It Happened To Me Contest Entry: I Lost 98 Pounds And Fell In Love By Dating Escorts

Diet, Exercise and Gigolos -- 
8 different companions, 20 dates in 13 months
 98 pounds/42.5 inches/12 dress sizes lost.

Mar 5, 2013 at 5:00pm | Leave a comment

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By Heather Smith (@MorroBayHeather)

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At 5’1” and nearing 300 pounds it’s safe to assume I was disconnected from my body. (Not everyone at that size is just so we’re clear).

My state of being was the result of years of unhealthy comfort eating, workaholism, sedentary lifestyle choices, and a deep-rooted depression tied to a 2008 mid-term pregnancy loss (self-inseminated at home with anonymous donor sperm).

I dropped about 20 pounds in 6 months but still my doctor gave me the well-deserved yet graciously delivered lecture on my increased risk of heart disease, diabetes and cancer due to high cholesterol, overall health numbers and family history.

 I’d researched professional companionship a few months before that doctor visit and had half-jokingly promised myself a date for my 39th birthday with the caveat that I had to get below 250 pounds.

There was no set plan; I simply cut out carbonated drinks, pasta and white bread. Nonetheless a couple weeks before the deadline, I hit 248 and worked up the courage to call the booking agent, aka The Voice.

Unsure of how this worked, I gave him as little personal information as possible while still allowing him to confirm I was who I said I was. I told him who I was interested in seeing in LA. Unfortunately the guy in question, the one I’d visualized through the dark months of soda-withdrawal, wasn’t available the weekend I’d be in LA but The Voice assured me all the men he represented were respectful so we talked a bit about personalities and scheduling.

I decided on an equally attractive substitution. He was actually more of my physical “type” but I didn’t remember seeing him on the site when I originally found it. 

So I booked my first professional. An escort. Caliber companionship of a vetted nature.

Call it whatever you want except I will not use the other “p” word as I have never paid for sex. Just like any other date, sometimes sex happened and sometimes it didn’t -- sex was not guaranteed and not part of the financial arrangement.



It’d be an understatement to characterize my mental condition as wrecked in the hour leading up to meeting The First. I showered, went through the requisite beautification rituals, downed a glass of Syrah, and smoked a joint (prescription!) but despite those efforts was a pacing, mind-racing, bundle of nerves. The voice in my head was shrill, panicked and overwhelmingly incredulous.



When the knock sounded, I nearly chickened out. Some external force pushed my hand toward the door handle and there he stood: well over 6”, fit and lean, dark hair, wearing an impeccable light blue dress shirt, navy slacks and brown Italian shoes. I’d worn a size 26 maternity sundress which showed off my huge boobs yet graciously camouflaged most of my flesh rolls with the help of a strategic shrug.

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The size 26 maternity sundress for my first professional date in August 2011





I’d planned a private multi-course dinner on the executive level of the hotel. I figured if I was paying someone to go on a date with me, I’d make it one helluva date right? Go for the full blown romantic cliché that Hollywood has convinced us is “normal.”


We spent a majority of our time together talking -- getting familiar, standard background questions you’d discuss on any first date: what we did, hobbies, places we’ve visited or lived. The conversation flowed easily, he was engaging and charming, and instinctively knew when to listen versus when to talk.



Having resisted the dark chocolate mousse (regrettable), following our fruit/cheese plate (boring) we retired to the suite’s living room with more wine and bubbly water, settling in on the light blue plush sofa. Truly alone at last we could discuss some of the more intimate questions, such as what made me decide to book a professional in the first place. 



At one point he moved in to kiss me. I instinctively recoiled, broke into a cold sweat and stammered an apology/explanation but all of the words came out jumbled. It didn’t matter. He was a professional. Reading a woman’s signals is his job. He adjusted his spatial relationship to me by dropping to his knees on the floor.

He unbuttoned the top of his shirt, placed my hand on his chest so that I could feel his heartbeat and positioned his face a few inches in front of mine. Eyes locked, he instructed me to take deep breaths, in and out, synchronizing our bodies and slowing my pulse until I was centered. Then he made us alternate our breaths so that we were “taking in one another’s essence.”

His breath was sweet from the wine and it proved an effective technique to turning my frenetic chaos to calming peace to... something else. Something that makes your core tingle with anticipation and makes skipping dark chocolate mousse seem insignificant. I didn’t recoil when the next kiss came.



Afterward, I knew I’d stumbled into an experience I wanted to have again and being true to my Virgo nature I formalized a complete weight loss plan with hard & set goals, the tentative schedule of dates as a monthly reward for hitting those goals, and looser date proposals for significant milestones.

I made an overarching commitment of dating only the men The Voice represented for one year. I intended to culminate the project in a fabulous 40th birthday party in August 2012 and I wanted the ultimate date for it, provided I earned it (I did).


I discovered what I loved more than food, what could keep me mentally focused and reinforce healthy decision-making: planning the next date, the visualization of who I’d see, where we’d go/do, what I’d wear. I embraced all the couple’ish things I’d never done before given my career-focused habitual singleness: couples massages, concerts, strolls through art galleries. I tried different guys and different cities.

I lucked out and a majority of the professional men I dated, I clicked with but even in the few exceptions where there was no chemistry or common ground at least I didn’t dine alone in a fancy restaurant. 

So that’s what I did:
 Diet, Exercise and Gigolos -- 
8 different companions, 20 dates in 13 months
 98 pounds/42.5 inches/12 dress sizes lost.

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A year later at size 14 in the same sundress


No weight loss surgery. No diet aids/pills/treatments. No growth hormones.

 Instead I did exactly what they tell you: made smart food choices, ingested fewer calories than I burned, regular fast-paced cardio, and light strength training. Mostly it comes down to one thing: WILLPOWER. 

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No big surprise, the right motivation (fun times with hot guys!) when applied was successful. I confided in them my fear of the gym; they provided solutions to easing me into it until I overcame all anxiety tied to formally working out. They influenced my diet and provided sound guidance on how to get more nutrients with fewer calories.



What my plan hadn’t accounted for were all of the psychological and emotional benefits of dating professionals. The guys started playing various roles and fulfilling specific needs I didn’t realize I’d been ignoring: The Motivator, The Healer, The Fighter, The Glue, The Giant.

I started the formal plan in September 2011 and by April I had fallen completely in love with... myself. They helped me work through my body image issues in a way that no therapist ever could. They helped me find my inner strength and confidence. By rediscovering my sexual self and the power that comes with it, I became an improved woman in all areas of my life.

Going into this, I had no idea how fucked up I was in regards to men/women relations, sex, or what true intimacy was. They taught me so much about myself and relationships that I’m writing a book about it.



The mental, the physical, the emotional -- it’s all connected and requires balance. I hate that we live in a culture that de-emphasizes, nay, disapproves of the potential benefits of sex outside of a heavy, committed monogamous relationship.



I’m still a “fat” girl, a respectable size 12-14 depending on the label and cut but I don’t feel nor behave like a fat girl any longer. I’ve arrived at body acceptance. I’m dating “civilians” again, confidently. 



At my check-up last October, my doctor was elated. All of my stats were positive: my good cholesterol was elevated while the bad was low, glucose levels were normal (no more pre-diabetes!), blood pressure spot on perfect. She didn’t care that I’m 25 pounds from my goal weight; she focused on the success and stressed the importance of maintenance. She asked the right psychological questions regarding my sex life (she doesn’t know the details of the professional dating plan but she must have suspected something from my sudden insistence on more frequent STD testing).

Satisfied with my answers both physical and psychological, she ended our appointment with the simplest of statements, “Heather, you’re healthy again.”  

Indeed, I am. I thank all of the professionals who helped me along my journey.