Saturday, December 12, 2009


Train guy has turned out to be even more interesting and more confusing than I could've imagined. He texts me during the day, signs in to chat with me at night and despite all this modern technology, makes me feel special and keeps me laughing all the time. But the never calling on the phone thing is weird. When consulting a highly trained group of professionals about the situation (read: my friends) they convince me he is married with children. Or in the witness protection program. Or gay. "Think about it. He can't answer the phone EVER. Because his wife is in the next room. Or you'll hear his kids in the background. Or the secret servicemen worry that you'll track down his actual location. Or he's gay." 

Of course, I call him. And of course he doesn't pick up. But he does call back in 2 minutes. I know, shock of all shocks! The worst part is, he sounds FINE! Tells me he's not married, not gay, has no children and cannot disclose whether or not he may be enlisted in the witness protection program as "they might be listening." Again, I'm laughing at the silliness of the whole thing when he tells me he feels like he's "going to hurl" and has to hang up. Phones make him nervous enough to puke! 

So I ask you, would you, could you, date someone that you couldn't speak to on the phone? Or is this just the tip of the crazy iceberg?

Monday, December 7, 2009

The Unusually Large Head

He got on at Jamaica station on the way to Penn. Asked politely if he could sit next to me. I nodded "of course" and went back to my book. He parked his slightly overweight self into the seat (a 3 seater, thank goodness) and I barely took notice. This is New York. We're used to confined spaces with complete weirdos. You're lucky to be on anything but the drunk express on Saturday night. Just pray to find a spot anywhere but the bathroom car. Have something to hide behind so no one talks to you. A book, a phone call, the newspaper, a paper-bag covered can of beer and a forlorn look on your face. Something that says "don't talk to me". But talk he did... there was no escape. I was pinned to that window seat for 42 minutes... possibly the best 42 minutes of my week!!!

It started with innocent admissions one could only tell a complete stranger. How we got onto the topic of him having an unusually large sized head is a blur, but that's where the conversation went. His inability to find a hat that fit well, how it affected the sports teams he had to root for because their head gear didn't fit him, how he wanted to dress up as the Mad Hatter for Halloween but even that costume was too small... He told one embarrassing story about himself after another and I have to say, I was captivated. His bad luck rivals my own and that says A LOT. He had me laughing so hard that my stomach actually hurt. I was a little sad when our train pulled in, I didn't want the fun to end. So I did what any girl would do, I gave him my number. He said he'd call and we parted ways. 

I got an email from him the next day saying that he was sorry but he told me he'd call because he couldn't actually call me for a fear of using the phone. Yes, an actual phobia of talking on the phone. (It's called phonophobia, look it up ... I did!) He was happy to text / email / facebook me but he can't talk because (are you ready for this?) he's "painfully shy and stutters a lot". This guy was practically a perfectly posed stand-up comic from Queens to Manhattan but if I called him he'd literally be sick to his stomach?!?! So we're friends on Facebook now and I will not be putting my book down on the train again EVER.

Sunday, December 6, 2009

Cop Kisser

He's gorgeous. Creamy Irish skin, red Irish hair, intense blue Irish eyes ... and drunk as an Irish cop should be on a Saturday night. It's not exactly coffee, we're at the bar with a group of friends. Me, Cosmo's and him, Guinness (I know, big surprise!) He's flirty in a safe, sweet sort of way. After just getting out of a show, everyone is in a good mood and we make fleeting eye contact throughout the night. Never lingering too long. Not thinking anything of it. But as we stand to leave, I know he's thinking more and more about those looks. Those looks that said, I want to take you home with me tonight. 

Sadly, I am not that kind of girl. No matter how "bad ass" I try to be, I always fall back on my sweetly predictable good girl behavior. If he wants to see me, he can call me and set up a date on purpose. I am not denying major interest in this 6'1 (6'2???) police officer from the Bronx. He's funny and cute and in better shape than I will ever be. He walks me to Penn station and kisses me good night on every corner from 23rd street to 34th. I leave him my number and he calls it right away. Feeling ridiculously confident, I turn on my high-heeled shoe in the snow and saunter off to catch my train. It is only when I look at my phone that I realize his number came up "Private" and I have no way to call him back :-(

Maybe I should've just gone to the Bronx!!!

Thursday, December 3, 2009


Here's a winner for you...

An email exchange with "promising" cup delved into discussions about our mutual love of cooking and baking. We traded kitchen favorites. He asked what my secrets were to delicious cookies, brownies, etc. I said a little bit of vanilla and cinnamon (yes, even in chocolate chip cookies) really enhances the flavor. He then went off on a tyrade about how vanilla hasn't been a secret for centuries. "Even Republicans are using it now." I jokingly said that if Republicans were using it, I would stop immediately. He wrote back with the longest political rant I've ever seen including but not limited to: "People our age are all stupid when it comes to politics, nobody knows what's really going on." "You know your opinion doesn't matter, right?" "What is it with women and Obama?" 

Sadly, we will NOT be meeting for cookies and coffee in the near future. I intend in altering my recipes from now on... for both brownies and men.

Saturday, November 28, 2009

Rejection Letters

First Round of Rejection Letters:

Some of these have proven to be more interesting than guys who actually have a prayer!

Dear Cups of Coffee, I saw your post and I realize that you're asking for guys ages 26 - 36. That being said, I am 44. But a young 44 if you can believe it. Please let me know if you're interested. 

Dear 44, Thank you but no, I'm not. 

Dear Cups of Coffee, I may be an epoch or two older than you but in my mind, age equals experience. I'm 59 and would love to meet up with you. Hey, it's just coffee, right?

Dear 59, You're older than my dad. Dude, that's gross. 

Dear Cups of Coffee, I read the four requirements of your post. I know you said ages 26 - 36, preferably white, straight and single. I am 22, Hispanic, mostly straight and mostly single. Would you consider me anyway?

Dear guy who obviously can't read or follow directions, Not So Much. 

Dear Cups of Coffee, you mentioned in your ad that you are 5'8. I'm writing because I'm 5'5 and most girls have a problem with that. I don't want to presume that you're that kind of girl. You know, a girl who would judge a guy because of his height. If you don't care that I'm 5'5 then I think you're a really good person and I'd like to get to know you better. But if you are that kind of girl and you want a tall guy then good luck to you. You bitch. Ok, hope to talk to you soon...

Dear 5'5, good luck to you too. And might I suggest a pair of heels for your dating future?

Saturday, November 21, 2009

Cup # 1

He said he'd be here in 5 - 10 minutes so I excitedly purchase 1 peppermint hot chocolate for myself and 1 pumpkin spice latte for him. It's my first "official" coffee date and while I know I cannot afford double drinks every time, this occasion seems like a reason to celebrate so I splurge just a little. Not too much; got "tall" not "venti". Trying very hard not to project the future onto every man I go on a date with. Besides, this is just the beginning. I have 99 more cups to drink after this. Or do I??? Ok, must stop thinking this way *right now*. Although his mother is a wedding planner which would be awfully convenient...

Bad sign #1. He's a half hour late. Bad sign #2. I'm on the phone with my best friend and she asks what I think of him. I say he's really nice. She replies "that means you don't want to jump him." I come back with how sweet he is and generous and hard working and thoughtful. She says "you still don't want to jump him." I hate it when she's right. Still, I shall persevere.

He finally shows up, button down shirt, khaki pants, hair combed. He made an effort to be presentable, especially after I know he worked a 10 hour day doing landscaping and custodial work. He's gotta be 6'2 - 6'4 (I'm not great with the math) so he towers over me as we say hello. I adore tall men but he's got at least 100 pounds on me as well which makes him a walking refrigerator. I worry what I've gotten myself into already. 

And it's all down hill from there. Half of my drink had already been consumed in the wait time for him. He did not shut up for an entire hour. (I know, I'm surprised I lasted that long too.)

 And the topics of conversation included: 
A) how he never went to his prom because girls in his school were all skanky crack whores 
B) how I'm the only woman "with any class" who's ever taken him seriously / given him the time of day 
C) that even though he's hit his head lots of times and in fact has metal plates holding his skull together resulting in mild memory loss, he is not *actually* mentally retarded despite being labelled as "learning disabled" in school but it only affects reading which he's not so good at anyway
D) how he is currently in a bit of debt but don't worry, "the lawyers are almost paid off" 
E) that his DUI probation should end soon as he's been on good behavior but if I want to drink on a date "we can always go to another state, cause they don't check up on that" and finally
F) that's he's 26 and still waiting for the right woman to come along (and yes this means he is a virgin)...

Am I seriously supposed to survive 99 more of these nightmares???

Tuesday, November 17, 2009

My first entry

Welcome to my blog. In this space, I will recount the tales of a single girl's attempt at finding happiness through dating. Not just any dating. 100 cups of coffee with 100 different men. I have challenged myself to sort through a giant pile of NO's in the hopes of finding one really amazing YES! Wish me luck!!!