Deb Lehman

Deb Lehman
Sep 01, 2025 · 9 min read

Looking for Mr. Wrong

Looking for Mr. Wrong


I thought I knew something about love after five decades of dating. What did I know?  Only that love still confuses this romantic realist or realistic romantic. It seems that the only place today to meet the largest pool of prospective Mr. Rights is in the not-so-brave new cyber-world of dating if you’re not a reality TV star or celebrity.


I’m back in the dating game as a sixty-plus and some things never change. The good news is that great sex is still possible. The bad news is that many men still want to fuck you instead of getting to know you. They text you at midnight before you’ve even met and think older women are so horny they’re willing to put up with anything for a hookup. Divorced men (and women) carry a lot of baggage. Their former spouses haunt them.


Joining a singles website takes guts. I’ve been on and off three sites over the past ten years. Let’s be honest. Blind dates have always been a crap shoot. If you make it past the first awkward phone call, meeting a stranger in person for the first time can be scarier. So many people lie about their age, weight, job, marital status.


But there are little white lies and big ones. Lowering your age by five-ten years or your weight by five-ten pounds, isn’t a deal breaker in my opinion. However, making yourself twenty pounds lighter or twenty years younger…saying you’re a successful entrepreneur or an overseas engineer on an oil rig when you’re an unemployed loser or con artist…or hiding the fact that you served time as a felon is just wrong.


Katie Love, winner of Writer Digest’s 2023 Personal Essay Awards for her poignant essay “Killer Punchline: Comedy-Tragedy in the Dating World,”  unwittingly dated a murderer who concealed his past. I can feel your pain, Katie, despite the need to laugh away the heartache.


Also, claiming singlehood when married or hiding an apparent sickness is delusional. Your date will find out sooner than later. I dated a middle-aged professor of media studies from Rutgers who sent me a video of himself on a talk show where he appeared attractive and energetic. I was psyched. Imagine my shock when I saw him shuffling to the restaurant like a geriatric. Get out of here now, I thought. You don’t owe him anything. He’s a stranger. But it’s mean to stand up a date at the last minute. And he looks so forlorn. He breaks my heart.. Well, I did the right thing, but it was impossible to talk because he shook so much. He must have had Parkinsons. You want a guy to shake your world not your table. Never again. The hell with being nice. Sometimes you’ve got to be cruel to be kind.


Every now and then you meet someone “normal” and date him for a month, a year, maybe two. These exceptions usually have something fundamentally wrong with them: hunched backs, huge heads, gambling addictions, womanizing. Most of the men on dating websites should come with skull and crossbones warnings: danger lurks here. Apparently this applies to some women, too, who post sexy pics and ask the guy—typically an older doofus—for money.


Here are several anecdotes to make you laugh and sigh. But there’s no crying in dating.


Hot-to-Trot John


John: “Hi, up for something casual?
Me: Hi John, you sure don’t sugar coat things…what is your definition of something casual?”


John: Friends with Benefits. What turns you on?


Me: “I’m not looking for a friends with benefits relationship. Been there, done that, in my twenties. Not looking for marriage either. Want something in between.


John: You still haven’t me told what turns you on


(Next)


 


Litigious Lawyer


“Let’s meet for ten minutes over coffee,” suggested this successful trial attorney who looked like Santa Claus with his long white beard and pot-belly. I chose a nice restaurant for our date. He ordered a glass of lemonade and asked for three refills. When I ordered a Bloody Mary with Absolut vodka, he said:


“Do you really think ordering Absolut vodka makes a difference?”


“Um, yeah.”


We talked mostly about the daughter he had lost to cancer and the grandson he was raising. He wasn’t interested in me.


“I used to run a love letter business,” I tried to lighten the subject and would have expected an educated man to ask: “Really? Like Cyrano de Bergerac? How fascinating.”


But no questions. Only a yawn. Who knew a litigator could be so dull and cheap? When he hugged me goodbye, I shrugged him off. Why would a man expect a hug after a lousy date? As if.


Love Bomber


Joe was a great cook but a control freak.


He wouldn’t let me into his kitchen. Not even to make coffee or a salad.


I also pride myself on my culinary abilities.


“The Italian olive oil from Costco is the only good olive oil,” he  declared. “Any other brand is inferior.”


“But I prefer the Portuguese olive oil from the Wine Library,” I retorted. His arrogance annoyed the hell out of me.


“You don’t know how to shop,” he mocked. “You spend too much on labels. And you don’t know the first thing about barbequing. I lived in Texas. I marinate my ribs for ten hours.”


We continued to bicker over such inane things until my sixteen-year-old daughter, intervened: “Step away from the phone, mom.”


He never complimented me except to say I was “hot.” He played guitar, sang the blues, had sartorial swag in spades, and the sex was fantastic. Surprise! I never had great sex with someone I didn’t like before. Joe was a moody bastard. He treated me like a princess on the first few dates only to drop a bomb several weeks later about his screwed-up mother who kept his father’s murder a secret for twenty years. Joe was a love-bomber: someone who gives you excessive compliments, attention, or affection only to manipulate you down the line. He was generous at first, but once he hooked me on the sex and the delicious dinners, he dropped the mask. I confused manipulation for decisiveness, but once I realized my error, I broke up with him. Via text. Don’t judge me! I was afraid he would undo my resolve with his amazing kisses. Sometimes texting is the only way to end a destructive relationship with a misogynist.


Fat Baldie


It started out so well. We had a wonderful first convo and I couldn’t wait to meet him. But then he ruined everything by sending me a picture that I never asked for. The photo showed eight hot men and one fat, balding guy posing shirtless on the beach.


Please let him be one of the hunks.


But to my dismay, he said: “I’m the fat balding one.”


No, you’re joking. I didn’t want to believe him so I asked: “You’re the one with glasses and green trunks?”


 “Do you see any other chubby Jewish guys in the picture?”


First of all, not all Jewish men are fat and balding. Secondly, why on earth would he send me a photo of himself standing neck-and-neck with all these gorgeous, ripped men? Did he expect me to say, I don’t care what you look like. I care what’s inside you? Sorry, call me shallow but I need to be attracted to a guy. While most people lie about their age or beauty to make themselves more attractive, this fellow did the opposite. Bizarre.


Despite the slings and arrows of outrageous dating—litigious lawyers, love bombers, and fat baldies—I still believe in love. Love in all its forms: sexual, romantic, familial, and platonic. I’m no longer a starry-eyed teenager who believes a man can fill the empty spaces of my soul, or fight my demons like a knight in shining armor. Unlike a needy serial dater I know who believes men don’t like intelligent women or wealthy men only marry trophies, I don’t need a man to define me. And I refuse to be used. But now and then, I need a tender hug or a mind-blowing kiss to feel alive. I’m still waiting for Mr. Right, even though I keep meeting Mr. Wrong. Hey, you never know. I’m a hopeful romantic.


 

© 2025 Deb Lehman. All rights reserved.