Chicago’s Oldest Singles Are Getting All the Action

Online dating over age 55 isn’t that different than going out in your twenties, a recent Q&A with five seniors revealed.

Illustration by Kyle Webster

Illustration: Kyle Webster

Call it kismet or Zeitgeist or something. I just learned in “Most Eligible Chicagoans 2013” that 20 percent of our local singles met their last first date on an online dating site. That same week, divorced lifestyle doyenne Martha Stewart, 71, blurted to the Today Show’s Matt Lauer that she joined Match.com to find someone to sleep with. 

Turns out the fastest-growing segment of users on Match is over the age of 55, accounting for 17 percent of the site’s users. It was a gift from the column topic gods.

To find out what the scene is like for people old enough to collect Social Security, I decided to round up a panel of single seniors. I spent hours on dating sites seeking sources, royally striking out but becoming strangely popular in various open-minded circles. (Now I just need to get off Senior People Meet’s e-mail list before my wife starts asking questions.)

Finally, through friend-of-a-friend referrals, I found five online daters over the age of 60 who were willing to dish:

  • Kay, 75, a real-estate agent who was married for 28 years
  • Clayton, 82, a former TV director whose wife of 53 years died in 2008
  • Stan, 65, the COO of a collection agency
  • Pamela, 63, a widowed retiree living in Old Town
  • and Eugene, 65, a high-school teacher.

For two hours in a hotel lounge, the quintet regaled me with their online dating sagas—after the bartender turned down the music, which was too damn loud. What follows is a partial transcript of that evening. Names have been changed to protect the innocent.

How is dating different at your age?
Eugene: It’s more complicated. People are thinking about retiring, and they want to be able to afford to get to their own grave, so they’re cautious. When you’re younger, you’re willing to roll the dice.
Pamela: You get a lot of health issues.

Why did you go online to date?
Kay: I had been divorced for a while and working hard, and I just wanted to meet people. The best thing about Internet dating for me has been the stories. I have friends that live for my stories. You know, “Tell him the nudist story!”

So what are your best stories?
Stan: I met this Palestinian woman on Match. Me being a Jew, I said all right. The first date was interesting. We seemed compatible. So we go to her home and we’re down in her family room on this leather couch, and she says, “My feet really hurt.” So I start rubbing her feet.

Ah, the old foot massage ploy.
Stan: Yeah. She had a black dress on, and then all of a sudden she spread the, uh, the Black and Blue Seas. She’d “forgotten” to put underwear on. We lasted six months. She wore me out.
Clayton: I’ll bet she did.
Kay: I don’t know how many men have assured me that they have Viagra.
Stan: I have a Cialis drip.
Kay: Sexuality at this age is interesting. I went out with a man a few weeks ago, and he told me how many women were after him on the Internet. He’s been a widower for two years, and he’s just in this fairyland. He said, “You could take me home with you.” I passed.

Is there a dark underbelly to senior online dating?
Eugene: There’s a bell-shaped curve of people. If you meet enough people, you’ll find nice people, strange people, unhappy people. Men don’t have a lock on being strange.
Stan: I got with this girl, and she started molesting me. I didn’t want to have much to do with her. I have to be very, very careful. You know, for viruses. You’ve heard of Navajo and Arapaho? She was a Wilmette Ho.

Do people lie about their age?
Pamela: Oh, yeah. Dark hair in the picture, but when they show up, it’s white.
Kay: One guy I met at Ruby Tuesday. After he sat down, he said, “I want you to know that if anything happens between us, I lied about my age.” “OK, you said you were 75. How old are you?” He says 85. Aged a decade in two minutes!

Do people still play the same games, like waiting two weeks to call?
Pamela: It’s the same. [One man and I] went out every weekend, but then he broke Friday night with me. I texted, “Are we broken for Saturday?” and didn’t get an answer. So I said, “Don’t text me anymore. I am going away.” Even though I was on my way to his house. It’s the same anger as when you’re 20.

Do your kids say, “Ugh, I can’t believe you’re doing online dating”?
Pamela: When I told my 21-year-old son I was on JDate, he didn’t know what it was. He said, “Why do you wanna date? You’re old.” I said, “Troy, it’s three years since Dad died. I’m not looking to get married now. I’m just looking to go out. I’m retired, I just want some fun.”
Stan: One last quick story. And excuse me for being a little risqué. Last year, I was going to Las Vegas with my girlfriend. I was at security, and I see the TSA stop the conveyor belt, call another guy over, and they start laughing. They tell me to come into this room, and search me, top to bottom. Then they start opening up my bag and found what I had in there.
Clayton: Which was?
Stan: Sex toys.
Clayton: Oh.
Stan: I’m 65 years old. And besides doing whatever I do, sometimes women need a little extra, uh, stimulation. The guys call the bomb and arson squad! I say, “It’s not a bomb. It’s sex toys!”
Kay: I’m delighted. You’re an inspiration.

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