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: Traveling Salesman

December 2018

So I had my first post-divorce fuck. It was…. ok. Lackluster. Whatever, I didn’t cry and it wasn’t terrible, so I’ll put it in the win column.

After I had put the kids to bed on a Thursday night, it was “my” night to go out (some terrible fucking system that me and the ex came up with where we could go out while the other one stayed home with the sleeping kids). I was just swiping on Tinder and came across this tall, blonde man who seemed cute and could laugh at himself. I read his profile and realize he’s a salesman based out of Seattle.

Hmmm. How do I feel about one night stand with a traveling sales dude? Well, fuck it, he may not even reciprocate my feelings of attraction, so what do I have to lose?

So I swiped left and left it at that (If this were Bumble, I’d hit you up, but this is Tinder. Unless he’s hotter than Hades, I want him to message me to show he’s remotely serious).

To my surprise, he messages me almost immediately.

He seems super normal. Just a dude, who happens to be in my city, doing his thing. He’s bored. I bring up the fact that my bestie lives in Seattle. He says it’s overrun by weirdos, but overall it’s pretty cool. I mention I plan on visiting once life settles down after my divorce. He comments that it’s probably best for me to get divorced bc I’m hot. Then he makes the remark that it’s his last night in town.

Oh how convenient.

We flirt a bit more, but I’m pretty sure I’m going to stay in for the night. Then he offers just to grab a beer and says he doesn’t want to come off as creepy.

Ugh. Ok fuck it.

So I meet him out at a Chili’s of all places. Because it’s late and a Thursday and despite him being in a major city, his hotel is in a weirdly remote part of the city. So here we go, to get lit at Chili’s on a Thursday.

Y’all. Chili’s bar is where it’s at. They hook you up, FR. You can double your alcohol for 75 cents.

Well, guess where this story is headed.

We get wasted at the bar, and laugh about stupid stuff, and he calls an Uber to take us back to his hotel. When we get there we drink and chat a bit more and he tells me how plesantly surprised he is by how fun and cool I am. We talk more about our lives, my divorce, his regrets over not having children at this point in life…..

And then suddenly my clothes are on the floor.

We move to the bed and before I know it his hand is over my mouth because I’m screaming so loudly in ecstasy. He shushes me and continues to take over my body and I feel things I haven’t felt in years. I lose count of how many times I orgasm.

We fuck 2 more times before we realize it’s 3 in the morning. He has a flight to catch and I have to take children to school in less than 4 hours.

He helps me find my clothes, and calls me an Uber back to my car at Chili’s. We exchange numbers and he walks me outside and makes out with me until the driver arrives. He tells me to call him whenever I come up to Seattle, and we say goodbye.

The next day is rough. I’m luckily not hungover, but super sleep deprived, and the ex-husband is furious that I was out all night and he had no idea where I was. I don’t care.

I realize I’m walking funny. The insides of my thighs are bruised. I text him and tell him that I’m clearly out of practice, but I still feel amazing. He tells me I just need to get fucked well more often. The weather is turning nasty, and I secretly hope his flight gets cancelled. But in a few hours, he’s back in Washington.

We don’t chat again.

…..Until last week, when I made plans to go visit my bestie for Memorial Day. I text him and let him know I’ll be up there.

Salesman: You gonna be in Redmond?

Me: Yeah, that’s the plan

Salesman: Sweet. Well, let me know.

We’ll see what happens in May….


2nd date: Not yet…

Sex: Yes

Ghosted: No. Responded very promptly even though it’s been almost 4 months.