I’m Sorry, Vajay


Date #10

This one is painful.

It’s Friday night at 7 and I sat down at a bustling Harlem dumpling spot with the cutie patootie software engineer from Date #8. Dinner was good- it took a while to explain that I didn’t want meat or eggs with any of my dishes (so high maintenance)- but the veggie dumplings and steamed veggies were delish. After dinner, we couldn’t find any bars in the neighborhood that weren’t loud or expensive so we called it a night and started heading to his place.

I should have known this wasn’t going to end well when he insisted on catching the subway for one stop.

Why? It’ll take longer to wait for the train than it will to walk. 

It’s cold though. And it’s kind of  a far walk.

11 streets and 2 Avenues? 

Yeah, let’s catch the train. 

But that’s not efficient. 


Should have known. Should. Have. Known. There are few things that annoy me more than inefficiency, but it was the weekend! So I was trying to be cool and let loose.

Let’s skip to the juicy stuff…or rather, the not-so-juicy stuff if you get my drift.

We get to his apartment and his roommate is in the kitchen so we make a sharp left straight into the bedroom. He turns on Real Husbands of Hollywood insisting that I’ll think it’s hilarious. Half an epi in, we start making out and it was okay but 30 seconds later BOOM! He goes for the zipper.

Do you have somewhere to be? Are you late for something? Jesus. Slow down.

Apparently he didn’t understand how this was supposed to go and I wasn’t in the mood to educate this kid on how to have proper sexual relations with a woman. So I redirected him back to my lips and told him to back off down there. But it didn’t get better. The kissing was sloppy and saliva-y. At this point I was over it, but the show was funny, and this guy was cute, and I wasn’t about to leave without getting any D. I mean I was already there and had already used up some effort on him…how bad could the rest be?


It started getting heated and then- again with the horrible transition- got up and grabbed a condom.

Oh, no. Put that away, I’m not ready yet. 

Oh, uh, okay.

So he came back and rubbed around for a bit but it was pointless. He was lost down there. So condom it was. BUT THEN HE CAME AT ME WITH NO LUBE. Jesus. I had verbalized TWICE that this was the largest penis I have ever experienced in my entire life and he didn’t think to lube up? Who is letting him fuck them without lube!?? Even if I was juiced to the max, I doubt that would have been enough.

So I had him turn around again, get some lube, and THEN approach the golden chalice that is my sacred lady bit. But it was bad. Every position was bad. When I got on top and told him to literally just lay still, he couldn’t follow directions. So it was over. I got up unsatisfied and went to the bathroom to find blood dripping down my leg. And it wasn’t period blood. My vajay was broken and in pain.

And the bleeding/throbbing continued through to the next night when I went out with Babeland. Dancing with a sad punani isn’t fun. But then I started thinking, perhaps this guy has never had a relationship before. Maybe he’s never been taught how to properly wield his sword because his previous trysts have been with one night stands or flings who don’t have the time/want to teach him. Or maybe he watches wayyyy too much porn and he’s single because he can’t figure out sex irl. Or maybe he’s overly sensitive to criticism and is a horrible sex student and dumps anyone who tries to suggest something new in the sheets. So many possibilities. I could write an entire fictional blog on the sex history I imagine for him.

But the most important part of the Babeland Challenge is to learn- learn about ourselves and learn about the other people in this metropolitan playground. Lessons learned from this date: 1) Big dicks are nothing to joke about. They are serious business and need lots of mental and physical preparation and probably a lot of practice. 2) Sex injuries not funny. 3) I’m too old for guys my own age. Let’s try upping my Bumble age range from 24-35 to 30-35 and see how that works out.

Love always,

Art Babe




Not Sam Smith


Date #9

I had never really considered having a one night stand. All  those STD pictures from high school combined with watching too much SVU has kind of turned off the idea to me. Plus I like to cuddle without any awkward small talk. And I don’t like bringing people into my bed unless they shower first. And I don’t like getting it on in dirty boy apartments. But at least I’m not high maintenance….

Let me set the scene for Date #9. Monday night. There’s a snow storm a-comin’ and schools are cancelled tomorrow (which means no work for me!). Treating this Monday like the Friday it has become, I agreed to go on a date at 11pm with a guy who had a really cute bulldog in his Bumble prof pic. He got off work at the hospital around 10:30 and asked to meet me at a cozy wine bar close by so he could shower and not be late. My first thought was: aww that’s nice of him to shower first. And then I was like: Are you fucking kidding?? Of course he should shower after being in the nasty ER all day. Set your standards a little higher, betch. 

Our previous day of texting had been hilarious but in a friendly, not flirty way. And, I know this sounds bad, but I wasn’t super into him like that. I just figured I’d get a point out of the snow storm. When we met, we got along instantly. The conversation flowed, we had similar senses of humor, and we laughed until 2:0) in the morning. But I never got the feeling that either of us were even vaguely romantically interested in each other. Just cordial.

After a bottle of wine, we got up to leave. He helped me put on my coat and turned to me.

The storm isn’t here yet- if you want to come over I live just 2 blocks away.


And that’s it. THAT’s how my first one night stand happened. Are you breathless?? Begging for the dirty deets?? Yeah, I didn’t think so. It was so casual I almost didn’t realize I was about wonder into uncharted sex territory.

We wandered through the UES streets just as they were collecting a thin layer of snow, awkwardly stepping so we wouldn’t slip. He was a good 4 inches shorter than my 5’6″ frame and at one point he tried putting his arm around my shoulder. It just didn’t work. With the extra cautious walking and the height difference it was just dumb. So he retracted his arm and we approached his apartment.

His dog was cute. And his studio was okay. Pretty much exactly what I would assume every 28 year-old doctor’s apartment looks like: large and empty. We made out for a hot second and then got it on. It wasn’t good. And then I said bye to his bulldog and left.

That was cool. Maybe I’ll do it again sometime. Maybe not. One of the perks of a relationship is getting better at sex together. Unless both people in a one night stand are incredible sexperts, I’m not confident that I can have great sex on a one night stand. Not my cup of tea, I guess.

Love always,

Art Babe


Sound the Siren


Dates #6-8

I’m getting better at this so let’s speed things up a bit, shall we?

Date #6- The Harlem native again. We went back to the hot dog place (not on trivia night) and had a great time. I have a good feeling about this guy. A feeling that this might last a while. We’re not afraid to laugh at ourselves, or each other. And he made a couple references to things we should do in the future. Stay tuned for a third date in the near future.

Date #7- I have nothing to say about this. My brain kept telling my legs to walk out of the bubble tea place but my heart felt bad for being so over it. So I stayed for 45 minutes and had a nice conversation. He texted me the next day. I didn’t respond.

Date #8-

This one is worth talking about in detail because HUBBA HUBBA. This man was gorgeous. And his smile…*drool.

Date #8 was just 2 blocks away from date #7. Yes, I planned that. But because date #7 ended early, I got to the bar early. I ordered a couple Guinnesses and some fries before he got there (on time!) and he did a subtle double take when he noticed I’d been there a while.

Oh, I’m sorry I’m late!

You’re not late. Want something to drink? 

He was so into me. Not to be like that, but hot damn. We were a good pair. Equally hilarious (if I do say so myself) and both with interesting family histories.

He was born in Germany, grew up in a super white part of Florida, had a punk rock band in high school (the pictures of him rockin’ a giant afro AND fall-out boy style outfits AND being so lanky and awkward and skinny are just too amazing for words), and moved to NYC to be a software engineer. He was brand new to the city, so I knew to be cautious. It’s no secret that online dating is a great way to meet people/make friends when you’re fresh to New York and I wasn’t really looking for that casual stuff. Yes, this was just a silly challenge and I wouldn’t have downloaded all these dating apps otherwise, but I was still looking for a real relationship.

We could have talked for hours but I was going to be late for a movie with the rest of Babeland so I paid the bill. He was flustered.

Oh, what? No, I want to pay for it. I- I didn’t know you had a tab open.

No, it’s cool. I was here for a while before you anyway. 

Okay, well I’ll get it next time. 


And he walked me to the train station and waited on the platform with me. This is when things got weird. He stood in front of me. Face to face, almost chest to chest. On the platform. Not okay. Everyone faces the tracks on the platform. That’s just how it is. Now I feel like my space is being violated.

Stand next to me. If you stand like that you can’t see the train.

But I’ll hear it and know it’s coming.

What? No. Just stand over here. 

We held hands but he tried holding both of my hands at the same time…while standing next to me. YEAH. Think about that for a second. It was so awkward.

My train finally arrived and I kissed him goodbye. Up until the train station it was great. Then it was just so wrong. I had to digest it for a bit but I was down for a second date. We were an intriguing possibility.


Love always,

Art Babe



Tuesday Night: Part II


Date #5

It was 11:00 by this point, just about booty-call time. And I was in a car heading to a speakeasy with the Canadian engineer from date #2. He had just left dinner with his friends and was definitely buzzed when I showed up (I wasn’t the first to get there this time!).

Let me back up for a second. I wouldn’t typically agree to rage on a Tuesday night, but he was heading to Israel for three weeks with his grad school for some abroad work. If I wanted to see him before he left (and get a point for it), it was now or never.

The alcohol really loosened him up. He was still gentlemanly and sweet but he was much more animated and almost feminine during our discussions. I was into it. Too into it. Two gin martinis into it.

We closed out the speakeasy and tried to hold ourselves together as we wandered out the front door. We both lived north so we started heading in that direction. And we just kept going for 30 blocks. Two long walks in one night!? I was on a roll. Legit feelin’ myself after this monumental night in my dating history.

We got to 110th street and I held out my hand for a cab. Before getting in, I turned and wished him a good trip. He said he’ll call me when he got back. And I rode away.

No kiss. No hug. Just a wave. And that was that.

He never reached out. I never reached out. Just two great dates for the archives. I’m starting to understand the fun part of dating.

Love always,

Art Babe


Tuesday Night: Part I


Date #4

I don’t know if it was the spring air or the fact that I sat next to SJP at a Vietnamese restaurant recently, but I REALLY got into the game Tuesday night. I had not one, but two great dates. In one night! Okay, okay, so maybe you don’t find that particularly exciting, but boy, oh, boy, do I.

The first date started as all my dates have so far…I was five minutes early and he was annoyingly late. We were meeting at a casual place on W 116th and his excuse was that he got on the express train and had to double back and of course, the trains were delayed. I’ll give him the benefit of the doubt…but he was born and raised on W 130th so that was a dumb mistake. *eye roll

We walked into a beer and hot dog place (vegan hot dogs!) and it was packed with Columbia students doing trivia so we popped into an intimate bar with super hip cocktails a few blocks away.

This guy was cute. Kind of nervous- or was he drunk? Mmm, no, just nervous. I would be too if I was just breaking out of a four-year relationship with my live-in gf. We laughed and talked about where we grew up and ate roasted brussels sprouts. And we drank. We drank several cocktails.

As things were winding down and we (he) got the check, and he offered to walk me home.

Oh, you don’t have to. (Because I have another date right after this)

No, it’s fine. I love walking around the city.

You sure? It’s about two miles away. 

Yeah, of course. Let’s head out. 

So we walked.

I’ve only walked around the city on a date one other time but this was my best date walk yet. He pointed out some important neighborhood buildings. Told me some funny stories about his childhood when we passed his old playgrounds. And had a lively discussion about public housing and how to make the buildings and space more efficient and less oppressive.

In the end, it was a great date. As we were about to part ways in front of my building, he asked to kiss me.


What? Oh, I’ve never- I wasn’t expecting you to say that.

Sorry, I don’t kiss on first dates.



Okay. Well…I had fun. Let’s do this again?

How about next week? 

Okay, sounds good. Night. 

And I stood in my doorway watching him ride away in a cab. When he turned the corner, I got out my phone and called a Lyft back to the West Side.

To be continued…


Love always,

Art Babe


Does He Exist?


Date #3

Well the answer to that question is yes, but not really. Confused? Let me explain: He was one of the first guys I swiped and not going to lie – he was pretty swoon-worthy. I was excited until I realized how difficult it was to plan with Mystery Boy. Eventually after many failed attempts to meet live, we finally met up at an oh-so-romantic Meatpacking lounge (Queue eye roll). But to be honest, the night wasn’t horrible. He was very charming.

Afterwards, we planned to meet that Saturday. It included extravagant dinner plans where he was meant to “pick me up” (what does that mean in NYC?) but then he never came. No cancellation. No call. NOTHING. I get it we all have things to do, but it takes about 2 SECONDS to send a text (haven’t timed it, but I’m assuming). Fine, he’s not my boy, but I couldn’t help but wonder what happened. I replayed a few scenes of him getting aimlessly lost for a few days in Manhattan which isn’t plausible since he’s from New York….Basically it was as if I was talking to a ghost. Pretty intriguing. Bumble profile – deleted. Texts – not delivered. Calls – straight to voicemail. At some point, I put my detective hat on. I just wanted to know if was okay! Spoiler alert: he was doing just fine.

Needless to say, we all know how this story ends. He texted me a month later, we planned a dinner, he cancelled and then the we ended with the cherry on top of a “Hey” text. Goodbye, Casper! Forever.


Tea Babe