untitledAfter my disappointing cruise and failure to meet any normal guys online, I decided to take a break from dating. I deactivated all 3 of my online dating accounts and welcomed back a simpler time when checking my email was about receiving coupons and sale notices from my favorite department stores. I would stop holding my breath waiting for a notification that I had received a wink, a flirt, an email or an instant message.

So I stopped.

And I felt great! My confidence was coming back. I was spending time with my girlfriends on the weekends. I was shopping like a maniac decorating my newly purchased home. I was reading again. I was back to doing the things that made me happy. And it was working.   I was happy.

And then one day I received a friend request from a guy from my past who I had reservations about for a plethora of reasons but who convinced me to go out on a date with him after two weeks of texting and getting to know each other.

So over sushi and sake one Friday night we had our first date. We had our first kiss. And instead of heading our separate ways at midnight, he decided to join me on a weekend get-away I had previously planned with my family.

He met my family. We held hands. We snuggled in bed with no expectations. He showered me with compliments. We had an amazing time together.

But driving home I knew I was in trouble. Our amazing first date had lasted 36 hours and a few minutes after dropping him off….

I missed him.



A year ago, my psychic told me that the man I would spend my life would be the type of guy who my family and friends would judge and it would be my job to show them all why he is the love of my life.

So when I received an email on Match from an overweight Harley riding tattooed fisherman from Suffolk, I replied, considering that the people in my life would surely judge this guy!

My psychic also pulled a tarot card during my reading that had two wings on it and he interpreted the card to mean that together we would be two wings and together we would fly.

So when Justin told me that he flew planes I started browsing wedding magazines and picking out baby names.

We were definitely different….that was for sure! But through his emails and then texts, I really started to like him. He was an absolute sweetheart.

After a 2.5 hour phone conversation we decided to meet for coffee.   I prayed I would be attracted to him….

Justin was big. Justin was a very big boy. He was 6’0 tall and probably weighed close to 300lbs.

I’ve never dated a guy with a few extra pounds on him and Justin had a bit more than a few extra pounds but he really was such a sweet guy…..

Assuming he would be able to fuck me I figured I’d be able to get over the weight issue.

Plus, as we headed into Dunkin Donuts I felt like a size 2!

I loved talking to Justin for those 2 hours. He was so cute and interesting. He thought I was a hoot and told me that I was even more beautiful in person. We talked about riding his Harley together and told me where I could buy riding boots. He offered to take me out on his friends boat so that we could go fishing. I told him that I’d never been out to wine country and he told me that there is no better way to experience wine country than on a bike in the summer and that he’d love to take me out there.

Before leaving Dunkin, Justin asked me what my plans were for the coming weekend. He asked to take me to an early dinner Sunday night and I told him that I’d love to.

It doesn’t happen often that I’m asked out on a 2nd date before the 1st date ends so I was beaming from ear to ear as we headed out.

He walked me to my car. We stood in the parking lot for anther few minutes chatting.   I was patiently waiting for a goodnight kiss, which never came, instead we hugged.

We would kiss…when the time was right.


Justin: Heyyyy I had a great time tonight. I just got home.
WinterInNYC: Wow that was fast! I had a great time too – thank you again for the coffee 🙂 I know u sacrificed for me and didn’t get ur Starbucks
Justin: Anytime! I had a great time as well. It’s ok about the Starbucks. I was in good company so I was happy 🙂
WinterInNYC: 🙂



WinterInNYC: What’s up?
Justin: In bed LOL dog was sick all night and kept me up
WinterInNYC: Ugh
Justin: He’s really not doing well. I’m gunna take him to the vet now. Something is wrong.
WinterInNYC: Poor thing 😦 keep me posted
Justin: Starting to worry me
WinterInNYC: He may just have a bug. See what the vet says. Try not to worry.
WinterInNYC: Everything ok?
Justin: They r doing tests….
WinterInNYC: u ok?



WinterInNYC: Justin?
Justin: Hey. Sorry I didn’t get back to u last night. Came home after the vet and passed out. They kept him at the vet for observation.
WinterInNYC: How’s he doing?
Justin: He was really crappy last night when I left him. Gunna head there in a bit.
WinterInNYC: What r ur plans for today?



WinterInNYC: I’m so confused

Not hearing back from Justin was so surprising and incredibly unexpected that I started to think that something had happened to him.

I thought his dog died. I thought his father died. I thought his plane crashed. I thought he got into a motorcycle accident and was in the hospital.

There was no way after the date we had, the fact that he asked me out for a 2nd date and called and texted the previous two weeks as often as he did that he was blowing me off.

He was dead. I convinced myself.

But then one quick call to his office Monday morning confirmed that Justin was alive and well.

Nothing had happened to him.

I just went out on a date with a dick.

If you can explain to me what happened, I’ll either blow you, or blow your husband/boyfriend for you so you don’t have to!


It started with a wink. Continued with a bunch of great emails. Followed by flirty texts. He was interesting and he was interested in me. His emails and texts were filled with questions, important questions about what I was looking for in a relationship and was I close with my family?…not what kind of underwear did I wear?

On a random Wednesday, about two weeks after the wink, Sal asked me to grab a drink.

We met at a very nice Italian restaurant in my town and for 2 hours we talked and laughed and flirted.

He was 31, Italian, lived only two towns away from me, had his own apartment, a nice car and a great job. And he was hot!

We shared a romantic kiss outside of the restaurant that first date and when I texted him that I had gotten home safely, he texted back that he had a great time, couldn’t wait to see me again and liked my soft kisses.

The next day he texted early to see how my day was going. He asked when he could see me again?

That night I had an engagement but we texted throughout the night. When his friends stopped by and I offered to let him go he texted, “Why? You’re not bothering me.”

It was a pleasant change from my ex who basically forbade me from texting him when he was out and when I did he would just ignore me for hours on end.

Friday he texted me that he had plans with a buddy but that their outing should end on the early side, would I like to meet up with him after?

Of course!

At 9pm Sal texted me that he was home. He wasn’t up for going out but he invited me over. While I tried to figure out if I should go to his apartment for a 2nd date, Sal apologized for putting me in that position. He didn’t want to give me the wrong idea about him and understood that I probably wouldn’t want to go to his place so soon.

I mulled it over for a few minutes and finally decided that I felt comfortable seeing him at his apartment and watching a movie.

I walked into his bachelor pad and he gave me the grand tour.

In his foyer area he had all of his military awards and pictures hanging on the walls….and then I saw it…a signed picture of George and Laura Bush.

My gut reaction was a quick chuckle followed by an “Oy” followed by an eye roll and then I ended with a “I can’t believe you have Bush on your wall!”

Although I considered that night to be a super romantic 2nd date watching a comedy, holding hands and smooching, I later found out that Sal was trying to deal with the fact that I made an impolite comment about a President he liked, who he felt took great care of him and all members of the military while in office.

Our budding relationship was lost from the moment I uttered “Oy”.

The next 2 weeks his interest in me waned. He stopped asking me about anything of importance. Although I saw him two more times after our 2nd date, both times happened because I initiated the get-togethers. And, although we had fun (at least I thought so) when we saw each other, there was no push to move the relationship forward.

I randomly ran into Sal on Easter Sunday at a gas station. He came over to my car and we chatted for a bit.

Later in the day I texted him:

WinterInNYC: Seeing you today was a tease!
Sal: Why?
Winter InNYC: Because I like seeing you and 5 min at the pump isn’t enough!
WinterInNYC: Guess I shouldn’t have said anything.
Sal: Look, I really like hanging out with you but I don’t see this going anywhere.
WinterInNYC: Of course this isn’t going anywhere! We barely talk and you have kept me at arms length for the past month.
Sal: That wasn’t my intention. I’m just being honest.
WinterInNYC: Thanks for letting me know.
Sal: Sorry :-\

I was crushed.

I’ve lost guys before.
I’ve lost guys before for not being pretty enough, skinny enough or smart enough.
I’ve lost guys before for being too clingy.
I’ve lost guys before for being Jewish.
I’ve lost guys before for not being dirty enough or for being too dirty.

But in all of my 33 (almost 34) years on this earth, I have never lost a guy because of my political beliefs.

It ended with a bush, George Bush.

I can’t catch a break. Apparently there is no middle ground for me in the online dating world. I either meet a guy that won’t text me back for days or I meet a guy that when he doesn’t hear back from me within….8 minutes….turns into a needy little bitch.

Which brings me to Tony, a 36-year-old decent looking guy with a good IT job and his own house (in the same town as me) who would flip out if I didn’t respond to his texts RIGHT AWAY….

5:58pm – Tony: Can I call u when off train
6:01pm – Tony: ??
6:06pm – Tony: Guess not
6:09pm – WinterInNYC: I put my phone down!

The funniest part about this is that I’m a super fast responder to texts. Most of my friends know that if I don’t text back right away it means I’m having sex, taking a shower, driving or pissed at them. So for someone to freak out on me for not responding quickly enough only showed me that this guy was fucking suffocating.

At 9pm Tony called me and we had a great conversation. We talked for over an hour and when I hung up with him I was optimistic that I had just met a really nice guy. I’d just ignore his earlier texts…I’m sure that’s not his norm!

I was getting ready to throw on some porn and get into bed with my vibrator when I got a text…

Tony: Sweet dreams
WinterInNYC: 🙂 u too
Tony: u are adorable
WinterInNYC: 🙂
Tony: I was really sad to hang up you are really easy to talk to
WinterInNYC: Thanks – there will be more to come
Tony: What type phone u got?
WinterInNYC: Iphone
Tony: Facetime for a min with me
WinterInNYC: No
Tony: Why
WinterInNYC: Bc I’m tired and not wearing makeup and ready for bed
Tony: Stop I don’t care
WinterInNYC: But I do – please….
Tony: Not nice at all
WinterInNYC: I am nice – Gnite Tony
Tony: Wow
WinterInNYC : I’m tired
Tony: Whatever that is mean
WinterInNYC: No its not!
Tony: It is. I leave you alone sorry

But the mother-fucker DIDN’T leave me alone…for the next 30 minutes I had to explain to him why I didn’t want to Facetime and why he should be more understanding.

He just wouldn’t take no for an answer! The memory of our first great phone conversation quickly vanished and was replaced by this ridiculously horrible nonsense child-like texting. He was exhausting and this was the first day we started talking….

I finally turned off my phone realizing he had drained all of my energy. Bad night all around! Not only was I too tired to play with my vagina but I was pretty confident that Tony had one too.

We were off to a great start!


I’m fishing. I’ve been fishing. I’ve been fishing my entire life. I’m sitting in the same fancy boat with my bedazzled rod and my yummy bait and I’m waiting…for years I’ve been waiting. I’m pretending that fishing is fun. I won’t admit that I’m losing hope. I won’t admit that my patience is wearing thin. I’m still waiting for a healthy delicious attractive fish to come along and get hooked but instead I wind up (sea)sick and (sun)burned with smelly fingers and I’m alone because I had to throw back the crap fish I did catch that werent fit for human consumption.

My last two rejects catches….

Name: Steve
Location: Queens
Age: 34
Employment: Insurance Adjuster

Steve: What do you do?
WinterInNYC: I’m a __________ __________ in the city.
Steve: Ouch
WinterInNYC: Yeah
Steve: Long commute 😦
WinterInNYC: Its ok. 45 min on the train.
Steve: That’s not that awful, you must get a bunch of reading done
WinterInNYC: I do! Do you read books?
Steve: Mostly magazines. U? 50 shades? Lol
WinterInNYC: I read a lot – and yes I’ve read 50 but it’s not my normal type of read
Steve: Uh huh sure lol
WinterInNYC: 😛
Steve: Bad girl! I like it
WinterInNYC: Why does that make me bad?
Steve: I hear its naughty
WinterInNYC: Read it and find out.
Steve: That book may be a little much for my virgin eyes and ears

I didn’t feel the need to find out if Steve really was a virgin. But I knew that if my reading of 50 Shades of Grey made me a “bad girl” in Steve’s eyes then one perusal of the contents of my night table would result in Steve cumming in his panties or crapping them (maybe both…at the same time).


Name: Frank
Location: Long Beach
Age: 37
Employment: Electrician

Frank: Can I ask you a personal question?
WinterInNYC: Ok
Frank: I better not u might get mad 😦
WinterInNYC: Might as well ask now that you brought it up!
Frank: Do u wear thongs or g-strings?
WinterInNYC: Strippers wear g-strings – is that what ur looking for?
Frank: Not only strippers wear g-strings silly guess u wear grandma undies lol
Frank: I guess u aren’t interested I will delete your number

This time…I have no words.


Vince (cute 31yo from Match): I think you’re really hot, You want to have some fun in my bedroom?

Me: Uh….Thanks! Sorry, but I’m not that kind of girl. I’m looking for a relationship.

Vince: It was worth a shot!

A few days later…

Vince: Hey beautiful! How are ya? I would really like to take you out.

Me: I’m not looking for just sex! I’m looking for a relationship. Are you up for that?

Vince: Sure. I think you’re really hot, lets go out sometime.

Me: Ok…

Vince called me on Thanksgiving and we had a good conversation for over an hour. He apologized for his 1st email and told me that he really wasn’t that kind of guy.

We ended the phone call with him telling me to text him tomorrow.

Me: Hey! How’s your day going?

2 hours later….

Me: What? Change your mind?

Vince: Yeah, sorry.

Me: Can I ask why? Thought we had a good chat.

Vince: We did. I’m sorry. I’m just not ready for a relationship.

Me: I don’t have “marry me” written on my forehead!

Vince: Yeah I know. But I have commitment issues and you seem like a nice girl. I don’t want to hurt you.

Me: Ok. Thanks for the heads up. Good luck.

Fast-forward 1 week….I got on the train headed for work and just as I sat down I received a text.

Vince: Did you just get on the train?

Me: Yeah!?!?!?!?!

Vince: I’m on the same train as you. I’m sitting a few rows back.

Me: That’s nuts. I can’t believe you recognized me.

Vince: Yeah, you look like your pictures. I saw you yesterday too but I didn’t think you’d want to hear from me.

Vince and I continued to text the entire train ride into the city. As the train pulled into the station, I was finally able to turn around and get a glimpse of my non-committal train stalker….Wow, he’s kinda hot!

Vince and I texted throughout the day and once again he asked me out. I was weary, considering he told me that he had commitment issues but randomly seeing each other on the train changed my mind….it was meant to be!

Friday night rolled around and Vince told me that he wasn’t feeling well. It was pretty obvious that he didn’t want to talk or see me.

Saturday afternoon I texted him to see how he was feeling and he didn’t respond.

Annoyed, that Vince was blowing me off, again, I signed back on to Match and gave my # to a guy named Joe that I had been emailing with for about a week. Six hours later Joe and I made plans to meet at a bar.

Huge mistake. HUGE! My hastiness resulted in not talking on the phone with Joe before meeting him. I didn’t screen properly and I was forced to have a drink with a very very very nice guy who, how can I say this nicely, who was a few cards short of a full deck.

On my drive home from my very sad date with Joe, I texted Vince.

Me: Because of you I just went on a horrible date.

Vince: Ha Ha! How so?

Me: You didn’t text me back today so I wound up going on a date and it was terrible!

Vince: You need to screen better!

Me: Yeah, no shit!

I was all dressed up with no where to go so when Vince said that he wanted to see me….I invited him over.

Vince and I talked for a while. Then we started making out. Which really wasn’t fun or exciting. His skin was waxy and cold, his lips didn’t move. I was kissing a dead fish. I felt nothing down there….Zip! Zero! Nothing!

To top off the night, when I attempted to find out what Vince was packing he stopped me within seconds telling me he was going to cum. Huh?

Yes ladies and gentlemen…I found another premature ejaculating fella. Must be the new fad. Everyone seems to have it lately! Two in one month! Yippeeeeee!

When he asked for a blowjob I refused.

Sorry dude but a 10 second bj really isn’t worth the effort. It takes me longer to put my hair up in a ponytail.

Vince was right…I do need to start screening better!

I recently decided to try something other than Jdate since I’m open to meeting someone who isn’t Jewish. Match was a total bust a few months ago so I signed up for Eharmony….AGAIN!

Eharmony’s process just sucks….and this go around has been just as annoying and unsatisfying as it was when I first tried it years ago.

The first decent guy to contact me was Russ. He wasn’t great looking and he wasn’t very tall and he dressed like a 60-year-old man in his pictures….but fuck my life I’m 33 already!!!

We made plans for drinks after work and we exchanged numbers to keep in touch.

I’m a total stalker so once I got his cell # I started my search on Google. Within minutes I realized that I had just made a date with a millionaire – Cha-Ching!!!!

He owned a hugely successful business AND a winery in Napa! His face was plastered all over the Internet, articles celebrating his success for such a young guy…there were even YouTube videos of him analyzing the industry he worked in.

Ugly or not I was going on this fucking date.

I arrived at the bar and realized that my millionaire date was the missing member of Alvin and the Chipmunks. He had this very round face with pudgy cheeks and these two white front teeth that seemed to show even when his mouth was closed.

Disappointed yes, but my internal mantra that night was, “Napa, Napa, Napa, Napa.”

Drinks went surprisingly well. We had a lot to talk about and he seemed genuinely interested in me. I even stopped noticing how closely he resembled a chipmunk at exactly the same moment he started explaining his process for making wine…

He walked me home like a gentleman and although it wasn’t particularly romantic he stopped me on the street and kissed me.

We made out some more in front of my building and agreed to see each other when we both got back from our vacations. He was leaving in a few days for a 2-week vacation and before he returned I was leaving for a week in Mexico.

That night he texted me to tell me how much fun he had on the date and how awesome it was to make out with me. I told him I had a great time too and was looking forward to seeing him again in 3 weeks.

The following night he texted me that he was in the neighborhood and wanted to give me a goodnight/goodbye kiss. I should have said no, considering I was already in bed naked half-asleep (it was 9pm), but after my missed opportunity with the Turk (which I plan to regret for the rest of my life), I ran around my apartment like a chicken without a head, cleaning my apartment, my body, getting dressed and putting make-up on.

9:20pm he was in my apartment.

9:21pm he was dry humping me.

We were both fully clothed and he was humping me and grinding on me so hard and fast that he was going to cum.

With every hump and bump and grind that I felt, I just kept reminding myself, “Napa, Napa, Napa, Napa!”

9:40pm I finally stopped him mid hump, rubbed out the soreness in my thigh, told him I’d see him in 3 weeks and showed him the door.

10:26pm he texted me: “I’m lying in bed so horny right now thinking of you.”

10:27pm I texted back: “I’m trying to sleep, talk to you tomorrow.”

Believe it or not I never saw Russ again….he actually blew ME off!!!

I guess I wasn’t his Chipette after all!!!