Dating, Dating Challenge, humor, NYC, Online Dating

I Hate You, But I Love You


“Doctor by day, sexy Jon Snow by night.”

That was the description that date #1 had on his Tinder profile.

Doctor? Cool, must be smart. Sexy Jon Snow? Even better! Who doesn’t love an illegitimate Stark?

I figured that because this was my first date of The Challenge, it would be a great idea to go out for drinks with a fellow GoT fan. I mean, even if we don’t hit it out of the park at least we’ll have lots to talk about, right?

The date started pleasantly enough. I arrived at small bar in Kips Bay promptly at 5pm. Before entering, I took a ceremonious deep breath and said to myself, “Let’s do this!” – then walked inside like the diva that I am.

Skipping forward a beat, Snow walked through the door several minutes later, but alas, it was not love at first sight. From the moment I saw him, I knew our relationship wouldn’t last longer than one date. But I had a few hours to kill before I met up with my Babeland girls, and he seemed nice enough. Boy,  did I call that wrong. He was not a nice guy. He was, what my mom would call – after one or two margaritas – “a little shit.”

After learning about his job (he’s a psychiatrist), his family and glossing over a bevy of other first-meet questions, the conversation began to dwindle. That’s when he asked me about my tattoos, piercings and my recently-placed birth control implant (I still had the bandage over my arm, and a nasty bruise to go with it).

Now, while I’m a big fan of birth control, it’s not really a topic that I like to bring up on first-dates – mainly because it preludes to sex and I’ve found that guys can be a bit presumptuous. I mean, why can’t a first date just be about getting to know each other?! That said, he was a doctor, so the topic should be pretty safe. And it was. At first.

After continued conversation, we hit another lull – and that’s when he asked The Question:

So, I see that you have lots of piercings and tattoos… so you’re not afraid of needles…?

Umm… yeah. Sure, needles are cool. I guess. [Insert questioning look from me, here.]

So you you have a high tolerance for pain?

Well, I mean, I don’t think I’d withstand torture very well, but shots and things like that don’t bother me. (I think it’s important to note here, that I have a few piercings, but nothing crazy or out there. Just a nose stud and some ear piercings, as well as a few discreet tattoos.)

So, like… Does your tolerance for pain extend into the bedroom?

Wait. WHAT???? Did he seriously ask me that?

After a long pause Snow spoke up.

I’m sorry, was that inappropriate?

Seriously? Was that a question? HELL YES!

Yes, that was forward. That was really forward… I mean, just so you know, that was a very inappropriate question. 

There. I said my peace. While I could have (and should have) bounced right then and there, I still had 2 hours until I met up with my fellow Babes. What’s a girl to do? So I order another, stronger, drink.

To make a long story short, the rest of the date was relatively boring. I learned that we were very different people and had very different opinions. In fact, at one point, I escaped to the bathroom to text the group about my fiasco of a date, to which they said “bail now and come over early.” So I did just that. But not before Snow made one more statement: I can’t tell if I hate you, or if I love you. 


So with that, I bid the guy farewell, told him I hope to never see him again, and walked out the door like the boss betch I am.

But honestly though, no wonder the dude’s still single!

Love you betches!
Bossy Babe




The Subway Ride


Date #2

Oh New York – you always have a way of navigating me right into unique situations. Let me elaborate. We matched about four months B.T.C. (before The Challenge), but never met live. To be frank, I had no motivation to set that date up. I’m a millennial I’m supposed to be lazy! When I re-met him on the subway (RIGHT after my first challenge date) I realized that the MTA was essentially gunning for me to win and I figured I’d have to listen to it. It does take me to work daily after all.

When we locked eyes on the train, we exchanged the double take and I was filled with dread to make small talk the rest of the train home. Ya’ll know what I’m talking about… After we giggled about finally meeting in-person we exchanged the digits. Subway guy was the right dose of happy and unique. A bit older than me which is always interesting. Why not!? He met the criteria to get my second point (see post #1) so the date was set – NY Transit Museum.

A week passed. Prior to the museum, we grabbed tea and I instantly knew that I wanted the rest of the date to stay friendly. Poor guy. He was sweet, but when it doesn’t click, it doesn’t click, ladies and gentlemen. Oh and I was extremely tired*. I’ve been wanting to check out this museum so at least we had that going for us. It was in an abandoned station complete with historic trains so the history nerd in my was ecstatic. The single girl in me was slowly losing it. We chatted about the usual topics and learned how the MTA got through the city-wide black out but this girl had a nap to take. This museum seemed to get bigger and bigger. Or was it just me? Finally, after we got to the last vintage turnstile, I was able to rush home. Of course, we took the train home.

I realized that I was probably tied for second place and as much as I should’ve kept swiping, this girl had a nap to take. Sweet dreams, lovers.


Tea Babe

Dating, Dating Challenge, humor, NYC, Online Dating, Uncategorized

A Walk In the Park


Date #3

Sunday morning. Skies are blue. Birds are chirping. It’s cold as shit. I’m not hungover. Sounds like the perfect day for a COFFEE DATE!!! Never been on one of these before, but how could it possibly be bad? One drink + sunshine = efficiency. I get my caffeine, vitamin D, and date all checked off at once. 

This guy was hot in his Bumble pics. He only had two- at the beach with his “sister” and playing tennis in an all white get-up (just to be clear, his clothes weren’t the hot part, his face was). He actually really looked like someone who lived in my college dorm that my roommate was madly in love with senior year but never actually pursued. Turns out, she’s part of this challenge, too. Suck it betch. But I digress…

I didn’t really know anything about this person other than that he lives 1.6 miles away from me and knows the difference between your and you’re. But I’m excited! The first date of The Challenge that isn’t approached with dread- THIS is what it’s all about.

We decided to meet at a coffee shop on the NW corner of Central Park at 1:00. I get there at 1:00 and sit in the February chill in my cute-but-cold coat because all the inconsiderate Columbia students are taking up the entire cafe. Oh, you have a thesis to write?? I’m in a dating challenge, so my work here is obviously more important. Just kidding. I fully support higher education and all the work that entails. I am also well aware that finding a seat in a cafe within walking distance from a university on a Sunday is like seeing a unicorn barf cronuts onto the Loch Ness Monster. It doesn’t happen.

He walks over about 15 minutes later and hubba, hubba. I’m so into it. Yeah, he was late, but I liked him anyway. He had a great smile. I’ve never dated anyone who comes anywhere close to being as smiley as me and I was already looking forward to our next date. We ordered; he laughed when I took a Hydro Flask out of my purse to fill up with black coffee. And we decided to take a walk through the park.

The conversation was great. He asked a ton of questions about my job (teacher) and was genuinely eager to hear about my experiences with kids in the city. He’s getting his MBA from Columbia. He graduated from a school in Canada with an engineering degree but wants to take over his dad’s civil engineering company, so it was off to business school in the states for him. We walked around for about an hour before sitting on a bench in the sun, trying to thaw out.

Oh, I forgot to mention that I had a vampire facial the day before. Yeah, one of those facials Kim K did in that gif. The process is cool and it’s helping a lot with my acne scars BUT it makes your skin peel like a bitch for a couple days and you can’t put anything but hyaluronic acid on your skin. So I was wearing a baseball hat and big ass sunglasses the whole time and my cheeks were red and peel-y. I didn’t think about it the entire date until we sat down face to face. Oh, well. If the conversation’s still going strong, he obviously doesn’t care and neither should I, but I still brought it up before parting ways.

I’m wearing a hat because I had a scar removal procedure done yesterday. I’m not trying to be creepy and not let you see my face. 

What? Oh, hahah! I didn’t even notice!

I just don’t want to get sunburned and look even scarier for my students. 

You could never look scary. 

I could if someone threw acid on me.

Yeah….Well, I had a really nice time! Are you busy this week? I’d like to see you again. Maybe get some drinks with alcohol in them? hahah

Oh, you didn’t spike your coffee, too? ….(Moment of awkward silence) But yeah, definitely! I’d love to get drinks this week. Are you free on Tuesday?

Ahh. I have a dinner Tuesday, but it’s early. Maybe drinks after? I’ll let you know tomorrow.

Okay, perfect. See you soon!

And that was it. No kiss. No hug. Just a dorky grin that spread across my face as I walked back through the park blowing up the group chat.

Love always,

Art Babe



Dating, Dating Challenge, humor, NYC, Online Dating

Vanilla Ice


Date #2

If I wasn’t writing this I would have already forgotten about this dud. For the sake of The Challenge, I’ll dig into the depths of my memory and attempt to extract at least a few moments of this date to write about. If you’re in the mood for a juicy story, find another post. Nothing exciting here; just another example of the vanilla dates everyone finds herself on at some point.

The pre-date texting was decent- a bit of wit, responded in an acceptable amount of time. I wasn’t super impressed with his pictures. Come to think of it, I don’t remember a single one. Oops. Coming off the Boobtastic Brit, I was a little apprehensive about this challenge, BUT a girl’s gotta power through, right? Plus, I’m a Leo. I don’t turn down challenges.

Day-of texts

Vanilla: I know this great Pho place in Chinatown. Interested? Or we could just get drinks. 

*Babe: Just drinks. It’s an easier escape if it turns out I’m crazy. 

Vanilla: Good thinking! Lol. Drinks it is. Whiskey Tavern in Chinatown okay? Pretty low key. 

Babe: Sounds good! 7:30?

Vanilla: See you then! 


Pretty typical text convo, I guess. I always prefer bars to dinner on the first date unless I’ve already met him because, obviously. I don’t have time to waste and thankfully I don’t have to rely on other people to eat (no shame, ladies…been there, done that).

So I get to Whiskey Tavern at 7:30. He does not. I sit down with a Guinness for about 15 minutes before he gets there and doesn’t apologize (asshole). I’m going to skip through our conversation. There was literally nothing interesting about this person and I’m pretty sure I volunteered minimal information about myself.

He finishes his beer before I do and he doesn’t ask for another one. Could it be?? A one drink date?? I’m glad we’re on the same page and you think I’m just as boring as I find you!! He pays for our drinks and turns to me.

Let’s head over to the Pho place. My reservation’s in 10 minutes.

Oh, we’re going to get dinner?  I specifically said JUST DRINKS.

Yeah, this place is so good. And cheap. 

Okay, okay. I could have held my ground and been like, um, bye. But it was cold, and Pho sounded amazefest. So I stood up to go. And he immediately regretted it. He did the up and down and I could sense the disappointment. He was about three inches shorter than me (I’m 5’6″) and I was wearing heeled booties. Apparently he’s not super comfortable with his height.

So we got Pho and it was SO good. And the conversation was non-existent. And I was being a childish betch and didn’t even touch the check because I was minorly irritated that he made dinner reservations when I explicitly said “just drinks”. And he was real awkward about paying. And then we walked to the train. And then we parted ways. Riveting, huh?

But every experience can offer a lesson. The lesson here was that Whiskey Tavern is near a dope Pho place.

Love always,

Art Babe



Dating, Dating Challenge, NYC, Online Dating

The Architect that Wasn’t Really an Architect


After multiple swipes and flaccid conversations over text, I finally settled on “The Architect”. This was going to be date No. 1. This was going to be THE date that will launch me into an unexpected journey of self reflection and realization (cue in dramatic music and sounds).

Fast forward to Friday night and I find myself making plans with friends to meet up after this date, and assuming that I will need a valid excuse to leave early. As I turn the corner to enter Hot Bird’s patio, I see a tall and lanky figure come towards me. He mutters my name inquisitively and I awkwardly agree, “yup, are you (insert anonymous name here)?”

The ungracefulness of the hug that followed was tragic. He was tall… REALLY tall. So tall, that as he wrapped his arm around me, my head nestled neatly into his armpit. He had glasses and, from what I saw, a good sense of style. Though he carried a slight sense of arrogance, he was pleasant.

The conversation started with the typical interview questions: Where are you from; How long have you been here; and What brought you to the greatest city in the world? For the sake of carrying on the conversation, I must admit that I was probing. There were a few moments where I stumbled on my words because my eyes began to wander from boredom. Unfortunately, I have yet to master the I’m-very-interested-in-what-you-have-to-say look. My eyelids embarked on a difficult task to stay open and the bags under them enlarged as I squinted to stay focused.

I was fighting an internal dialogue, “Do not lose eye contact. Stay focused. Maybe you should leave now? I wish I could teleport out of here. How do I end this conversation? What did he just say about not being an architect?”

I’m sorry, what now?

Backtracking a little bit, I politely asked him to clarify.  He explained that although he told me that he was an architect when we were texting, he confirmed that he was not actually an architect. The nature of his work allows him to interact with these professionals, however, he himself was not one.

I suppose that’s the beauty of tinder – you can fib about yourself to make yourself appear more interesting. Look, if it means gaining you a swipe then I say – WHY THE HELL NOT?


XXX Babe

Dating, Dating Challenge, NYC, Online Dating

Fries for Dinner

Screen Shot 2017-05-15 at 10.03.40 PM.png



Date #1

I purposefully walked around the block 3 times.  I was avoiding being early which for some reason I’m usually fine with doing. After all, I did ask him out about 4 hours ago and he said yes. Okay, first step completed. But now you have to actually go on the date! Darn. This was going to be fun I told myself. Sure…I took one more lap around the block to relax.

We ended up arriving at the bar at the same time so I avoided that “What’s he look like again?” situation. He was lovely and had such great energy. I noticed the bar was filled with dates. New York City at Happy Hour can really fee like a dating zoo. We couldn’t even find a seat. Welcome to Mating Season.

So we moseyed to the back and found a couch that engulfed me. There was quite some distance between us. In fact, at one point he was closer to another couple that ended up sitting next to him. Halfway through the date I realized I had no lunch and those drinks were going through me fast. A few thoughts starting rushing through my head: Am I ready for this challenge? Are you jumping into it? Can you take one more Monday cocktail?

I saw a familiar face in the bar and winked at a fellow Babe that entered with her date. Right on time. We planned to meet up at the same bar actually. At least this way, if anything crazy happened I could latch on to her. It was quite comforting knowing she was only a few feet away. But my plan backfired. I became more nervous when I saw her. What if I run into her and blow my cover? So now I was on the ultimate first date and had to play James Bond? Multitasking was never my strong suit.

Back to the date: we chatted about family and travels. It was nice and smooth. Everything a first date chat should sound like. We decided to wrap up the night with a plate of fries talking about what shows to watch on Netflix. Always safe. But then my friend walked by and I couldn’t help but smirk.

It was getting late and I realized I should probably wrap up my night. With a quick hug I sauntered to the subway and organized my thoughts. I got my first point, but was I capable of getting more? Date #1 was charming, but where was the spark? I came to terms that maybe the girl who just got out of a relationship may not be ready for something as adventurous as a dating challenge. Or maybe the challenge will help me find what I was looking for? Well, I guess there was only one way to find out. I’d have to trudge along and see what treasures I’d find on this map.

Halfway through my sleepy subway ride, I ran into a guy I matched with months before the challenge. “Hello,” he said. Maybe this was going to be a lot easier than I thought.


Tea Babe

Dating, Dating Challenge, NYC, Online Dating

“I Can Almost See Your Boobs”


Date #1

A dive bar on the UWS. Public, casual, and taking cues from Olivia Benson, safe for my debut on the online dating scene. And it’s trivia night. So even if this guy’s a dud, I can exercise my Leo competitiveness. My outfit was minimal- black pants, black booties, and a black v-neck sweater that hit just about mid-chest. A bit of mascara and voila! Cute and dive bar-y.

On the way over he texted.

What can I order you? 


Oh. You don’t want to see a cocktail menu?

Nope. Just a Guinness. Thanks!! 

Walking into the bar, I realized I didn’t reeeeaaally remember what he looked like. It’s Day 2 of the challenge and I Bumbled 10 faintly memorable people attempting to sound genuine when they asked why I was so adamant about drinks tonight. I have a crazy busy week ahead of me and this is the only night I can meet! I just prefer meeting in person- texts aren’t my thing 🙂 Is that weird? I probably sound aggressive. Or like someone who would turn into a crazy girlfriend. Turns out, crazy attracts crazy. 

The bar was well-lit and crowded. Found him. We introduced ourselves and, wait, does he have an accent? Yup. A Liverpool native who spent a big chunk of his childhood staying with his grandparents on a (beautiful) beach in Israel. AND he had a solid job in finance.

Cute. Foreign. Clean. Point for me!

Have you ever been on a date where you waste your precious time sitting across a table from someone who masterbates his ego all night? This wasn’t one of those dates. The conversation was great. No awkward silences, nice flowy conversations, thoughtful questions. Also, the trivia happened to be mostly sports-related so we had a few laughs talking about all the things we didn’t know about American sports, or sports in general.

The night was winding down. Neither of us had hinted at a second date but it was obvious we were enjoying ourselves so I knew it would happen. We left the bar and, still standing out front, I pulled out my phone.

I’m going to call a car.

Why? My apartment’s just around the corner. *wink*

Ugh. No! Just stop! Did he actually just wink at me? We had such a nice night, don’t start being an asshole now.

I need to head home. I had a fun night though. 

Me too. You look really nice tonight. That outfit’s really cool- I can almost see your boobs in it.

What. The. Fuck. I just stared at him.

Yeah, I knew you wanted me to look at them. You kept leaning over the table and I really liked it. You sure you don’t want to come over?

I’m sure.

Oh, thank God. That was the fastest pickup ever. I’m b-lining to the car and of course he tries to be a gentleman and hold the door for me, but it’s too late for that, dickwad!


You definitely need to call me soon. We’re going to have A LOT of fun together. I mean A LOT of fun. 

I pulled the door closed just barely missing his head. Damn, I should have closed the door harder. And that was it. Point numero uno for me. I’m in the game now, no turning back. I was just hoping it was all uphill from there. And it kind of, sort of was.

Love always,

Art Babe