Vinny 41, New York, Dating

I read Vinny's email in detail.

"Dear Jenny,

Thanks for writing back! I hope you having a great day. I read your stories and appreciate the thought and details you put into the dialect. I am a 41 year old fan of your material and want to share my appreciation for your efforts. If we were to have communications, I assure you that I would treat you with the upmost respect. You, like all women, deserve nothing but the best from a man. While I am not known as a wasteful man regarding my expenditures, I have a lot to offer a stunning female such as yourself. Below is my picture. I am a kind soul and hope to have the opportunity to prove that to you.

Sincerely,

Vinny Destario"

I have to be honest, I am really taken back by his looks. Despite his age of 41, Vinny looks like and older and chubbier version of George Castanza. Vinny has to be an easy 220 lbs, maybe 5'10" and has a huge balding spot in the center of his head. His flannel shirt and blue jeans look like they hopped out of 1965. Never in a million years would I normally give this guy the time of day. I'm not saying I'm a 10/10, but he's maybe a 2.5/10. If he didn't have nice teeth, and Italian name and a huge smile, I'd say 1/10. That said, I am ****. I begin to think; If I'm with a guy who is well below my league according to societal standards, maybe he'll be more helpful with my finances.

Despite my stale interest in him, I decide to do some research online. Vinny has worked at the same insurance company for 18 years. He lives in a 3 bedroom house in Long Island, New York. His town is about a 30 minute drive from me. He is currently the branch manager for the Soho, Manhattan region of a Fortune 500 insurance company. Vinny does not appear to have ever been married. His hobbies include Star Wars, Nirvana, Anime and Ice Cream.

I respond to Vinny,

"Dear Vinny,

So happy to hear from you! Thank you for getting right back to me. I can tell from your pic that you are a strong and happy man. You seem like the type of guy who can make a girl smile :). Your emphasis on respect makes me feel safe and secure, like tight hug during a scary thunderstorm. I'd love to learn more about you and see if we can be friends. Wanna meet at Midtown Comics at 5:00pm Saturday? We can walk to Central Park and talk. If all goes well, we can get some ice cream?

Love,

Jenny"

Vinny quickly replies,

“Hello Jenny,

Yes that works perfectly. I know the spot very well. If you get there early, tell Julio and Ahmed begins the counter that I say hi! See you Saturday at 5:00!”

Okay, I guess I’m going through with this. I have never dated a nerd before and have absolutely no idea what to expect, let along what to wear. I decide that since he is a flannel kinda guy, I might as well give my tiny jean shorts a twirl. I find a grey top, black heels, put my hair in a ponytail and head out.

When I arrive, he is waiting in front of the store, dressed in a blue button down dress shirt 3 sizes too small and an oversized pair of slacks. She smiles when I arrive and asks if I’d like to look around. Despite having no I interest at all, I nod my head yes. He tells me all about the comic book cartoon characters as he sorts through the bin of magazines. H after 10 minutes of boredom, I suggest we walk to Central Park. He says “okay” and we begin the 10 minute walk.

5 minutes in, Vinny can no longer hold in his exhaustion. Sweat is dripping down from his bald head, his shirt is damn around the collar and he is audibly huffing and puffing like a dog. I asked if he’d like a break and point towards a nearby bench. He replies, “if this place okay with you? It has fans” and points to a pub.

I normally wouldn’t be caught dead inside a dive bar at 5:00pm, but the break and A.C. Does sound nice. The darkly lit pub had a long wooden bar with a dozen stools. At the end of the pub is a pool table and a dart board. The three men at the bar are all sitting apart and look like miserable Ohio transplants from 1980. Vinny enters the pub with a smile and wave saying, “hello everyone!” All three guys mumbled “Hi Vinny” without looking up. I guess he’s a regular at this dump.

At this point I think there is no chance he can save my family. It doesn’t appear that he has a penny to his name and I am wasting my time. I will politely accept 1 drink, then say goodby forever.

We find side by side stools at the end of the bar and have a seat. The bartender looks at Vinny then looks at me with a confused look. He looks back at Vinny and says, “the usual house beer?”

Vinny replies, “Not today Chuck, a Long Island Ice Tea for the lady and myself please”.

The bartender rolls his eyes as walks down the bar, grabbing a bunch of bottles.

Did he just order me an ice tea at a bar? Just because I’m a tiny Asian girl doesn’t mean I can’t have a real drink! I take a deep breath, smile, and tell Vinny, “Thank you for the drink. I heard that you offered us ice teas from Long Island. I’m actually okay with an alcoholic beverage.”

He looks at me with a confused look for a second, then gives me a jolly smile alongside a Santa-like chuckle. He responds, “The Long Island ice tea has some liquor in it.”

While waiting for our cocktails, Vinny askes me "tell him something interesting about my life." I presume he is hoping for a funny story, personal information or a long ago event, but I use this as an opportunity to address my economic needs. I tell him about my parents accident and how out house will be foreclosed without immediate funds.

Vinny looks me in the eyes, places his huge, sweaty hands over my tiny, well manicured fingers and says, "I'm sorry, Jenny."

A moment later our drinks arrive. We cheers and take a drink. Vinny takes a huge first sip. I don’t want to look like a wimp, so I follow. I **** as a swallow, not expecting it to be so strong. Vinny laughs, wipes my chin with his napkin and tells me a joke tea. I chuckle and take another sip while he tells me another, even more humorous joke.

Vinny finishes his drink and orders another. I’m tipsy and only half way done with my drink, so I have no idea how he does it. Vinny’s jokes continue as does his drinking. I’m starting to enjoy my kind panda with the puffy red cheeks. He orders a third drink as I am almost done with my cocktail.

It took three strong drinks, but he is now clearly tipsy. He looks deep into my eyes and began opening up about everting. He told me he is a virgin, hasn’t had a second date in nearly 20 years and is lonely. This is not the confidence a women wants to hear from a man on a first date. I start looking for a way out of this conversation, and ultimately this bar, but can’t find one.

He continues talking about how he thinks he is fat and ugly and no one wants him. At this point I don’t know if I should comfort him, pity him or just run. He finishes his drink and orders yet another one. He starts telling me about how not having sex throughout his life made him unhappy and he tried everything to get it. He continues to tell me how he has an Asian fetish and I’m the hottest women he has ever seen. He proceeds to tell me he goes to Roosevelt Avenue in Elmhurst, Queens (a known red light district) and tries to get Asian prostitutes, but he’s always scared when they look or talk to him. He starts to stares at me with a lustful look and I quickly look away. My eyes are on my drink. I'm not looking at him, but I feel his eyes on my legs and breasts.

Disgusted beyond belief and believing this has been a waste of my time, I reach for my purse to leave. This might be the creepiest guy in NYC. As I’m about to get up from the bar stool, Vinny attempts to get up and starts a new topic of conversation, “I need to use the bathroom, but when I come back remind me to tell you about how I haven’t spent a penny since graduating college and I have over 700k in my bank account. See you in a moment hot stuff!"

Vinny shuffles his fat body off the stool, almost falling as he does. He stumbles to the back of the bar, swings open the bathroom stall door and enters.

What do you do?

1) Stay in the bar and continue the date in the bar.

2) Wait for him to return, then tell him you are going home.

3) Wait for him to return, then ask to continue the date elsewhere.

4) Run out while he is in the bathroom.

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