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Sex, Lies and Online Dating Over Age 50

An honest look at the search for companionship.

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cup of coffee keyboard and computer mouse on desk in moody blue light
Tom Eversley
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I am a 58-year-old woman who has gone on 100 online dates over the past two years. A few good dates — and too many that were really bad. There are many articles and books that give single women over 50 advice about getting out there and dating. I have found this barrage of how-to-find-love-again material contradictory.  

So, let me be straight up: This is not an advice column for ways to find a mate on a dating site. I read everything about dating over the age of 50 before I hopped online. I was hoping someone would tell it like it is. They have not, so I will. Here I will take you on my comical, awful, totally honest online search for companionship.

How I Got Into It

I had been divorced for eight years, and my son was now a teenager and less dependent on me. I had moved to a new area with lots of professional men over 50. I had quite a few 50-year-old friends doing online dating and saying they were finding a love match. I thought, Well I can do this, too. I am an attractive, accomplished woman, so now is the time to get out there and find that guy whom I deserve and deserves me. I crafted my online profile with seductive sayings such as: “Being Southern, I am very huggy and touchy, and say ‘sweetheart’ to everyone. Most importantly, I still rock the 6-inch heels at age 58!” Of course, I also posted the most flattering photos. I set my sights for men ages 50 to 65, with a bachelor’s degree or higher, a nonsmoker, and I had no preference for race, religion, height or weight.

Really, I was just looking to have a fun, intelligent conversation with someone, with hopes that chemistry might be there!

“It’s Not You and You’re Not Alone”   

The first hour I was online, I was rolling in the “likes” and felt as if I had just hit the Triple 7’s at a casino. I was thinking, This is great! In hindsight, I did not understand the game. Even though I did not engage with the young ones, I was excited when the 20- and 30-somethings hit me up. Come to find out, many of these people are not who they say they are. They are scammers trying to get in your pants or get your money by wooing you with sweet words. You talk/text with them for days and week. Then you hear, just when we were about to meet in person, something like this: “I have been robbed and I am stranded in Southern Chile, and can you please wire me $1,000 so I can finally meet you in person.”

I thought, Is this for real? I did think it was bizarre that a man who said his job was as an “antique dealer” in one of the most rural parts of South America, close to Antarctica — but hey, everyone has his niche. Well, I did not wire the money but felt foolish for ignoring the other men while I focused on this thief for almost a month — because I was taken by his looks.

More Lies, Lies, Lies

One thing I have learned about many online prospects is that they are really convincing liars. While I did not specify on my profile anything about height or weight, I did cite education expectations and, of course, expected them not to be married. I cannot count the number of “matches” online who claimed to be divorced but were living with wives and children.

The one date that always comes to mind is the man who lied about everything. He lied about his age, his education, where he lived, his marital status and his employment. Although the fake image he portrayed when I agreed to a phone call turned out to be so fun, I said yes to meeting him in person. On that first and only date, he came clean about everything. His explanation: “If I told you the truth, you wouldn’t have gone out with me. And I find you fun and sexy and I want to have sex with you.” 

I was, like, “WHAT?”

Sex, Sex and More Sex

This is a “hot” topic that could be written into a 500-page book. Let me just say that the “three-date rule” to wait to have sex does apply. You know if you have sex within the first three dates, then bye-bye. Or, if you do not have sex within the first three or so dates, then bye-bye. Well, usually. I know there are people out there who had sex early on and then ended up marrying. That was not me. I know many sex experts say that we are all adults and to go out and enjoy yourself. 

OK, I want to enjoy myself, but I would like to see you again! The first few months of online dating, I sure did not know about the three-date rule and, well, it was bye-bye more than a few times. I was devastated!  I started asking men who had been online dating for a while, and they said, “If I know I’m not going to get any sex after three to five dates, then I am moving on.” Again, I was, like, “WHAT?”

“All’s well that ends well. … Well, it ends”

As of this writing, I am not online dating and am taking a long time-out to focus on me. My son is in college, I am an empty nester, love my work and have many friends who I cherish. I am not worried about scammers, being ghosted, losing sleep or wondering if I should/should not have sex with a guy. While I do not discourage online dating — as I have met some nice men and had interesting conversations. Just remember that next time you hop online, look at it as like having lots of “one-and-done fun.”

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