top of page

My Seeking Arrangement Date That Went Terribly Wrong

Money can't buy you love, something I began to learn years ago when I joined the dating app Seeking Arrangement, a "sugar" dating site.

Hundred Dollar Bills In a Jar on a Table
Money Can't Buy You Love

What is sugar dating?

According to Wikipedia:

Sugar dating, also called sugaring, is a relationship of an older, wealthy person and a younger person in need of financial assistance or mentoring, achieving mutual benefits...The person who receives the gifts is called a sugar baby, while their paying partner is called a sugar daddy or sugar momma.

Before you judge me, please allow me to illustrate my fragile headspace at the time.

After spending two decades of my adult existence attempting to live according to society’s wishes (i.e. get married, buy a suburban home, climb the corporate ladder, etc.), I was freshly divorced and completely adrift in my life. 

I had a successful career from the outside, yet internally I desperately needed meaning in my life, but I didn’t know how to find it.  

I felt like I needed some fun, an adventure in life - maybe even to try something COMPLETELY IRRATIONAL.

At about this time, one of my good buddies from college, who was married with kids, told me about this new dating site called Seeking Arrangement.    

In a move which would lead my life in a completely different direction, I followed my friend’s advice and signed up for a $99-a-month paid subscription.


Whenever you initially activate your account, Seeking Arrangement provides a boost to your popularity, so instantly I received a deluge of messages. 

Typically when I used the app, I would begin the conversation by asking the woman where she would like to go to dinner so that we could get to know each other better.

My budget for these dinners was usually $200.

My justification for this expense was that as a foodie, if we didn't click, then at least I would have enjoyed a nice meal and a decent conversation.

Almost immediately, I connected with a woman named Symphony.

Symphony isn’t her real name of course; however, her actual given denomination was also a moniker an exotic dancer would DEFINITELY use.

I started off the text conversation by texting to ask how she was doing, and the following was the response I received, which should have been an IMMEDIATE RED FLAG:

an appropriate text message
Immediate Red Flag Text

You might imagine the confusion and surprise on my face as I read this message.

An experienced dater would have instantly cut and run, but as an online dating newbie, I had NO CLUE as to what I was doing.

Then came the ALL BUSINESS MOVE:

Image of a Text message
Another Red Flag

Ok, so these are two of most expensive restaurants in the entire city, and definitely cost more than I had budgeted.

However, I was a novice and in a move of desperation, I foolishly agreed to take her to the fanciest spot in town on a Monday night.


It was a cold March night in Austin, Texas, and I was impatiently waiting in the dark, wood-paneled bar of the ritzy restaurant Symphony had selected.

Ever since Symphony and I had agreed to meet, my brain had been wracked with second thoughts, which were spinning around my head faster than I could impatiently suck down my vodka martini.

What was I doing? What was I thinking? I can just leave now if I want.

My martini glass was in front of me, and I took another long swallow to steady my nerves.

I'll give her another five minutes, and then I am gone.

Then - right on cue - she walked in.

Symphony had jet black hair, pale milky skin, tattoos all over her body, and a nose ring - pretty much the opposite of my prim and proper ex-wife.

She was clothed (barely) in a black leather dress that fit her athletic 5'4" figure perfectly.

Her four-inch tall Christian Louboutin stiletto heels put her right at eye level with me.

She stared at me intently, and I swear she knew that I was a sugar dating novice by the way I was nervously fidgeting.

There was no getting out of this now.


Amidst murmured gasps of shock from many of the restaurant's patrons, we were discretely escorted by the tuxedoed maître d to our fashionable brown leather banquette in the lavishly-appointed dining room.

I could feel my blood pressure starting to rise and sweat was coming down the back of my shirt as I felt the cold stares of the stuffy elitist diners.

Thankfully, we were seated in the far back corner, out of sight of most of the dining area, and eventually the patrons lost interest in us and turned their attention back to their sumptuous food.

Symphony sat right directly next to me, and as soon as the waiter was gone, she put one of her hands on my crotch.

Seductively and with a bat of her eyelashes, Symphony purred that she was a connoisseur of champagne and caviar...and might we possibly splurge on that?

Laughing uncomfortably and noncommittally, I glanced down at the menu to see that the caviar prices started at $100 an ounce.

My head was spinning, and I came back to my senses just in time to hear the final part of Symphony's speech - this was the point where she asserted to me that we couldn’t possibly start with less than two ounces of caviar each.

Salmon roe and toast points on a white linen tablecloth

In my head, I was doing the mental math calculating that our appetizer course was going to set me back at least $400 - not a good start as far as my budget was concerned.

I was starting to realize this was shaping up to be a VERY BAD IDEA.

Despite her pleas and after I had removed her hand from my nether region, I miraculously persuaded Symphony to forego the caviar and instead settle on a $200 bottle of champagne.

I disingenuously told her that I would be happy to get us caviar next time (yeah right, like there was going to be a next time, I thought).

Thankfully, the waiter appeared in the nick of time, and Symphony ordered lobster for her entree at $72, and I had the duck for $54.

A closeup of a grilled lobster tail presented on a black plate with fancy garnishes
Lobster Tail


Shockingly - as we dined on our exorbitant dishes, and I started to loosen up - we actually did start to hit it off, talking about all sorts of things.

One main topic of conversation was her career.

Symphony had done some exotic dancing at clubs around town and was now a hostess at an underground bottle service nightclub downtown, but she was also an actor in adult films.

I may know as much about porn on the Internet as the next person, but I had no idea about the economics of online erotic content.

Apparently every time someone paid for her movie on the Web, Symphony made $40; it was a royalty check that just kept on coming (literally).

Symphony was exquisitely dressed and with an expensive purse, so I never doubted her for one moment.

During dessert, I casually mentioned that I was traveling to New York the next day, and without hesitation, Symphony said she would love to accompany me.

I had a split second to decide.

I thought back to my overall goal with Seeking Arrangement: my desire to find something exciting (or at least distracting) to help me make sense of my life.

Feeling intoxicated with the mystery of what might be yet to come and in a move totally unlike me that I soon came to regret, I got on my phone at the dinner table and booked her a ticket on my flight for early the next morning.


At the crack of dawn the next morning, we were lined up at Austin-Bergstrom International Airport's Gate 21 .

Symphony was dressed in all black with a large brimmed hat and sunglasses, looking like Audrey Hepburn in Breakfast at Tiffany’s, which was apropos because we were indeed headed to New York City.

It was so early in the morning that people did not even give her a second glance as we boarded the flight.

I slept the entire flight, and when we landed, I had a new outlook on life.

Maybe this is going to work out, I thought. I am in a world-class city with a beautiful and interesting person. How could this go wrong?

We checked into our $500-a-night hotel on Gramercy Park in New York; due to my elite status as a frequent guest, the hotel had upgraded my room.

The room itself looked like the inside of of a glamourous Restoration Hardware store, replete with plush leather couches, expensive chandeliers and new age design.

a lavishly appointed living room at the Restoration Hardware store in Manhattan
The Restoration Hardware Look

After we unpacked in the room, she ordered a $70 room service breakfast which was basically granola, eggs and a pot of coffee.

I was beginning to come to the realization that I might have gotten myself into a situation that was more than I bargained for financially, but it was too late.

Every night for dinner she wanted champagne and caviar followed by the most tasty victuals one could obtain in New York City, which is not an inexpensive place. I was going to have to work an extra ten years just to pay for this chick's whims.

To Symphony's credit as a C-list adult film star, she did have access to some of the most sensual events in the City.

One night she attended a private underground S&M club in Brooklyn, where the usual go-go dancers in a cage were replaced by women in bondage being whipped by masked men dressed like the Gimp in Pulp Fiction.

Another day she had a famous professional photographer do a nude photo shoot in the shower of our hotel suite.


Was Symphony enjoying her trip?


Was I enjoying my trip?


Frustrated with the skyrocketing budget required to fund her lavish lifestyle, I was at my wits’ end. I finally broke down and told her on the penultimate day of our departure that I needed some time alone.

When she left for the day, I spent most of the day staring out the window into the park and its surrounding Manhattan city streets.

a view from a fourth-story window into Gramercy Park in New York City
View of Gramercy Park from the Hotel Room

I wondered how I ended up in this situation.

Yes, I am a generous person.

Yes, I was looking for adventure.

But surely there has to be a better way than this.

The next morning, we flew back home without saying too much to each other, even though we sat in the same row.

When we landed back in Austin, we said goodbye, and I never saw her again.

The next day I deleted the Seeking Arrangement app.



My story is hardly a shocking tale compared to others I have heard.

Sure, I got in way over my head and ended up with a dent in my wallet.

It could have been far worse, however.

I have heard many women’s horrific anecdotes about Seeking Arrangement, mostly involving being catfished. 

One young woman told me that she was able to perform a reverse Google search on a photo a man had sent her, and saw that it was a fake photo from the web. 

The guy insisted he was a wealthy surgeon and wanted a clandestine rendezvous at a hotel. When she caught him in his lie and declined, the so-called doctor blocked her as a result.    

A few stories involved danger.

One woman said she ended up in a guy's S&M "murder room," and thankfully she got the hell out of there in the nick of time before the whips, chains and handcuffs were brought into action - which was the inspiration for my original horror story titled "Dating Apps Can Be Deadly."

Another Seeking Arrangement female veteran told me a story about a man who bought her a flight to accompany him on vacation.

During the trip, they had a good time, but when she went to check in for her return flight back home, he had canceled that leg.

He was trying to abduct her and keep her stranded on holiday with him so she couldn't leave!

She ended up using all the money he gave her on the trip to buy her own flight home.

Men can also get themselves into tricky situations, especially if they are doing things they really shouldn't be cheating on their partners.

One guy I know was engaged to be married, but he was also on the Seeking Arrangement site.

He ended up having an affair with a woman he had met on the app, including up to the point of his wedding day. The mistress had no idea he was engaged.

While on his honeymoon, he posted a picture on Instagram of him and his new bride at their beachfront resort. Up until then, his profile had never featured his new wife.

When he tried to break off the affair, the woman from Seeking Arrangement found his Insta account and then messaged his wife screenshots of all their salacious text conversations from the app.

NOT A GOOD SITUATION to say the least - my buddy is still in sex addict therapy at his wife's behest (yes, she stayed with him).

I hope you enjoyed this original story.  If you want to read more, check out the Original Stories and Songs section of my website.  

88 views0 comments


bottom of page