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A New Season of The Bachelorette Has Started—on My Own Computer

It's not the show on ABC. It's the real drama of a woman in her 50s jumping into the world of online dating. Joanna Bennett reports on all the men she's met along the way.

Sssh. Quiet. A new season of The Bachelorette is starting. This is the one in which they take a 57-year old separated woman and plant her in sweats before the flickering blue light of her MacBook Pro, watching as would-be suitors send “winks” and messages from the likes of OkCupid, Match, Bumble, Hinge, and JDate. Believe me, there’s no limo … no hairstylist … no help from Chris Harrison. All we’ve got here is one woman trying to navigate the world of middle age online dating, despite the fact that her last courtship took place in 1987 B.C. (before computers).

This is so not what I anticipated at this stage of my life, but when my 29-year marriage officially bit the dust a year ago … well, a girl’s gotta do what a girl’s gotta do. And though we all want our 15 minutes of fame, I think I’ll pass on being cast in a reality-TV dating show. Here’s why:  

  • I won’t be able to stand during those marathon rose-ceremony taping sessions, as comfort-shoe designers Clarks, Aerosoles, Naturalizer, and Born do not make stilettos.
  • The overnight dates could get awkward, what with my menopausal need for a bedside electric fan.
  • Any mention of “taped episodes” would actually refer to my hair extensions, which are the only way my fine, thin locks can look camera-ready and luxurious these days.
  • Surprise date cards would require a pause from the cameras to allow for a brief scramble to search for reading glasses.

And, so, without the assistance of ABC, I decided to go off on my own and enter the world of online dating. As I do any project—be it putting a magazine to bed, decorating a room, or making travel plans—I went in with gusto and an eye on the prize: I am, you see, the ultimate get-it-done girl. All of which explains why I didn’t sign up with one dating site: I signed with four of them.

I won’t bore you with the tedium of poring through hundreds of profiles (I’m fast—it’s not unlike flipping samples at a carpet store), but when the messages started flooding my inbox, I began to second-guess this adventure. Case in point: My First Impression Rose (NOT) goes to a bearded, grizzled-looking 60-something who sent the following note:

Hello, My name is Bill you don’t need to look in the freezer reviewed like to have coffee LOL maybe I’ll hear you put a good package together take care there is always light at the end of the table and we must be positive that the person make him more so every bit of reporters of seltzer.


Undeterred, I narrowed my list down to seven or eight seemingly smart, charismatic, good-looking (sane?) guys, with whom, over the course of a week or so, I exchanged great messages. I then showed the pics to a select group of friends and relatives on the premise of wanting feedback. (But actually just to gloat about all the dates I had lined up.) Next thing I knew, a few of the poor souls were being voted off the island by my protective clan before they’d even bought me a drink. The guys immediately got labels: Intellectual! Standoffish! Smiley Eyes! Cancer Researcher! Triathlete!

Whatev. I forged ahead with my adventure. Here’s all the types of guys I met during my online dating over 50 adventures. 

Read More: The Upside-Down World of Online Dating After Divorce

He said he was 60, but his photo made him either a freak of nature or one of those dudes who puts up a ten-year-old, outdated corporate business portrait. We chatted a bit. He gave up his LinkedIn profile, and I saw that he grew up with a friend of mine. So he fell into the safe zone, and we met for a drink. From our conversations, he knew I’m Jewish, and though he’s not, he was able to cleverly banter about shiksas and bagels and schmears with the confidence of Mrs. Maisel.

I arrived at the bar first, quaffing my wine in a semi-state of disbelief that I was even in this situation, when Gent sauntered in. Two things: Yes, it was a ten-year-old outdated corporate business portrait. And, yes, he knew how to talk “Jew,” as his opening line was to playfully come up from behind and whisper in my ear, “Hey, are you the beautiful blonde who’s not a Shiksa?” He got major icebreaker points, and we were off. Not to a land of romance—because it was clear to me that Gent was more like an older brother and clear to him that I was about one minute into online dating—but to the solid friendship zone. To this day, we text, we banter, we skewer the president, and I run occasional love quandaries by him.

Smiley Eyes

One of my love quandaries included this man, who sadly cancelled our date before it even took place. It seems Smiley made a connection with another woman he met online and didn’t want to spread himself thin. Extra points for decency and honesty, but a big, fat bummer, because we had the best back-and-forth messages and a tremendous number of shared interests (Nashville, James Taylor, skiing, kids the same age, sense of humor … the list goes on). I told Smiley to touch base if his new flame burns out. He texted me back:

Appreciate your understanding and kind words.  

Would love to reach out if this does not work out … but am certain you will be completely head over heels w/ a very lucky and caring guy (also pretty sure your future looks very bright in a very happy place).

If ok, I will check in from time to time (rooting for you), and please do the same!  

Yes, please, Smiley.

Rhymes With Cad

I should have heeded the Red Flag when he called me by the wrong name on Bumble, but he swore the message was for me. A confident (cocky) and highly successful twice-divorced attorney, Cad was off to Hawaii for a week and booked a date with me for the day after his return. Meanwhile, he called daily from the island of Maui, often while babysitting his three-month-old grandson: He was impressively unruffled with the inconsolable infant bouncing on his chest. When we met for dinner, I soon saw why he wins every case. The guy was intense, good looking, and medicine for a bruised ego. He held my hands halfway through dinner, fed me sips of his Ketel One martini, planted a swift (surprise) kiss on my lips as he returned to the table from the restroom, and gave me earrings he bought in Hawaii.

Cad told me if he had two days left to live, he’d marry me instantly. I think at this point, we were on Red Flag #7. 

The words too-much-too-soon kept ringing in those adorned ears, but I was enjoying being swept off my newly single feet. He had to go to LA on business, and he made sure we had a 12-hour date on the books upon his return. Cad called me from the airport to say goodbye and told me he’s utterly smitten—and that if he had two days left to live, he’d marry me instantly. (I think at this point, we were on Red Flag #7.)  When I reminded him that I’ve just started dating, he became audibly dejected, almost pouty. And then … radio silence. Three days later, I received the following text:

Hey—I ran into an old friend in LA this week and we kind of re-hit it off again. So I guess I’m officially off the market and we are at different places in this thing. You are a neat person. There is some lucky guy out there. We can talk on the phone if you like. Totally up to you.

I didn’t like, and I never answered him. Forget the new girlfriend, calling me a “neat person” sealed his fate.

Stanley Tucci

My next date was with a charismatic, whip-smart, New Yorker—and doppelganger for the Devil Wears Prada star. (In fact, I believe he was wearing Prada.) But let me just say that the real actor is 5′ 8”, and when his brother-from-another-mother stood up from our restaurant table, it became clear that Stanley was the tall one. Height aside, I could overlook the fact that he was in weed marketing, but I couldn’t overlook the fact that he has a young child, was formerly married to a model, and reserved Wednesday nights for sex with 20-year-old women he meets on Tinder. In all candor, my cellulite-dappled ass would likely not survive the humiliation of getting naked with a guy whose usual conquests are willowy, 5’11 millennials. (And btw, what the fuck????)


His first communiqué came while he was on a surfing trip in El Salvador.

Athletic: Check!

He wrote me about his job as a leading cancer researcher.

Educated: Check!

He suggested oysters and dirty martinis at a restaurant I’ve always wanted to try.

Fun: Check!

He made reservations for us.

Chivalrous: Double Check!

As it turned out, the place didn’t take reservations—he accidentally made them at a restaurant of the same name, some 3,000 miles from our town. (Points for trying.) But we met up for a drink and a meal at an alternate pick and enjoyed easy banter, a love of good food, and decent chemistry. He texted the next day and suggested getting together again later in the week; whereupon, I never heard from him again.

Asshole: Check!

Hiker Guy

We met for margaritas, and as I went in for a hug, he literally recoiled. Winner of the most awkward greeting of 2018, I concluded this was because he was shy and uncomfortable with physical affection, and I immediately declared him toast in my mind.  As it turned out, he was shy … but in his defense, he was also hiding a bag of Flamin’ Hot Cheetos under his coat, a courting gift since I mentioned my passion for these finger-staining snacks in my online profile. I decided to give shy guy another try (hiking, a few dinners, pool, bowling, even awkward sex), but it soon crashed and burned as he (wisely) realized I was just not that into him.

Read More: First Love Late in Life. Yes, It Happens! Here’s Proof

Curtain Call

A theater producer was up next. But seeing as I’d lived and breathed musical theater for 30 years (ex was in the arts, and son is a Broadway director), I was skeptical that I wanted an orchestra seat to a show I’d attended over and over again. Plus, he had an 11 year old and a 16 year old, one of whom was … let’s just say, “challenging.” And since I was currently seated in Act Two of The Empty Nest, I was looking for a plot that included travel, not tantrums. Exit stage left.

Nice Jewish Boy

Wait, what? I’d been rejected before we’d even met … AGAIN?

Okay, now we were getting somewhere. Only he didn’t eat pork or shellfish, and I consider bacon not only a major food group but also the largest section of the food pyramid. On the plus side, we had two mutual friends, and when we talked on the phone, he had the sexy the voice of a radio announcer. NJB and I made a cocktails-and-appies date for the following week, which would not include pigs in a blanket because, in addition to the pork thing, it was also Passover, and he was not eating bread. He had a quick wit and our banter got kinda saucy over text. This gave me hope that his conservative stance didn’t extend to other areas of his life.

Three days before the date, I received a text in which he very considerately told me he started seeing another Jewish woman with whom he felt a strong connection. Insert flattery: “I wanted to give you as much notice as possible. I’m sure you’ll have no trouble filling that Friday night with other gentlemen suitors.”  Wait, what? I’d been rejected before we’d even met … AGAIN? (This was key, ladies, so listen up: Book the date and go out ASAP, as you are literally competing with the woman who gets the slot the hour/day/week before you.)

As predicted, when NJB and his new girlfriend imploded, he rescheduled our date and made it clear he should have gone with me in the first place. Yes, he was handsome, funny, smart, and nice. And my heart was thumping, only—plot twist here—it was not for him. Why? Because Smiley Eyes was back. And after only one cup of tea together, I knew—the way you know something from your head to your toes—that he was the one I was supposed to be dating.

Spoiler Alert

I mentioned this to Gent, my dating guru, who, when he heard Smiley’s last name, went bananas. “Wait …THAT’S the Smiley we’ve been talking about for two months? I’ve worked with him for over 20 years. He’s the greatest guy ever!”

He was 100 percent right.

Yes, Smiley has the kindest, warmest eyes and a grin that will melt you. But he’s had me smiling for six months now—like, crow’s feet and marionette lines have actually etched deeper into my face thanks to my sweet guy. And I don’t care a whit. I don’t think he does, either. And that’s just one of the reasons (spoiler alert) that I’ve fallen in love with him. Remember how his original cancellation predicted I’d be “head over heels” in a very happy place? Turns out, Smiley is a fortune teller, too.

Mind you, I haven’t fessed up to the love thing yet … because hell if I’m going to be the first one to put my cards on the table and expose my vulnerable heart. But Smiley is cautious and careful and doesn’t want to rush our relationship. And while he may not have said the words yet, he shows me how much he cares about me every single day: He’s fine with my taped-in hair extensions, my comfort shoes, my reading glasses, and he’s even willing to sleep in long-sleeved pajamas just so I can turn the fan up to high at night. If that isn’t love, I don’t know what is.

Online Dating Over 50: Pinch Me

I am still bruised, but it’s no longer from the pain of losing a 29-year marriage.

Moreover, he treats me like a princess. He is caring, kind, generous, loyal, fun, calm, soothing, easy, smart, inquisitive, athletic, and one of the most decent men I’ve ever met. He doesn’t bring me Cheetos because he knows they’re unhealthy. But he does make me dinner, hands me cocktails in the shower, rubs my feet, turns on James Taylor, laughs at my overly long stories and basically makes me feel taken care of in a way that I haven’t experienced in decades. It’s exhilarating … and terrifying.

I am still bruised, but it’s no longer from the pain of losing a 29-year marriage. I’m bruised from constantly pinching myself, wondering how fate led me to click on the profile of one of the best men I’ve ever met.

I hope ABC doesn’t mind, but I’m bailing on the rose ceremony for now. Smiley makes me feel like a rose. And that’s the ultimate prize.

Stay tuned.

Read More: As If Dating at This Age Isn’t Hard Enough: How About Virtual Dating During a Pandemic?

A version of this story was originally published in October 2018. 

Further Reading

101 Protocols for Online Dating

121 First Dates: How to Succeed at Online Dating, Fall in Love, and Live Happily Ever After (Really!) 

Bachelor Nation: Inside the World of America’s Favorite Guilty Pleasure

By Joanna Bennett


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