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Single Parents’ Dating Disasters


Hey, it happens to the best of us—check out these hilarious stories of head-butting and worse, and know that you are not alone.

by Lambeth Hochwald

ou’re a single parent, and you’re dating. And sometimes you discover that being a single parent and trying to date just don’t mix so well. In fact, sometimes it seems like Cupid plus kids equals a recipe for disaster, or at least major embarrassment. Now, we all know true love can triumph, but in the spirit of “misery loves company,” read these funny tales of romance gone wrong.

Hitting him where it counts
“I once went on a date with a man who had a four-year-old son—just like I did—so we brought our kids along. The kids got along beautifully, and we were also getting along well. At the end of the play date, my son—who is not used to being around a man full-time—gave him a big hug, head first. Since my son
“My son totally head-butted my date in the crotch; it took my guy well over 10 minutes to recover…”
was roughly waist-high on him, he totally head-butted my date in the crotch. It took my date well over 10 minutes to recover, catch his breath and speak—and all the while, my son looked up at him adoringly. I was so embarrassed!”
—Sally Shane, 40, St. Louis

He blinded me with science
“I met a very nice guy online, but because I had my 12-year-old daughter living with me, it was hard to carve out time to meet him. We finally met for coffee, but I couldn’t find a sitter—and didn’t want to leave my daughter home alone—so I brought her along. It turned out that he was a science teacher at a nearby middle school. During the date, my daughter announced that she was studying for a science test. My new friend insisted on testing her. She demurred at first, but he was determined to get in good with her. He asked her what the test was on, and she told him it was all about sex hormones. I spent the rest of the date squirming behind my latte as he quizzed her on where testosterone was made, how many ovaries a woman has, what sperm is, etc. The moral of the story: Never introduce your daughter to a science-teacher beau!”
—Judy Lederman, 42, New Rochelle, New York

From the mouths of babes…
“As I opened the door to greet my blind date, my then seven-year-old twin daughters and four-year-old son stood behind me. Before I could say hello, one of my daughters stared at my date and said, ‘Boy, you look funny.’ My other daughter promptly chimed in with ‘Hey, you smell funny too.’ I glared at them and looked at my date with a smile and an apologetic, ‘Kids, you gotta love them!’ Then I grabbed my stuff and hustled him out the door—I wanted to get him out of there before another word was said. As the door shut, I could hear the giggles and the stampeding of feet as the kids rushed to the closest window. On our way to dinner, I apologized and tried to tell my date that the kids didn’t really mean it, but the damage was done!”
—Sammi Hines, 29, Baltimore

Star-crossed date
“When two single parents go out, you have to expect the unexpected. Need an example? I had planned to have dinner and go to a movie with the single mom of two kids, the oldest of whom is a teenager. We had a nice dinner and were planning to see a movie. When
“I was cutting my date’s steak into tiny little bite-sized pieces, just as I do for my son!”
we got to the theater, she called her daughter to see how things were going. The daughter’s boyfriend was hanging out with her and her younger brother, and, as it turns out, the boyfriend's parents had freaked out upon learning that the two lovebirds were left without any adult supervision. My date ended up apologizing profusely and asked me to drive her home. I was bummed but understood the situation. It was all for the best, though. About five minutes after I dropped her off, my cell phone rang. It was my babysitter calling from a neighbor's house. She had taken my children, a six-year-old girl and an eight-year-old boy, outside to look at the stars with my son's telescope and one of the kids pulled the door shut, accidentally locking them all out—so I had to run home myself. I guess the date just wasn’t meant to be!”
—Matt Ullman, 33, Lakeland, Florida

Mommy’s little bodyguard
“I began dating a guy I’ll call Dwayne when my son Travis, now 16, was two and a half. Dwayne was five years younger than me and childless. When Dwayne first kissed me in front of Travis, Travis bit him in the leg. When I finally wrangled Dwayne into attending a G-rated movie with us, my son threw up on Dwayne’s back when Dwayne was carrying him into the movie theater. My cousin, who was with us, ran to a nearby store and purchased T-shirts for everyone so we could attend the movie. None of this chased Dwayne away, believe it or not!”
—Lisa Cohn, 48, Portland, Oregon

Old habits die hard
“One evening, I went out with a guy my thoughtful friends had set me up with. We were dining at a nice candlelit restaurant, and we were talking about work, politics, religion and Broadway shows. I was enjoying myself; we were engaging in witty banter when I suddenly realized everyone was staring at me. Then I realized why. As I was talking away, I was cutting my date’s steak into tiny little bite-sized pieces, just as I do for my son every single night. Needless to say, he never asked me out again!”
—Anna Shah, 33, Poughkeepsie, New York


Lambeth Hochwald is a New York City-based journalist who specializes in trend stories and relationship pieces.
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