Single and Dating Life: Wink Not, Want Not

What do you do when you get set up with a “great catch”? Well, you feel like you’ve hit the jackpot!  Here is a great dating story from Darcy Dates about just that very thing … but as we all know, sometimes the shiniest bling blinds us from the true imperfections of the gem …

He was tall. It’s really all that mattered to me from the get go. He also had a cool interesting job that wasn’t the typical wall street, lawyer, executive job. It was cool. It’s something you wanted to tell people about. It was a blind a date.

We met at a cool restaurant in the Meat Packing District. I love the Meat Packing District just as much as any bridge and tunneler does. For one, it is not my neighborhood, so it seems like a vacation from the mundane. I remember years ago, when I was in high school, all that was there other than prostitutes and meat carcass’ hanging on steel hooks was my very first nightclub I had ever been to. Mars. But now the Meatpacking is a completely different place.

I met Craig for our date. He was as tall as he claimed to be and cute, if you looked past the hair gel. He was a little too “outfitted” for me, and spared no mention that his “outfit” was from JohnVarvatos. I didn’t want to know that much about what he was wearing, other than, I was hoping he would remove his jacket, which he didn’t, because apparently it was part of the “outfit”.

The moment we sat at our table, the DJ, yes, there was an actual DJ with turn tables in the restaurant, started to increase the volume of the music. Craig informed me that he wanted to “kick the guys ass” and “shove his headphones down his throat”. I was taken aback. Is Craig trying to be funny and falling flat? Or does Craig have an anger problem? Craig was very twitchy and I casually asked if he dabbled in any recreational drugs. He assured me he didn’t. “Good. Drugs are a deal breaker for me.” I said.

Craig was also divorced, but had no children. Craig and his wife lived apart for work reasons a year into their marriage and Craig’s wife picked up a new beau. Craig was still angry about this, even though he pretended not to be. Craig quickly bragged that he got to keep all his money and got the ring back. These were things that I felt he should keep to himself. It made me a bit uncomfortable.

Soon a large party was seated next to us. One of the guys at the table went to take off his coat and Craig got pissed that the guy took his coat off so close to our table.

“HE HAD TO TAKE HIS COAT OFF RIGHT NEXT TO OUR TABLE? WTF” Craig said in a huff. Ah, anger problem, not trying to be funny, I thought. My next thought was I wish Craig would take his jacket off too.

Craig then tells me we will be going to another hot spot in the Meat Packing District for dessert. Craig knows every word to every song the DJ is playing. He sings along to every song and break dances with his upper body. I find it very uncomfortable and wish he would stop. Not so much the singing along, because I myself like to sing along with every song, and I would say I am almost an idiot savant of song lyrics, but I could do without the re-enactment of Breakin‘ 2, The Electric Bugaloo the entire meal.

Then the winking starts. Just a PSA to any men (or women) who may be reading this: If you must, a strategically placed wink in a conversation is acceptable. Several winks during said conversation is awkward and borders on socially unacceptable. Craig tells me after our dessert and the next location, we will go dancing. I am trying to formulate excuses to extract myself from the situation.

We get to our next destination. A very hot spot right now where it is nearly impossible to get a table. Craig knows the “bouncer” or “host” or whatever they call the man in charge. Maitre’Dmaybe? Who he gives a big bear hug to. He quickly shows Craig our table. As he walks through the restaurant all of the staff, waiters, hostesses, and bus boys are slapping his hand. It is a scene from Goodfella’s, Craig’s hair gel included. Craig tells me he brings people there for work all the time. Craig works with celebrities. That explains it.

We sit and Craig orders us dessert. He continues to wink at me incessantly, it is not a tick, he just thinks he is being sexy, and I ask him to take off his coat. He tells me it is part of his outfit and again mentions John Varvatos, but this time mentions that he spent 4k there earlier that day. I cringe.

The funny thing is, anger problem, hair gel and winking aside, Craig is a nice guy. Certainly a good-looking one. I felt like i was being hard on Craig. Craig tells me he has a confession to make. At this point nothing can shock me. He tells me he has a roommate. I am too tired to find it off-putting. He explains that when he moved back to the city post divorce he had his best friend live with him, “But I have the Master Bedroom, and Master Bathroom.” Of course, I think to myself, wondering why he would ever think that made a difference. Craig was a few years younger than me. Maybe this is what young single people do these days, I thought. I begin to yawn and tell Craig I should start heading home. Craig tells me he would never want me to take a cab this late at night and insists on driving me home. I think that is sweet and certainly makes him a gentleman. His apartment is literally on the corner and we can go pick up his car after dessert.

Craig asks me if I want to see his apartment which he is very proud of (obviously forgetting he is a grown man with a roommate). Out of morbid curiosity I oblige, “Only for a second” I say.

When we walked in, it was exactly how I expected it to look. It looked as though Huffman Koo’s threw up in his living room. Black leather couches, faux modern art in shades of brown and taupe, also probably bought at Huffman Koo’s or won on The Price is Right. “Very Nice”, I said through my teeth, “We should leave before the roommate returns.”

Craig drove me home, lip syncing and break dancing the whole way home. Craig keeps trying to book another date. I have yet to accept.

So is winking a sign that a guy likes you?  I just keep picturing the old “finger point and wink” … it’s all cheese baby!  He obviously thought himself a great catch, he was quite high on himself … in his eyes he was so cool.  Who cares what type of clothes you wear and where you live, don’t get me wrong, it’s all nice, but I’m of the opinion that people should just notice, you shouldn’t have to point it out.  But you know what, I think he was totally taken with our friend Darcy and was trying to impress her the only way he knew how … so should she give him another chance?  I would say yes, just to see what the second date was like … and the winking? Well, ask him if there’s something in his eye …

Make sure to check out for more great dating stories and follow her on Twitter! @jenakingsley

Your Sister in Dating Bliss,

Single Dating Diva

Copyright Single Dating Diva


  1. Miss Diva, thank you for sharing this experience. It was quite entertaining to read. All of what you described above made me think of my-man Denzel in American Gangster, “The loudest one in the room is the weakest one.” Craig is “too loud” and seeks attention and constant praise. I think you should go on date #2 anyway and then post your experiences again for us to read.


    • Thank you! I am so glad you enjoyed it! It’s sadly all true. I didn’t go on another date, but I have been on tons of bad ones that will keep you entertained! I like that quote from American Gangster! So true. I am going to have to remember that one!


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