IT HAPPENED TO ME: I Almost Married a Millionaire 35 Years My Senior

The next morning when I left, there was an envelope waiting for me on the kitchen table. Inside was $1,000.
Publish date:
July 10, 2013
It Happened To Me, marriage, sugar daddies, engagements, dating rich dudes, M

I was 22 when I met Ted (names have been changed not to protect the innocent, but to protect me from any potential lawsuits).

Fresh off a successive string of failed relationships, the last of which had left me both emotionally and financially drained, I had fled my hometown in the far-flung ‘burbs of North Texas and was occupying the west wing of my recently remarried mother’s new house in the city. I lost 160 pounds of dead weight by dropping the boyfriend, and 20 more shortly thereafter. I enrolled in culinary courses at a local community college to pursue my dream of becoming a pastry chef and got a somewhat demeaning part-time job at a trendy cupcake boutique. In my downtime, I partied my ass off, made new friends, had a few one-night stands, and occasionally showed up to work still hallucinating from the previous night’s substance abuse. I was reveling in my newfound freedom, and life was good.

One day I decided, semi-jokingly, to sign up for a sugar daddy dating website I’d read an article about in Mother Jones magazine. Hey, if some old rich dude wanted to buy me dinner and shower me with gifts, who was I to deny them the privilege? My credit cards were maxed thanks to my irresponsible ex who often spent our rent money on booze, and I was making nine bucks an hour at my job. The prospect of earning some extra income just for being my adorable and charming self didn’t sound too shabby at all.

After receiving dozens of private messages from guys who seemed like total creeps (or total tightwads), Ted’s message was refreshingly normal. He said he knew he was out of my preferred age range -- according to my profile, I was looking for someone between 25 and 45 -- but he liked what he saw and asked if I’d be interested in meeting for dinner sometime. He offered up a link to his business profile on so I could clearly see he wasn’t an axe murderer (his words, not mine). Forbes? Holy shit, I thought to myself. This guy must be legit.

We met for dinner at a very fancy restaurant where each place setting had no less than three forks. I wore a black dress that I thought made me look older (but in retrospect probably made me look like a 17-year-old restaurant hostess). Ted had snow white hair but was very fit, with a warm smile that revealed teeth the color of shiny new piano keys, and a relaxed, confident air that drew me in.

He was long divorced with two kids, a son about my age and a daughter slightly older, and was looking for someone without a lot of emotional baggage who wanted to enjoy “the finer things in life.” The CEO of a technology company, he was looking to spend more time vacationing and flying his airplane and less time in the office. He commented on my “good breeding” and impeccable manners, relaying stories of a previous date with a woman he’d met on the site who had downed five dirty martinis by the time their entrees arrived.

We parted ways after dinner and minutes later my phone buzzed; it was an email from Ted. “Can’t stop smiling. When can I see you again?”

After our next dinner date, we went back to his place and I spent the night. Sleeping with a guy old enough to be my dad had seemed like a rather terrifying prospect, but it actually wasn’t half bad -- all those decades of experience bedding women obviously taught Ted what buttons to push. (We did it with the lights off, thank god.) The next morning when I left, there was an envelope waiting for me on the kitchen table. Inside was $1,000.

I was on cloud nine -- it was more expendable income than I’d ever had in my life, and besides that, I actually liked the guy. He was intriguing, incredibly intelligent, respectful, and genuinely interested in what I had to say, which was more than I could say for many guys my own age.

Within a month, Ted had convinced me to quit my menial job so I could travel with him. School was almost out for the semester, and my classmates never failed to notice when I showed up wearing pricey new boots or carrying an expensive bag.

“Ten bucks says you’ll have your own apartment by January,” a friend bet me.

Sure enough, right before Christmas Ted took me apartment hunting -- I picked out a gorgeous loft with floor-to-ceiling windows in a trendy area of town and filled it with plush furniture from Crate & Barrel, a massive television, custom-framed art I’d picked up on a trip we took to San Francisco, and various other extravagances.

Ted even put me on the payroll at his smaller side company where he brokered airplane deals; I was making $45,000 a year to be his arm candy, and that was just for rent and bills. He still picked up the tab when we went out and bought me every pair of shoes my greedy little heart desired.

He also bought me a brand new, shiny blue Mini Cooper to replace my old beat-up Dodge Neon. The vast age difference seemed hardly noticeable when it was just the two of us (he swore I had the maturity of a 40 year old, which I suppose helped him sleep at night), but occasionally, awkward situations would arise -- like when the car salesman mentioned how nice it was for him to be buying his daughter a new car. Ted just laughed and grabbed my hand, saying, “She’s not my daughter,” while the salesman turned beet red. (He still got the commission.)

I soon came to find out being a kept woman wasn’t necessarily all it was cracked up to be, though. A couple months into our relationship, we took a trip to one of his beach houses in Florida. I was coming down with some sort of nasty sinus infection, and one morning when I awoke my throat was so sore I could hardly speak. I dragged myself out of bed in hopes of finding some relief in the medicine cabinet.

Ted came into the bathroom and caressed my shoulders in an obvious bid to get my pants off.

“Aren’t you coming back to bed?”

I shook my head no, miserable and in pain, but that apparently wasn’t the answer he was looking for.

“You’re so ungrateful!” he shouted angrily, grabbing me roughly by the arm. “I do everything for you and I don’t get so much as a thank you!” (This was of course, completely untrue -- I rarely asked for anything, and always expressed my gratitude for what he did for me.) I burst into tears, telling him I wanted to go home. Within the hour I was at the airport alone, waiting for my flight home while I drowned my sorrows in celebrity gossip mags and Cinnabon.

Ted called me the next day apologizing profusely, and asking me to please have dinner with him when he got back in town. He looked me in the eyes and said he was sorry, he’d never meant to hurt me, and couldn’t I see how much he cared for me?

We continued our relationship, but Ted was tired of the city; he wanted to spend more time at his beach houses, one in Florida and the other an expensive California beach town that was a refuge for rich old hippies. For the next couple months, we jetted from coast to coast, filling our days with hiking, walks on the beach, perusing art galleries and eating at the best restaurants we could find. I left no quaint little boutique untouched, filling my suitcase with spoils in the form of designer clothes and shoes.

One day we wandered into a jewelry store filled with the most drop-dead gorgeous vintage and estate pieces, and Ted told me to pick something out. I chose a beautiful oval-cut diamond ring edged in tiny sapphires from the 1920s; he put it on my finger and asked me to marry him right there in the store. We’d discussed it before and I wasn’t entirely sold on the idea, but how could I say no? I peeked at the invoice, which he’d paid with his Amex. Twenty thousand fucking dollars now lived on my ring finger.

After the engagement, things started to get weird. I was bored of traveling and wanted to go home and see my family and friends, but Ted resisted, and when we did finally head back to Dallas he would hardly let me out of his sight. He got pissed when I wanted to hang out with my sister or girlfriends without him, saying I was obviously ashamed of him. I grew restless and unhappy and started drinking heavily -- a bottle or 2 of champagne a night helped the proverbial medicine go down easier, but I’d often wake up with a pounding headache and my shoes still on.

Ted’s possessiveness grew worse and worse. One night we argued before I headed out to see a show with some friends, and he repeatedly called my cell phone to yell at me on the drive there. I was fuming by the time I arrived and just wanted to have a few drinks and blow off some steam.

I was standing near the stage swaying to the music when a red-faced Ted suddenly appeared in front of me. He grabbed me by the arm and pulled me outside with him, telling me we were going home. I was drunk and angry and screamed at him to fuck off and leave me alone, that I didn’t love him and that we were over. He looked like he wanted to cry, and angrily threatened that everything I had would be gone -- the car, the apartment, the clothes, the paycheck. I didn’t give a shit. I turned on my heel and disappeared into the crowd.

My mother told me I was making the biggest mistake of my life by leaving him. That really hurt, especially when I found out that Ted had taken her out to a fancy lunch behind my back and inexplicably wrote her a check for 10 grand. Was that my dowry? Ten thousand dollars to sell me off to a rich man? She tried to explain that she just wanted me to be taken care of, but I was furious. We didn’t speak for six months.

I gave Ted back the ring, the car, and the apartment and everything in it, taking only my clothes and personal possessions. He tried to reconcile with me multiple times but I wouldn’t take his calls; I moved in with my sister, went back to school and quickly found a job at a restaurant doing pastry. Driving a piece of shit Dodge Neon never felt so good -- it may have been old and beat up but it was mine, and no one could take that away from me. (And hey, I still had a pretty killer shoe collection.)