The Outrageous Break-Up Quiz and Other Grim Tales of Dating Finance ProsS

After writing about the crazy J.P. Morgan analyst who stalked his ex across the Atlantic pretending to be an Israei spy, and reproducing the insane 1,600-word letter from an investment analyst demanding that a woman he went on a single date with apologize for leading him on, we figured we'd open it up to our readers for more stories from the front lines of romance in the financial industry. And boy, did you all deliver.

Both men and women wrote in to tell us their woeful tales of dating brokers, bankers, analysts and managers. And they were pretty bad! One woman said she had a "horrible" story she was afraid of sharing because her ex-boyfriend—"a very high profile guy"—might sue her. "That's the kind of thing he would love to do, sue his ex-girlfriend," she told us. Which says about as much as the story itself.

The Quizmaster

I had dated this guy for a little over a year, works for one of the Big 4 - here are some excerpts from one of our many break-up exchanges. I'll let the email speak for itself, took out the more personal stuff. But yeah, this was pretty typical.

OK what I want to talk about is this, all of the following points must be resolved. This may take time by sheer logistics alone but because you have difficulty saying things why don't you answer the questions in writing first. You have to provide the written answers to me if you do so, I will not need to see them ahead of time but I reserve the right to read all of them. The longer you make your answers the better this will be, spend as much time as you need, if you can't get it done by tonight or it will take you a few days that's fine. Sometimes Yes/No answers are OK but make this thing as perfect as one of your college papers.

DO NOT PUT THIS OFF. If you wait you will hurt your chances of us being together. I'll give you a dead-line: Thurs evening, I know you work hard and are busy. I would hate if you take as long as Thursday evening

...

Why you were unhappy with us:
Are there things you do not like about me?
Are there things you do not like about us?
Are there things you don't like about yourself when it comes to us?

Name as many things as you can you would change about. Again, you must list everything that bothers you.
1. me
suggestions: I interrupt you, I need to enunciate when I speak
2. us
3. yourself

...

Where do you want to be in?
6 months
1 year
5 years
10 years
20 years
50 years / retirement age

...

In Exercise A, you must cover any topics you bring up for previous periods

Exercise A
- List the reasons you were unhappy November 2007 - present
suggestions: Financial reasons, Emotional reasons, Our relationship related stuff, professional stuff
- List any things that made you happy November 2007 - present

List the reasons you are unhappy now:

List the reasons you are happy now:
__________________________

For the Exercise B it might make sense to break it into three tiers(OST):
An example for me:
Objective I want to be in better shape
- why should I bother? I want to have better health, I want to have better sex, I want to be more sexually attractive to women, I want to look and feel better about myself, I will be better at everything else if my health is in order, I will meet people by doing outdoorsy stuff
Strategies: I want to improve my 1. cardiovascular capabilities 2. flexibility 3. muscles 4. I want to do outdoorsy stuff this summer
Tactics/Action Items:
1. a. ride a bike for fun & to work
b. go on hikes
c. do yoga everyday, do a yoga class once a week
d. join a gym?????
2. a. do yoga everyday, do a yoga class once a week
3. a. join a gym??????
b. do yoga everyday, do a yoga class once a week
4. a. Do outdoorsy stuff with friends
b. ride a bike
c. go to the beach
d. fear getting sunburned less
e. book vacations and 3-day weekends

Exersice B
List all of the specific things you will do to improve:
1. Your physical health
2. Your emotional health

The 'Weird, Comical, Slightly Psychotic' Guy

The Outrageous Break-Up Quiz and Other Grim Tales of Dating Finance Pros

I've not dated this 'gentleman' but I did meet him at a bar last friday when I was out with another friend of mine (a guy). John (the financial industry professional - he claimed to 'manage money') was standing at the bar by himself and made room for me and my friend to step up and order. We got to chatting and he was plainly a weird guy, but weird in a comical, slightly psychotic way. One of his stories was about going to Brazil and how prostitution was rife and he would never pay for sex. Then after some questioning he admitted that he had gone to a party where the host encouraged him to have sex with the prostitutes who were there but he wouldn't. Again, after some light questioning for details it didn't take him long to admit he had paid every prostitute there to have sex with thim.

By the end of the night he asked my friend and I for our numbers, and unfortunately I was too drunk to think of a fake number in time to save myself. After a couple of messages I didn't reply to I gave him the nicest possible 'Thanks but no thanks' text and this is what follows (screen shots for veracity below):

'Hi Alex. Well thanks for at least replying to me. I wasn't expecting to date u as there is an age gap. (& u r a lot prettier than me lol!) Just some fun - that's all I was thinking (hoping). I did enjoy the drink and the eye contact with you was special. Please keep my number and if u ever fancy a random night out with a nice guy who'll treat u like a princess let me know!! I also have a naughty adventurous side in that I occasionally go to a swingers club of which I am a member & also other organised parties for likeminded singles/couples. If this intrigues u let me know too!!!! :))x'

The magic of the message that I will also treasure is the transition from 'I'll treat you like a princess' to 'I want to fuck you...possibly in a group setting'. Flawless.

The Jack Rabbit

I've been a restaurant manager my whole career, in places frequented by financial professionals, and can absolutely testify that as a group they're douchebags. Entitled, overgrown frat boys with eggshell fragile egos. Narcissists who are deaf and blind to anyone or anything but their own desires. Impossible to communicate with on any meaningful level - the only thing they understand is money and perceived status. On the plus side, restaurants are vanity investments, so at least they're good for that.

It was with a great deal of trepidation that I broke my own rule and accepted a date with a banker. He was a youthful 40, great on paper, seemingly normal. His friends appeared to be normal as well.

The red flag I missed the night we met and he asked for my number was that he sat for hours with his buddies after his check was paid drinking water, openly admiring me, while other very impatient people waited for them to get up. He would psyche us all out every time he got up to use the restroom, which is the universal sign a table is leaving, only to return and resume his hydration. He must have been the alpha in the group, since his friends were at that point wasted and done drinking but remained. I had to ask them to leave.

But he was good looking and sweet and kind of funny, not creepy at all, and I guess my ego needed it? Anyway.

We went out on our date to an uber-exclusive restaurant that was trying to recruit me. I was supposed to be going incognito, to suss out the place without the staff knowing I might be their new leader.

He was late for our reservation. And brought two friends. Incredibly embarrassed, I spoke to the maitre d', fully recognizing that what I was asking for - on top of being late - was absurd, but wrangled a table for four. Later on when I got the job, she told me my reservation was made the day of in a prime time slot indicating I knew someone up high, so they turned the book upside down to accommodate our party, and quickly. So much for keeping a low profile.

He ordered his meat well done. And drank water, turning his nose up at my scotch and wine.

Let me cut to the chase. The kiss at the end of the night. Imagine someone on the other side of a window pressing their face up against the glass. Vacuum seal. Now there's a hole in the glass and their tongue is stabbing at the air, of which there was none in the actual kiss. It was the worst I've ever received in my life.

It was so bad that a couple of dates later (I know, I know) out of strictly morbid curiosity, I slept with him. I just had to see how bad it could be. Plus I had enough confidence in my own skills to make it bearable. Wow.

It was no more than TWENTY FIVE SECONDS of the hardest jack rabbit pumping of my life. There was no way around it, I had to lay still and take it. When he rolled off me and immediately went to the bathroom to remove his condom and wash his dick in the sink, I laughed in disbelief, my thighs reverberating from the pounding.

He climbed back into bed, his bikini underwear back on, and pulled all the covers off me and onto himself. Seconds later, he proceeded to snore like a bear. Upon leaving his very expensive high rise building, I imagined his doorman thought I was a prostitute based on the short time lapse since arriving and my clearly post fuck appearance. I needed to get out asap, and his bathroom, while expensively marbled and somewhat bare, was truly grody; the toilet seat had clearly never been lifted and was glazed with urine.

I dumped him over email, but he still wrote every other month for a year to ask how I was. I never responded. Then it stopped. Cut to the present. I'm running a new place in his neighborhood and sure enough, he walks in. He tells me how great I look and like I lost a lot of weight (I didn't, I'm exactly the same size) and I get him a table. He sits for hours, again with the water. Finally it's time for me to leave for the night, so I go to his table to say goodbye.

He stands up to embrace me. "We should go out," he says.

"No," I laugh. "No, we shouldn't. Ever again."

"I'll email you!" he promises.

The Joan of Arc Expert

One of the funniest things about dating serious financial industry types is that they usually are very knowledgeable about finance and not much more. I made the mistake of dating my own stock broker once. He was referred to as "The stock broker to the stars" because I guess he made a lot of rich/famous people even more wealthy. But dinners with him were so awful, I wanted to stick my fork through my eyeballs out of boredom. I would try to make conversations with him and he had nothing to say. He could only talk about money matters, how important he was and how important his other clients were. Pick a topic...ANY topic...that I would try to discuss, books, films, tv shows, current events, news, history...and he had NO idea what I was talking about so essentially I would have to talk to myself for the entire dinner. If we went out with other people it was not so agonizing, just a little embarrassing that we had less and less in common as the "dates" continued.

One conversation I still recall with laughter was about Joan of Arc. I caught his eyes glazing over and asked, "Do you know who Joan of Arc was?" "Yes," he replied, "Of course." I asked who he thought Joan of Arc was. He replied, "The man that built the arc."

You may have to think about that for a while...it took me a while to realize he was talking about Noah.

The Asparagus Fan

I am an investment professional. I like to think I leave my crazy pants at home when dating. My boyfriend of 2 years has stuck around which I'd consider a good sign. So one can work in finance and not be a deranged stalker.

That said, I've made the old 'pooh where you eat' mistake before and dated a couple of guys at work. While not crazy per se, they do demonstrate some awkward social skills. Here are some actual quotes:

  • "your body type isn't one I'm usually attracted to but I am sexually attracted to you." (I'm 5'5 and 120lbs....I didn't ask him for further clarification)
  • "I like your hair cut! It's a good thing you got it too because I was going to stop dating you if you hadn't."
  • "I love asparagus but it makes my shit stringy." (said on date number 2)

One also better be ready to hear lots about fantasy football, studying for the CFA, Chinese IPOs, going "double long", and your own last name. (never had guys I've dated call me by my last name except other investment pros).

The Objectivist

(From commenter Nohio.)

I'm new in town. One of my few friends, Angie, sets me up with her buddy the investment banker. We went to dinner. This is a brief summary of the night.

(Drink One: Wine. General conversation about how we know the mutual friend, etc.)
Me: Tell me about yourself.
Investment Banker: I graduated with sixteen degrees and now I work at this firm. It's very complicated.
Me: I happen to have a degree in business. Enlighten me.
Investment Banker: I love my job, it feels like I never left the frat house. Let me tell you about my recent bonus...

(Drink Two: Martini)
Me: What do you do in your free time?
Investment Banker: I go out a lot. I read and go to shows sometime too. You're gorgeous.
Me: Oh, nice! What's the last book you read?
Investment Banker: Atlas Shrugged. I try to read it once a year.

(Drink Three: Vodka. Lots of vodka. Where the fuck is my food?)
Investment Banker: Check this out! (Shows me the tag on his jacket.) This is a custom made suit.
Investment Banker: You're very pretty. We're really connecting here. Let's go have a drink at my place.

He continues to pressure me into going home with him for the next half hour. Every line in the book. Maybe if he didn't talk the entire night I would have been interested? But anyway, we walk out of the restaurant, he grabs me, pushes me up against the building and attempts to make out with me/give me CPR. Definitely not romance movie material.

The next day he texts me at 10am. I'm still asleep and don't respond. So he texts me again at 10:30, 11 and 12. I'm trying not to burn bridges here, I'll probably see this kid again and I wanted to talk to Angie first. I'm guessing he started drinking around 3, because that's when the texts about getting me naked and fucking me on a bed of money start filling up my inbox. I tell him I'm not interested. He's shocked and starts calling me a whore. It was like no one had ever turned him down for sex before. The next day he apologized for his behavior and began planning the second date that I never agreed to. I reiterated that I wasn't interested, but he wouldn't give up. I just stopped texting him back. Two weeks later, he tried again. It took three months for him to stop texting me altogether. I realized that Angie and her entire group of friends were terrible people shortly after this horrendous date, so hopefully I never have to see him again.

The Serial Killer Dater

I met "guy" in London. He is European and was working there, I was a PhD student. When we met, he was in the process of breaking up with his ex. While she still lived there, he said it was to give her time to get a new place and that she was "psycho". First red flag - still with someone when we met.

We dated for a year and a half, all going well, meeting each other's friends and families early on, traveling together, talking about the future, etc. He bought a house in central London and I moved in, so I wouldn't have to go back to the States (I couldn't afford to live on my own in London). Shortly after he got an offer to temporarily relocate to NYC, with the idea that he'd be back in London within a few months. I said go for it, feathering the nest for his return.

He started to get distant when he was there, hard to get a hold of, shady about where he had been, who he was hanging out with. I went to visit and his roommate HADN'T HEARD OF ME. Another big red flag. He said they weren't close.

One of his parents passed away and I was there for him and his family, despite the growing distance in our relationship. I knew something was wrong and several months later asked him if he had slept with anyone else, saying we could talk rationally and not yell. He got mad and accused me of cheating (RED FLAG) and said the passing of his parent was weighing on him.

That night, unconvinced, I did something I'm not proud of, I checked his blackberry and found that he had been seeing 4 women for nearly a year. There were sexy messages sent the week of his parent's wake. He used pictures of my nieces, saying they were a friend's kids, to get girls to shop for cute stuff for them. There were many casual sexual messages indicating that these were ongoing relationships.

I wrote down the names and numbers of all the women before confronting him, in case he tried to delete them.

Here's how to handle this ladies: In the morning, I made him call each of the women in front of me, apologizing to them for lying, saying that he was in a serious relationship and that he was seeing multiple women. I also spoke to them, as a sisterly courtesy. It wasn't their fault, I'm sure they're all lovely, but they deserved to be warned and he deserved the punishment of facing the music. It was awesome, he cried and apologized and even talked about how now he knew I was the woman he wanted to marry. Best revenge ever. Don't yell, scream or break stuff, then you're just another "psycho." Be calm, call him out, then move on.

The Master of Metaphor

I was told by a gay finance HR person that I "performed well during the onboarding process" of the relationship (i.e. the first 3 months).

The Entrepreneur

Hi [REDACTED],

I would like to be completely honest and just have good times together and help each other and maybe kiss each other once in awhile. See how you feel, you will not get any uneeded pressure from me. Can you go to Florida with me for a few days? Its strange I feel very close to you even though we don't really know each other. I'm just watching the news channels at the moment. The DOW is down but I feel up as I am speaking to you right now. Give me an update darling. Can we get together tomorrow for a while? Also I have to see clients in Orlando Midweek and then will drive to my condo in Ft Lauderdale. It would be great if I could fly you down there for a few days so we could do some things together. Let me know about tomorrow and how you feel about these upcoming things.

Talk to you soon.

All the best

[REDACTED]

Hi [REDACTED],

Well i'm very cuddly and nice under the sheets and really warm. You want to try and see how you feel? Also last week Krystal sent me an e-mail thanking me for dinner and asked for my number. I told her I was glad she had a good time as I was fine with her coming because I was very fond of you and if she wanted to come it was okay. Do you want to have a threesome with Krystal Friday night in NYC Hotel? It should be relaxed with a lot of sensuous passion between all of us. Would you both like that and feel good about it? I really would like to kiss you passionately on your own one day. I have no germs. Do you?

Warmest Regards,

[REDACTED]

...and finally, a defense of financial industry professionals

I feel like there should be a support group for people who've dated financial people. They are by nature incredibly intense and alpha, and coupled with (let's face it) the nonchalant way they can throw money at things, it can start off as very attractive and then sour pretty quickly. Social skills are usually underdeveloped. I was with a finance guy for two years who, from what I could tell, was one of the good ones. Very thoughtful and sweet and loving, but absolutely the most insane person I've ever met. I can't tell you how many fights I broke up, bars we got thrown out of, or lines we did. Instead of a partnership, it really turned into me being part mother, part brother, part social worker, and we both resented it.

The guy in your totally inappropriate email is under incredible pressure, more so now than ever. They seem to have real trouble making genuine connections with people for all kinds of reasons: the 16-hour workdays, being surrounded by douchebags all the time, general smart-people awkwardness, insane families (in my case). I'm not excusing the email, but I am saying there is a real person behind it, and he is applying the same intensity and analytical mind to dating as he would to his work.

He is completely out of touch, but most of them are. Definitely the apology is ridiculous. All the same, he doesn't come off as stalker-y, he used good grammar, he clearly just wants an answer. I say send an email that can't be misinterpreted: "Thank you for the date, but I am not interested in you. Please do not contact me further." He may write back another too-long email but then be done with it.

[image, of two people who are not financial services professionals and are, we imagine, rather nice, via Shutterstock]