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Following my Valentine’s Day dating epiphany, I decided a girls’ night out was necessary, so last Friday I called on Nigella, who is one of my partners in crime and headed out with only one mission to accomplish–have a fantastic time sans romantic expectations (the best-laid plans of women and their friends, often go awry). Nigella and I became friends during college and immediately discovered a common bond based on a love of Latin men and affinity for dark sarcasm.

I also invited Ruby, though she had dinner reservations with her new mystery man. They had met recently though she was already walking around with that dopey, new romance grin on her face and I wanted to meet the guy who was responsible for making her smile in that way; however, Ruby was being extremely secretive…perhaps she didn’t want to place a jinx on the relationship at this early stage.

Nigella and I began our evening at the W Hotel, located on Lexington in Midtown. Cosmopolitan in hand, Nigella professed, to me, her love for the bouncer and swore that she would one day marry him…well, at least hook up with, if not marry. He was tall, dark, handsome and well…as protector of the gate, which led to Happy Hour bliss, he was built like a crazy bull; Nigella thought this was incredibly attractive and continued to swoon. I found this entertaining as I sipped a gin and tonic while suggesting Caribbean sites for Nigella’s and ”Raging Bull’s” nuptials.

Suddenly, a young man appeared to my right and asked if he could buy me a drink and we began chatting. He seemed fairly intelligent and creative, as he told me about his career as a chef working in Murray Hill. My conversation with Terry was going well; we laughed, joked and consumed many drinks. And where did Nigella go? Oh, there she is–SCORE! She is flirting with the bouncer.

Terry was about to ask to be excused so he could bum a cigarette outside the bar, though didn’t leave before picking my brain regarding the topic of smoking.

He asked, “Do you smoke?”

“No”, I replied, “Though I did until quitting two years ago.”

He replied, “Oh, are you going to hate me if I leave you here for a moment to get a quick nicotine fix?”

I laughed and said,”No worries, I understand the temptation to smoke when drinking; I won’t castigate you.”

Terry looked at me, with a look of sudden disgust, horror and confusion, turned on his heel, left me sitting at the bar, and never returned. I didn’t understand; what was his problem?? Was it something I said…oh yes, it must have been. I suddenly realized he didn’t recognize the word castigate, as in to scold severely…he interpreted the comment as “No worries, I understand the temptation to smoke when drinking; I won’t CASTRATE you.”

Yes, intelligent indeed.–Frankie

Dating is hard;dating in NYC is harder

Dating is hard, and dating in New York City is harder. The reason: no one actually dates in NYC. It’s more like auditioning for a Broadway show or a television series.

I think of dating as kind of an innocent thing, where two people meet and they go out to dinner and decide if they like each other and try it again before something more blooms. That kind of dating, I only see in romantic comedies staring Tom Hanks, Meg Ryan, Renee Zellwiger or Colin Firth.

My fling with Elizabeth was no exception. It was fun and fast. We did things that I never thought about. It was surreal. She was very strong and very appealing. I couldn’t believe how much I liked being with this beautiful woman. She liked to push me up against walls and kiss me or we would make out in Victoria’s secret dressing rooms, while trying on underwear. But the romance was short lived. She wanted a serious relationship and there was no way I was going to make that sort of commitment with a woman I had just met. Plus, I felt kind of funny about being with a woman at all. I felt like I had a big old scarlet letter L on my forehead and any minute rocks may be thrown at me.

The way I felt wasn’t right, but it was just the way it was. I felt some sort of self hatred. I really loved being around Elizabeth the few days we were together, but at the same time I hated that we couldn’t walk down the street hand and hand without guys gawking at us and screaming, “You two are together!? Awesome. Can I watch? You want a threesome?”

It was humiliating and I felt weird telling Frankie that I was seeing a girl too. So when she asked about this mystery date for Valentine’s Day I used pronouns such as “they” and”we” in order to keep her from knowing too much. God, what would my family say if they knew?! I didn’t even want to go there.

Elizabeth and I went to Zen in Union Square. We had a great dinner, purely vegetarian. After a few drinks, we both decided that it would be best if we remained friends because she wanted a relationship with another lesbian and I didn’t know what I wanted. So like at the end of an Ally McBeal episode we parted amicably and I walked home underneath the street lights, in my own solace, happily single. -Ruby

Secret Agent Stoopid

A few years ago, I introduced my friends Sascha and Derek; now, Sascha feels a need to return the favor by setting me up with her colleague. Though I know I was successful in my matchmaking and she is happy with Derek, Sascha enjoys vicarious thrills courtesy of my experience on Manhattan’s dating scene. Dense Brosnan was a candidate for the C.I.A and though he would have made Jessica Simpson seem like a Rhodes Scholar, he did have 8-pack abs and a sweet new B.M.W. This man was not really someone who I would ever consider dating seriously, though what harm could there be in having dinner? Plus, I had to do it for my friend; she was curious to discover whether all that packaging could deliver or if it was just for show.

I agreed to let D.B. take me out one Thursday evening; correction, THE most romantic Thursday evening of 2008-Valentine’s Day. Thursday is a good first date night, as many people are out and about on payday and the possibilities are limitless. If the date is amazing you could stay out all night, go to work Friday, and then recover on Saturday. If you are hoping to hear someone yell, “FIRE!!”, from the kitchen by the time appetizers arrive, you may then just call it an early evening citing your need for at least eight full hours of sleep on school nights. We arrived at Josie’s, a cute place in Murray Hill, which caters to the healthy set. All this man-child cared to discuss was his favorite person…D.B. How he attended Rutgers, though didn’t fare well academically due to his dedication to extracurricular activities, i.e. supporting women’s rights (to move into his bedroom) and Chemistry Club (discovering which liquors mix best to produce the best shots). Don’t get me wrong, I have enjoyed many late night games of Asshole, though, I didn’t major in Strategies to Acquire the Golden Beerpong Ball and Plastic Cup Trophy either. Oh my, his shirt did complement his pecs so nicely. Yes, fine, his pecs…and biceps…and ass were all tight and healthy; though every time he opened his mouth I wanted to fill it with a steamed organic Belgian potato & broccoli dumpling! He must have thought I was entirely too generous with my appetizer, though truthfully, I couldn’t stand listening to his insipid tales of debauchery from college and wrestling pseudo-presidential-attackers to the ground from the academy.

After dinner, we made our way to Snafu, which is a bar I frequented with friends during college and though I no longer spend many evenings there, I still return occasionally for happy hour. Though I passed by the bouncer without a problem, D.B. was stopped and asked for identification. I noticed a New Jersey license sitting conveniently inside a photo pocket, though D.B, of course, HAD to fish for and then, after a good two minutes, produce his MIGHTY AGENT I.D. I believe it was Shania Twain who once said, “So you’re a C.I.A. probie…That don’t impress me much…”-Oh no, that was MY LINE! D.B. and I sat on a sofa in a dark corner upstairs overlooking the bar area. He began kissing my neck and nibbling on my ear, “Damn”, I thought, “that feels amazing”. Somewhere between Dirty Martini #2 and breathtaking kiss #3, I realized D.B. lacked in conversational skills what LimpDick lacked in sexual prowess. From what Ruby and I had discussed, LimpDick was her intellectual equal, though she could no longer be the sensual instructor to his dunce of seduction. I sat here with Secret Agent Dodo, enjoying an electrifying, passionate kiss and when we stopped I wondered if Ruby and I would have to choose between sexual and intellectual satisfaction?? Oh good grief, if that is the case, then I will never settle down…such a dilemma is one that I should not have to consider…I want it all damn it!!!!!!!! Furthermore, I DESERVE IT ALL!!!! I finished my drink, savored the olives soaked in Grey Goose and asked D.B. to drive me home…it was, after all, a school night.–Frankie

The Break up; the hook up

Yes, I dumped him. I’m evil. I know it. I did it by text message. He was trying to convince me to stay. He said that sex wasn’t that important. Not important! I was like a freakin’ virgin, and a stressed out crazed lunatic. Yes, I was.

Last Saturday night I went out with some of my friends. It was my friend Cindy’s birthday, who I have known since high school. Cindy happens to be a lesbian so logically we went to a to a lesbian bar called Henrietta Hudsons. Henrietta Hudsons or “Hens” is a rocker chick bar on Hudson, not too far from where Frankie and I live in Chelsea. On Saturday nights Hens can get pretty wild and packed.

I was buying my friend Cindy a dance from a go-go dancer (who was dancing on the bar) when out of nowhere this attractive girl with a blond boycut offered to buy me a beer.

“Thanks, but that I have a boyfriend,” I said.

“It’s ok. I’m not here with anyone, and you have a friendly face. Come on. Let me buy you one,”she said.

“All right, it’s up to you. What’s your name?” I asked.

“Elizabeth. Yours?”

“Ruby.”

Elizabeth is 29 and an investment banker. She had recently broken up with her girlfriend because her girlfriend was cheating on her. She was having a hard time meeting Ms. Right. I was having a hard time not finding her attractive and the fact that she looked very similar to a pretty boy did not help matters. I kept silently reminding myself that I had plans to meet Limp dick early on Sunday and was not into girls. Cindy knew better and pulled me over to the side.

“Hey,” said Cindy. “So you’re doing pretty well, Ms. Chatty. Do you miss it? She’s cute. “

“Cin. I haven’t been with a girl since you in high school. Seriously, I don’t know. She is cute though.”

“Ruby, you’re not that into Limp dick so why not? You want to end things anyway. Right?” Cindy asked.

“I guess. I don’t know.”

Well, as you’ve probably guessed I did wind up hooking up with Elizabeth. It was fantastic. The next morning I sent Limp dick a text message: It’s been fun, but I want more. Goodbye. -Ruby

Obviously For Some…Just Not Hard Enough

Two weeks before Valentine’s Day…though I am not really all too excited. I am viewing it as just another day. Well, I guess that’s because I am single. How cliche, you might think, but I swear I’ve got my reasons. Last year I had a boyfriend and was living in a foreign city.

I’m not having much luck in New York so I think that if dating in New York fails that perhaps next year I will try being single while living abroad. Eh, screw it, I have truly found that men are the same around the world; only the scenery changes. Bright sunshine, warm weather, and tan skin just seem to make a bad situation more bearable.

Last year, I had a bit of affection and not much sex…ok, I can’t lie…no sex. I could count on one hand how many times I was laid over a five month period. Strangely enough, this V-day, though I am not expecting flowers, dinner, or seeing a film…though I am looking forward to a crazy evening of lustful bliss. Say what you may, but fuck buddies are in.

I met Adam a few years ago and he was my first and only Internet dating experience. We went out for drinks one evening and decided there was definitely an attraction, though we were totally incompatible for anything other than a sexual relationship. Quite simply we had great sex and have kept it that way for the past few years and what a great way to see the city from so many different boardrooms, rooftops, boiler rooms…You get the picture?

Plus, if I continue calling on Adam when I am not involved exclusively with anyone, I don’t worry about sleeping around. My principles aren’t compromised and I am completely satisfied. What a wonderful world! When involved in a relationship, I am quite a loyal girlfriend. Though when single in this city, it can’t hurt to call in the reserves, when necessary.

I am still reflecting on Adam’s and my latest “date” when I walk into my apartment, which I share with Ruby, who is in the bathtub buried beneath a mountain of bubbles and on her way to the finish line at the bottom of yet another Ben and Jerry’s pint.

The poor girl is considering breaking up with a boy…er…man…whom I have blessed with the moniker–Limpdick. Poor Ruby…I would love to tell her about my latest “date” at The Lincoln Building…the beautiful view from his office on the 52nd floor is enough to get me hot and bothered…and…mmm…I must say…the man is talented …WAIT! FOCUS!

“Ruby”, I say, “ice cream and the hot bubble bath are great…though we both know his soft serve is not your flavor”, as I scoop another mouthful of Chunky Monkey from the pint, “no matter the topping, he will never satisfy you”.-Frankie

Dating is hard enough, but dating in NYC is harder

It is two weeks before Valentine’s Day, quite possibly the most miserable day of all. No, ironically enough I’m not single, but I’m considering being single.

It wasn’t that long ago that I was. Only six months, but I’m down to my last pint of Ben & Jerry’s Chunky Monkey, I swear ( I’ve eaten about 20 in the past month and a half). As I sit in a steamy hot bubble bath (the perfect place to eat ice cream during the winter), I’m wondering how this happened to me, why I always meet the wrong men, and if there is something wrong with me.

So this guy…what can I tell you? My roommate, Frankie and I call him limp dick, because its rather true.

Limp Dick and I met over drinks and appetizers at House during a work venue. I work in publishing where everything is quite incestuous, but I had never seen him before. Now we’ve been seriously dating for six months. Six months is kind of a deadline. It’s either stay or go. It’s either going to work out or it isn’t. And even though after six months, he has been the perfect gentleman and does everything right socially, I’m really considering dropping this relationship because sex is that bad.

Seriously, I don’t know what I’m doing wrong, but it’s definitely his issue. I’m not a nympho or anything, but come on! We are dating; I’ve got blood pumping! He was perfect, except for sex or the lack of thereof. Seriously, the other day I greeted him at the door of the apartment in black high heels and a black silk thong, and the man thought I just got out of the shower and told me he would come back in ten minutes. Really! So he’s 28 and impotent, super Catholic, or in the closet.

Limp dick was never really into sex. When we first started fooling around he wanted to “slow down”. We laughed, we talked, and we became great friends. The first time he froze up. He just hung there like meat in a freezer. I tried a few um things… the usual. Its never failed before, but he might as well have yawned. So I decided to spice it up. I bought porn, I bought sex toys (that I wound up using on myself), underwear. Nothing worked. He wouldn’t go down on me because he didn’t understand the workings of a woman’s “yoo-hoo”. So I got him a book. It was quite mechanical. In; out. In; out.

So I told my roommate, Frankie.

“Dump him,” she said. “Not worth the trouble. Damn, that was a waste of six months,” she added.

“You’re right,” I said. “I’ve had better sex with women. I don’t need this,” I added.

Well, that was two weeks ago and here I am in the bathtub with Chunky Monkey dripping down my chin and into my bubbly bath water.

“Damn, Ruby. It’s steamy in here. Oh, yeah, it’s decision time is it. Six months. So dump him babe,” Frankie said as she walked into the bathroom and sat down on the toilet.

“I know. But what if I never meet anyone,” I said.

We both laughed.

“Oh Chaquita banana, you know that ain’t happening,” Frankie said grabbing the spoon from my ice cream and shoving a spoonful into her mouth.–Ruby