Date file NY Edition: The Professor

March 2019

So the St. Patrick’s parade was meh.  The lawyer was nice, but the sex was meh…. And so on actual St. Patrick’s day (a Sunday) I was just kinda feeling meh.

I actually don’t remember much of what we did that day, but given that it was a Sunday, sister was not interested in going out for the evening.  She told me, “you do you, boo” and so I chatted up a guy from Ireland. He suggested an Irish bar (how appropriate). It was pretty early in the evening, so I figured it wouldn’t be too crowded.  I thought there had to be something lucky in kissing an Irish guy in an Irish bar on St. Patrick’s Day.

Now, I don’t know if you can tell or not, but I give zero fucks about doing things alone.  I went to the bar, grabbed a seat that had an empty one on either side of it, and ordered a beer.  As I was drinking and scrolling through the various dating apps, I realize he’s at least 10 minutes late.  He makes an excuse but insists that he’s coming. Whatever, I’m from out of town, and I’m still talking to other dudes on these apps.

I get hungry and order a burger and another beer.  Continue talking to other dudes. Realize 30 minutes have gone by.  But he’s still texting me saying he’s coming.  

Hmmm.  Fine, I’ll stuff my face while you do or don’t come.

Finally after I finish my food, I think, “fuck you, man” and unmatch from him.

All the while I’ve been talking to this guy who’s a professor at a local university.  He finally asks me what I’m doing tonight.

“Well, I was going to grab a drink with someone, but I believe I’ve been stood up”

“What?!  On St. Patrick’s Day?  You’re alone in a bar on St. Patrick’s day.”

“It appears so, yeah.  So I’m gonna go back to my sister’s”

“Wait!  Where are you?”

I give him the deets.

“I can be there in 15 minutes.”

“Dude, I’ve already been here for over an hour by myself”

“No, I promise, I’ll be there soon.”

“Ugh… ok fine.”

He shows up.  He’s wearing a crisp, black suit with a black tie and freshly shined shoes. He’s got on a thick wool pea coat and scarf that looks like it’s made of cashmere.  He’s bald (not usually my type), but the intentional bald and he pulls it off.  

“Well, I feel like a schmuck.  Where did you just come from?”

“I had a donor’s dinner I had to attend”

“Oh well aren’t you fancy?!”

And he gives me some sort of exaggerated eye roll and I can already tell we’re going to have fun banter.

As I get to know him more, I find out just how fucking brilliant he is.  Two PhDs. We have a lot of common interests in psychology and higher education.  He’s one of the few men I’ve been on a date with who I can tell is clearly smarter than me.  I ask more about him and his education, bc he’s truly fascinating to me, and he gives me shit, asking if he’s on some type of interview and if he should have prepped his CV before coming over.


I give him my whole backstory of the cheating husband and being fired from my job and just enjoying being single.  He doesn’t want to hear about the husband. He doesn’t want to hear about the job. He just wants to talk about fun things.  Not in a “fuck off, I don’t want to hear your sad story” kind of way, but in a “let’s enjoy this moment here” way. I can tell he wants to just be flirty and fun, but also takes himself quite seriously, so I keep drinking and become more playful.  I lean in to kiss him and he stiffens up.

“Not here. That looks sloppy”

“OH!?  Well you’re the one talking about anal sex in a bar!”

“SHHHHH What is wrong with you?!”

“Just saying, I think it’s interesting you’re willing to ask me about pegging in a bar, but I can’t give you a kiss.”

“I want to take you back to my place.”


He orders us an uber and takes me to his apartment.  I can tell how irritated PDA makes him, so I do it as much as possible just to give him shit.  It’s a new building, and there’s still a lot of construction. He quietly says hello to the concierge, and I say in my thickest Southern accent, “well, HEY THERE!  How’s your evening goin’??”

The professor shoots me a dirty look and pulls me into the elevator as I giggle.

When we get to his apartment, he immediately starts to take off my clothes.  I’m still trying to get oriented to the space. New York is so weird. He clearly is pretty successful, and he has basically an efficiency apartment.  All one large room. Kinda like an extended stay hotel room. Apparently I say some comment to myself in a snarky manner and he again gets offended by my observation of having an efficiency apartment.  I tell him not to get his panties in a twist and chill TF out.

The sex is pretty great.  Our banter has made good foreplay and apparently he loves to eat some pussy, so he sits me on his face.  As I grind down on him we both moan and when he comes up for air he says, “What is wrong with your husband?? I cannot believe that fool left you!”

And suddenly it’s like someone threw me into a frozen lake.

I’m trying hard to not let the words shake me or prevent me from having my fun.  I can’t even remember if we finish. The next thing I remember is getting dressed, trying hard to push back tears.  Him asking me what was wrong. Me trying to lie, badly. 

He knows he hit a nerve.  I’m sure he was just trying to be complimentary.  To tell me how great I am in the sack, and that my husband doesn’t know what good he threw away.  But it just stings. Because it just makes me feel like no matter how good I could have been (at anything, not just sex), it wasn’t ever going to be good enough for him.

When I’m done getting dressed, he asks me how long I’m going to be in town for.  One more night. He tells me he wants to see me again tomorrow if I’m free. I think I’m free?  I’m not sure.

He calls me an Uber and I go home.  The next day, we chat a little bit, but we can’t make our schedules coalesce.  So I never see him again.

Date File NY Edition: The Lawyer

March 2019

Y’all, life has been keeping me busy. So I apologize for the delay in writing… hopefully I’ll have a few things to say tonight and we can keep moving…

So if you’ll recall, I was in NY for a last minute I-feel-sorry-for-myself-because-I-just-moved-out-then-got-unfairly-fired trip. When I booked it, I really had no idea that I had booked it over St. Patrick’s Day. So being in the city, without children, and single during a major party weekend made my college hedonistic self come out to play.

I met a lovely lawyer on Bumble. We kept the conversation going and he said that he was game to go to meet my sister and I at the parade. Now, where I’m from, St. Patrick’s day is really just Green Mardi Gras. LOTS of drinking, beads, and general debauchery, but only wearing green. Came to find out in NYC, it’s legit about Irish pride. Who knew?! So after a chalking up our hair green and putting on every green garment we could fine, my sister and I headed out and watched Irish clubs with their banners waving, high school marching bands playing, and little Irish dancing girls in their Irish costumes. I didn’t really see any floats or people falling all over each other drunk, or any of the other bullshit I typically see at my local parade. Whatever. So the lawyer texts me and finds where we are. He also had never been to the parade and seemed about as lukewarm about it as we did. Afterwards though, he recommended a nearby Irish bar.

Approximately half the city was there.

We squeezed through the patrons and he bought me some cider. When we talked we had to touch because of how many people there were and how loud it was. As we drank, everyone got louder, and we stood closer, our lips touching each others’ ears when we talked.

Sister was very tolerant of it all.

We all eventually decided we were legit hungry, so we left that Irish pub for something with real food. Weirdly, we found a German restaurant nearby that was also crowded, but we could at least get a seat and food with our adult beverages. We ate delicious German food and talked about travel (my sister had lived in Germany for a year) and drank more beer. The restaurant began to fill with New York’s finest, and I got to wear one of their white caps while I continued to become inebriated. The lawyer picked up the tab (again… he got it at the bar too), and then we tried to find another venue for some dessert.

We came upon a 50s style joint and ordered adult milkshakes. We split it and the lawyer and I continued to get cozy. At this point my sister “had a headache” and said she was going to head out. She told me to be safe and text when I was on my way home.

As soon as she left, the lawyer leaned in and we began to kiss in the restaurant. A few minutes later he asked if I’d like to go back to his apartment downtown.

Um, yes please, Mr. Successful Lawyer. I’d love to see your high rise downtown NYC apartment.

He hails us a cab, and we continue to make out the whole way to his place. I realize how drunk I am and that I really have no idea where I am. I snap a picture of the address when we pull up, and send it to my sister as he’s paying the cabbie.

We fly up to the 17th floor and he takes me to his apartment. I walk in and am awestruck at the view. The sky scrapers glitter in the darkness, and I snap another picture to send to my sister while he’s in the bathroom.

I realize there are several doors. That’s when he lets me know that he has roommates.

Ah, of course. He’s only like 29. Doubtful he’s got a view like that in an apartment by himself. Even with his fancy-pants job.

He takes me into his bedroom and we quickly get down to business. Something about the way this is all happening just feels… off. He’s not creepy, or rude… I’m just not really feeling this vibe.

I get off (because I always do) and then find that no matter what trick I try, he doesn’t seem to be able to go. Eventually I become too dry for things to be comfortable, and we give up. He insists it’s fine. I’m less thrilled by the final outcome.

He looks tired. I say that I should probably get home to my sister and ask where the nearest subway stop is. He looks at me like I’m crazy.

“You’re not taking the subway home, alone, with all that shit going on in the city. Especially because your sister lives at the top of the island. It’ll take forever for you to get there. I’m calling you an Uber.”

He takes me back down to the lobby, waits with me for the Uber, kisses me goodbye, and that’s the last I see of him.

Date file NY Edition: The Irish Boy

March 2019

What does one do when they find themselves newly divorced and newly unemployed? Well, I don’t know about you, but I book a trip to New York City for a few days of hedonism.

Sister lives in the Big Apple at the top of Manhattan. Like, she’s practically in the Bronx. I fly in on a Wednesday afternoon and being a normal work day for all other humans, Sister is obviously doing her normal adult work life. Like many people in NYC, she is also a creative, so she has rehearsal or so other such thing that evening. So I’m left to my own devices for my first day-ish in the big city.

I make my way down to Sister’s work to let her know I got into town safely and to get the key to her apartment. I meet her boss who literally lives in an apartment overlooking Central Park. It’s like I’m in the Time Zone. Nothing makes sense. People are reminding others to pay the Chanel invoice, discussing how tired this other person is due to just finishing styling some A-list celebrity for the Oscars, and paying some Uber driver $500 dollars to drive back from Brooklyn to return the iPhone Boss Lady left in the backseat. It’s a totally alien environment.

All the while I’ve been chatting with a guy from Jersey who has the most fucking Irish name I’ve ever heard. I assume he’ll be going to the St. Patrick’s Day parade.

“Oh fuck no. I don’t go to that shit. I will be in the Poconos. My extended family throws the most ridiculous, multi-block St. Patrick’s Day party where they all pretended they are not raging alcoholics. I am leaving tomorrow morning before the weekend hits.”

“Oh. Well, I’m alone tonight. Shall we hang out?”

“Sure. Can you make it to Hoboken?”

“Uh….. sure….”

And then the SexySuburbMom becomes the LostIdiotGirl. If I can stick to the subway, I’m alright. But this involved a ferry and a bus. Eventually I found my way there. I knew I was in the right spot when I saw more white people in one place than I’d seen anywhere else in the city.

When I arrived in Hoboken, Irish guy was there to greet me. We walked over to a not insanely crowded bar as it was now happy hour and had a couple pints. We talked more about my situation and I learned more about him. We’d been talking for a couple days, but I got to know more about him and his life across the river from NYC. We talked about how shitty and stupid online dating was, but it was pretty cool for people just looking to meet up with other people in a new city. After a couple beers, I decided I didn’t want to get really wasted with a stranger in a strange city, so I asked for the check and said we should walk outside.

We decided to go walk along the waterfront. As we looked across the rive to the skyscrapers, I asked what it was like to live there on 9/11. He told me what it was like to watch the towers fall on his second day of his junior year of high school and have friends worried about their parents’ fates. I talked about my experience 1500 miles away and tried to relate. He convinced me I should visit the 9/11 Museum, but he had absolutely no desire to go there ever again.

As we were talking and walking, I eventually realized we had wandered into a more residential area of the city.

“Where are we going?”

“Oh, back to my place. Is… that ok?”

“Oh. Yeah. I guess.”

“We can go somewhere else if you want. I was just going to grab my cigarettes”

“You smoke? Gross”

“Yeah, I know.”

When we walk into his apartment, I noticed a large tank in the corner. He tells me that’s his bearded dragon, Idris Elba.

“Why did you name him Idris Elba?”

“Why would you name a bearded dragon anything else?”

He smokes a cigarette outside and I play with his giant labrador. When he finishes, he pops a stick of gum and kisses me. He’s a good kisser, so I go along with it and we move our make out session into the kitchen. He lifts me onto the countertop and slides his hand up my shirt. I remember he mentioned a roommate, so I request we move to a more private place in case she returns. We make our way towards his room in the basement.

Now, in my part of the country, basements are rare. So this kinda freaked me out. And lets face it, I don’t really know this dude, so that kinda freaks me out. But I know how to take care of my own, so I choose not to freak out.

We have a good time. Better than I thought we would. Eventually he lets me know that a friend has to stop by to pick up something. Nothing to make you feel super awkward like meeting the friend of a stranger knowing that they most likely know we just had sex.

His friend is very normal and quite nice and jokes around for a bit before leaving. I realize the sun is setting and I should make my way back to the top of Manhattan. While I’m starting to gather my things that I had left in the kitchen, he kisses me from behind. Before I know it he’s fucking me from behind on top of his dining room table with my panties around my ankles. We go quickly, because we still don’t know when the roommate will walk in. Once we’re finished, he walks me to the end of the block and I tell him I can make my way back to the subway on my own. I tell him to have a good time in the Poconos and he tells me to be safe partying in the city. 10 minutes later he texts me to let me know that we narrowly missed his roommate walking into the house.

To my surprise, he continues to text me throughout the weekend despite knowing we can’t really hang out at all. He’s funny and easy to talk to. We try to get together one more time before I head back home, but the stars don’t align. He asks me to let him know the next time I’m in NY, but I let him know I will have a child in tow. I tell him not to hedge his bets on me, but if we can make it work, that’d be cool.

Over the next few months, he texts me randomly and I text him randomly. He kinda turns into a confidante of sorts, and I am for him too.

Recently, I’ve met someone. It’s honestly the main reason I haven’t written in a while. A few days after I met him, Irish guy texts me. I tell him I’ve met someone.

“Then why the fuck are you texting me back, crazy face?! Go be with him!”

“Ha, fair point. Thanks, Irish Guy. You’re a good dude.”

Honestly, I wouldn’t mind talking with him still because I’m the kind of person who can have a sexual thing with someone and if it doesn’t turn into something more, I can flip it into a platonic relationship and never look back. But maybe he’s not. And that’s ok.