planning my exit strategy wasn’t necessary- all it took was my answer to the following question… “Have you seen Frozen?”

“No, I missed that one,” I replied.

There was almost no need for a verbal response from Bart. His reaction of shock, combined with disbelief and horror could only be paralleled to finding out that I made a coat from the kittens I killed earlier and wore it out barhopping with Lindsey Lohan.

“I really don’t think we have much in common, Craig,” replied Bart.

At last- Bart said something that I could get on board with 100%.

“I think you’re right, and that’s totally OK,” I said sporting that friendship smile.

And with that, the date was over. I decided to take advantage of the warm, fall evening and walk for a few blocks. I wasn’t the only one taking in the beauty of Manhattan on this warm fall night- many were hitting the streets just like me. Smiles and skyline everywhere I looked. I realized that I was already in my own Magic Kingdom and somewhere in this enchanted land my own beach loving, HGTV watching and bourbon drinking Prince Charming is waiting for me.

MM

1Gr8Lesson

Being different is one of great things that make humans human. Different looks, different likes and different opinions can really lead to not just a fine date, but also a spectacular relationship. There’s nothing more fun than sharing points of view, and sometimes your own point of view may change based on the insight that others provide. Sometimes, differences are learning opportunities, whereas sometimes the differences are obstacles.

Sometimes there’s just one difference too many.

A love for Disney- even one that borderlines obsession- is not the strongest example of a deal-breaker difference but was one for me nevertheless. In my case, I know I could never be the partner Bart needs because there’s no way I’m spending valuable vacation time in a Disney park on a yearly basis. There’s also no way I’m curling up on the couch with him on a snowy Saturday watching The Little Mermaid for the 18th time. And I’m sure he would be just as enthusiastic at the prospect of a beach week in Waikiki or a marathon of America’s Next Top Model or Pawn Stars.

Some differences are much more serious, involving religion, politics, and whether or not a marriage is in the cards. As a responsible dater with our eyes on the prize of a lasting relationship, we need to keep our eyes open to the differences that could be deal breakers.

When a difference becomes a roadblock, it’s best to take a detour and get a new map.

Think about the difference in question and ask yourself, “Is this something I can live with… every day.” If the answer is yes, then chances are it’s not the biggest difference after all.

If the answer is no, then ask yourself if the entire “body of work” this person brings to the table makes the difference something you can live with every day. If the answer is still no, then it’s time to move on.

We know the road to “Happily Ever After” isn’t going to be easy, but discovering major differences in the beginning and making decisions based on them early on is much easier than suffering the ramifications of eating a poisoned apple.

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.

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1Gr8Lesson

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”.

martini-glass-clipart-5

1Gr8Lesson

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!”.