Sex and the Sixty-Something Guy: Online Post to Bed Post

By Mr. X

In Sex and the Sixty-Something Guy, pseudonymous author Mr. X takes readers on an edgy and candid ride through the Wild West of Manhattan's midlife dating scene. Fresh from a divorce after decades of marriage, high-flying New York businessman Mr. X offers a raw male take on modern romance - a Sex and the City for

• Language: English
• Publisher: MrX
• Release date: Aug 29, 2023
• ISBN: 9798989029303

Book preview

INTRODUCTION

Ihope this book will be useful to you if you’re about to date again in mid-life. If you’re a man, it will help you navigate the pros and cons of dating in the app and matching era, along with highlighting the literal pros and cons within the matchmaking industry. If you’re a woman wondering why you didn’t get a second date when the first one seemed absolutely fine to you, this book many also be helpful. If you’re married and wondering if the grass is greener on the single-and-dating side of the fence, then read on.

As a fifty-something man who settled down early and was divorced after nearly four decades of marriage, I had absolutely no idea what to expect when plunging back into the dating pool and was hoping for a perfectly executed swan dive. So to ensure that everything would go as smoothly as possible, I decided to get an apartment in Manhattan, even though I had a house in the suburbs and a summer house on a lake. Although I had spent decades working in the heart of New York City, I always lived in the suburbs with my wife and children and commuted in. I knew city life would be quite a change from living in the suburbs, but my children were grown and I was set financially, so I decided to give it a try as part of a new life adventure.

My background: I was married in my early twenties and we quickly began having children, so I never experienced those freewheeling years of sowing my wild oats and dating around in my twenties. I had a family to support and a career to build, so I became an adult early in life. I divorced in my mid-thirties and soon remarried, and my second marriage lasted for more than twenty years. I have a wealth of children and grandchildren now, and we’re a close-knit family.

I’m proud to say that I’m a self-made man who built a successful career and am an enterprising business owner. I’m proud of the things I’ve achieved, the places I’m able to visit and experience, and what I own: a beautiful house in suburbs, a summer home, a city place, expensive cars, etc. I say this because when dating, you have to be able to discern who is excited about you for who you are as a person and what you’ve achieved versus those who are excited primarily by what you own and can provide for them. In other words, knowing how to pan for the gold diggers, then tossing them out.

It didn’t take long for me to realize that to meet the right person, I would need to show my dates the real me. That is to say, the guy in the nice suit is not entirely me… at heart I’m a jeans-and-T-shirt guy who happens to have to wear a suit to work to appease my clients. My clients are all from corporate America, so I’ve learned to adapt to that culture over the years and am multi-faceted. After work, I would often run back to my apartment right before a date to change into something a little less stuffy.

I met several… OK, dozens of NYC women, and the majority of them were very well dressed and mannered, had traveled extensively, knew of the finest restaurants, and had seen the best and most recent shows on Broadway. But after I peeled back the layers, I discovered they had a small, rented apartment, no car, and owned nothing but clothing. I thought it was peculiar that they reached the age of 55 to 60 and still had nothing to show for an entire lifetime of working. But I realized that some of them ended up with the short stick in a divorce and had married for love, or gave up careers to raise children, or had pursued creative endeavors they loved that didn’t pay well enough — such as small business owners, chefs, dancers, teachers, photographers, artists, directors, coders, public defenders, social workers, journalists, copywriters, designers, etc. — or they hadn’t found the right career after a lifetime of searching, or depended on others to support themselves, or cared about other things more than creating wealth. There were a variety of reasons, but it still seemed surprising to me.

The women who were legitimately successful and wealthy had few qualms about letting you know it. They were proud of what they had achieved too. And some were also wary of gold-diggers, unwilling to support a man who couldn’t carry his weight.

I’m a gentleman and was shocked by how many women wouldn’t let me get them a taxi, because they take subways, or wouldn’t let me get them an Uber, perhaps because they didn’t want to disclose their address.

In general, the NYC gender breakdown is 53% female and 47% male, and 57% of the women in the city are single. I also dated outside of NYC in its tri-state area and beyond, and used various matchmakers.

When I went on dates, it was pre-determined that I would pay to avoid the awkwardness of hashing it out later. At some point after going on dates and meeting in noisy or cramped restaurants where there was no privacy and you were practically sitting shoulder-to-shoulder with strangers at the next table, I started choosing the restaurants where I would meet my dates. My choices were places that had intimate tables for two and were on the quiet side so you could speak in a normal tone.

Online Dating Apps and Matchmakers

I gleaned a lot about the various dating apps (eHarmony, Silver Singles, Elite Singles, Match, Our Time), as well as the three matchmaking services I tried.

I started with online dating apps and switched from one to another when I didn't see any new people after a while. I used eHarmony, Match.com, SilverSingles and maybe one other. Then I heard about Talkify, which is a matchmaker service where a person is assigned to you to get to know you. You meet with a person for coffee or lunch and then for approximately $1500 you will arrange 5 or 6 dates with different people. No names or pictures are exchanged, which is refreshing — you are simply told which restaurant to meet at and what time and the reservation is made under your date and your first names (i.e. Matt/Melissa). You also tell your coach what you are wearing. It was fun and I must admit I was never disappointed with the dates I had. One of the rules at Talkify is that you don't discuss what you paid for the service. I found out later that this is because some people are paying clients and others are just dates. It is assumed that the guy pays for dinner. It was actually kind of exciting going on 'blind' dates.

The Apps

I’ll start with the online dating apps. What an eye-opening experience this was. Most people post pictures that are not recent, and in some cases, even Photoshopped. I was amazed what ‘FaceApp’ filters can do after I met some dates in person. Did a date assume I wouldn’t notice that she looked significantly different than her photo? Filters can shave off a decade or more. I was actually more amazed that people would lie about their age. After all, when looking at my profile, they could see from my white hair that I’m not lying about my age. What’s worse is if you do lie, at what point do you come clean? Do you slip up after a few drinks? Does it happen after many dates when you’re at the airport and I glance at your passport? Do you really want to start a new relationship with a lie? For example, I was out with a 55-year-old woman who, after her second drink, said she retired early and started collecting social security, which you cannot do until you’re 62. To quote Mark Twain: If you tell the truth, you don't have to remember anything.

As you swipe through the endless stream of profile pictures, and you finally find one you like and they respond positively to your inquiry, you grow genuinely excited. You hope this is the one as you prepare for the date. And more than a couple of times, I was disappointed, annoyed, and even depressed by how the date turned out due to these deceptive profiles. Anticipation builds all the way up until date night… and then trust me, so many times you get disappointed. I’m a gentleman so when the woman who arrived to meet me was so clearly not the woman in the picture I had liked, I would still sit through dinner and then return home a little pissed-off. I met one woman whose face had so much Botox injected into it that she appeared to be wearing a hard plastic mask. I was mortified to be seen with her. How can this be a beauty standard? Another time I sat waiting in a small restaurant when in walked not my imagined date — the woman featured in her profile picture — but a considerably older and heavier version of her. It felt like a bait-and-switch tactic. I sat through dinner but was inwardly so disappointed.

I was once so upset by someone who posted a picture from 10 years and 20 pounds ago that when she texted me about what a lovely time she had with me on our first date, I couldn’t help but respond, I wish I could say the same, but I feel you misled me with the picture you posted. Her response was to say that the picture was only a year old, which was clearly another lie! I was tempted to quip, Honey you had one really bad year, but I didn’t.

You will experience all of these types of disappointments and likely even more, but every now and then you will meet someone who makes it all feel worthwhile.

The Matchmakers

The matchmaker experience is better, but there is a more limited number of people who can pay for it, so the dating pool is smaller. Matchmakers charge anywhere from $5,000 to $100,000 for a specific number of curated dates. I interviewed a few of them and quickly realized that many will tell