Dating/Dating Advice

Playboys & Predators; The Perils & Pitfalls of Online Dating Over 50

I believe in love despite all empirical evidence to the contrary.

If you’re single and over 50, it’s likely you’ve experienced some level of relationship trauma. You have baggage that you inherited, created, or fallen victim to. In my case, all three of these are true.

When I found myself single again after a 13-year relationship at the age of 54 and all my friends encouraged me to try online dating, I packed up my metaphorical baggage to dip my toe into the online dating pool. That was 2018. I am now almost 59 and still single.

After years of online dating and my recent encounter with a grifter of such prominence that he has his own Wikipedia page- I understand now that online dating comes with dangers I am no longer willing to risk.

The optimistic 54-year-old healing from that devastating breakup in 2018 has given way to a jaded and suspicious single woman when I think of finding love on a computer or phone. Now, this is not to say that I do not believe in love. I absolutely do believe in love — I believe in love despite all empirical evidence to the contrary. I am just not convinced the kind of love that I’m looking for will be found online. But in the name of helping other women, the perils lurking in the cyber world for single women today merit examination.

I had very little online dating experience when I entered the dating scene in 2018. After two long-term relationships- one marriage of 12 years and one live-in partnership of 13 years- I had no idea what to expect. At this point, I had spent 25 years of my 54 years with the wrong person. I knew both relationships were wrong and stayed in both for too long.

So, as a newly single woman, I hoped to find that real love connection. I know it sounds cliché, but I wanted to find a true partner in my life — a true love relationship that was mutually respectful and supportive.

In my fifty-four years of experience, while I knew I deserved this, I had yet to find it in any of the men I had been with. In between the two long relationships, I had a few smaller relationships here and there, but those were all men I met organically — either through a friend or in line at the airport, meeting in the casual living of life. When I decided to go online, I had no idea what to expect. So, I did what I always did in my life; I took people at face value. I believed in the way men represented themselves. That was my first mistake.

Playboys were the first thing I found on an app. Of course, they never SAY they’re playboys. They put things in their profile like, “open to long term”, “friends first and let’s see where it goes”, and “possibly start a meaningful relationship” These are code words for I’ll get you to sleep with me and then I’ll ghost you to move onto the next woman- whom he almost certainly is lining up as he is texting with you.

Word choice gives men the out—Open, Let’s See, and Possibly. All code for if it doesn’t work, the woman will blame herself because that is what women do — we blame ourselves for not being enough.

Upon first entering the online dating world in 2018, I discovered that dating as a 50-something woman was a lot more complicated than dating had been in my thirties as a newly divorced woman. These differences went beyond the extra 10 pounds, a few gray hairs, and a size 6 frame that now required running 20 miles a week to maintain. I signed up for Match.com in earnest. Several starts and stops resulted in many bad first dates — several mediocre second dates — because, after a bad first date, I made an excuse for the bad date to give the man one more chance.

I had no third dates. Months passed, and while I found there was no shortage of men who wanted to go out with me, I found that I was not all that excited about any of them.

During this time of bad dates, I also realized that I missed physical intimacy. That is when I met Spencer (not his real name) on Bumble. Unlike my other bad dates, Spencer was handsome, charismatic, and easy to talk to. I felt a spark. He had in his profile “looking for long term”. I took him at his word. On our first date, we chatted easily. He asked thoughtful questions. Did I mention he was handsome??? We slept together on our second date; it was amazing. Of course, I had not had sex in almost two years, so probably not surprising.

Then three weeks of nothing — no answers to my texts and his phone went right to voicemail. I had been ghosted. I’m confident that if you talk to anyone who has been in the online dating world, you will hear similar stories. While that was not the outcome I had hoped for — I did get something out of it. Yes, that. But I also learned a lesson in being a bit more jaded and protecting myself a bit more. Now, I would read profiles more carefully and be much more circumspect in men who got close to me. Now, years later, I look back on that time as a learning experience with no regret.

The predators online are much more dangerous and come in so many forms, there are too many scenarios to go into here, but I will give you a couple of the most dangerous. Sometimes men misrepresent their financial status or work. Sometimes by a little; often by a lot. While this may seem harmless on a date or two, it is not someone you want to have a partnership with.

Other times, they don’t give you their real name, making a background check meaningless. Yes, I did subscribe to one of the many services online where one can do background checks. I did this before every first date, and recommend you do the same.

When “Adler” came across my Match profile in July 2023, he had a detailed profile and sent thoughtful messages. We chatted on the phone and agreed to meet for dinner. While he did show up late, he was thoughtful and charming, and he looked like his picture. Our conversation was easy; he was smart and interesting. He refused my offer to split the check. I googled him before our date and found no online presence. I ran a background check — nothing that matched up with what he told me. He had a common name — so when I googled it, SO many things came up, but none of them matched up with his story. I asked him about this at dinner. He said that his family trust had been violated by a third cousin who changed his name to the name of the trust to secure credit, so the family had the web wiped of information so no more damage could be done. Something didn’t pass the smell test, but I ignored my instincts.

I traveled out to California for my daughter’s wedding the next day and we kept in touch via text message and phone calls. Something felt off, but with the wedding, I put that feeling behind me and agreed to meet him for a walk on the Saturday after I returned.

As we were walking, I asked very specific questions to try and glean some information that I could confirm. I wanted him to be real. I wanted him to be who he said he was. But after a 4-mile walk and a two-hour lunch, nothing he said added up. But one thing he said stood out to me and I knew it could be checked — He claimed to be the cousin of Gavin Newsome. Ok, Mr. Google — Gavin Newsome relatives. His mom, Tess, had died years before. So, Adler’s reference to her in the present tense was all the confirmation I needed that he was not who he claimed to be. But who the hell was he?

And that’s when Pimeyes.com solved the mystery for me. Pimeyes is an online reverse image search engine. It turns out that “Adler” was actually a well-known grifter whose mugshot revealed to my horror. In order to protect my safety, I’m not including his full name here — but if you google PPE Covid fraud, you will find him.

While I won’t go into the 20-year criminal history here, nor will I outline the safety precautions I took to ensure my safety, I will leave you with these words of advice — If you are going to date online, do background checks, use Pimeyes to reverse image search, and most importantly, trust your gut. Be safe out there ladies.