single parent dating


I’ve been a single mom since my son Jack, 7, was in my belly, which means my dating life gets, well, complicated. When you’re a single parent, dating is part challenge, part comedy routine. It also feels like deja vu all over again. In fact, most of my single mom dating scenarios remind me of what it was like when I was dipping into the dating pool as a fresh-faced teen. Here’s why:

Fooling around is still risky business.

When I was a teenager my mom caught me making out on the living room couch with my boyfriend Joey*. She was probably more embarrassed than me and gave a loud cough as a signal to stop kissing and get back to studying. Fast forward: My sleepy son wandered out of his room — to pee — and caught me making out with a guy I’m casually seeing. This time I was the one who was more embarrassed. After Jack peed, he decided to join us for a cup of milk. Then and now, my makeout sessions get sabotaged. Busted!

I still have a curfew.

Back in high school I was always rushing to make it home by my 11:30 pm curfew to not piss my dad off — and risk being grounded. It’s not so different these days. If Jack isn’t sleeping over at grandma’s house, I’m rushing to get home so I don’t piss my sitter off by being later than expected — and risk losing her. And honestly, at 12 bucks an hour, I don’t want to break the bank.

I’m still a pretty (good) little liar.

I admit it — I lied to my parents a few times in high school so I could hang out with a guy or go to a club in NYC. My go-to lie was: Mom, I’m sleeping at Melissa’s*. And Melissa told her mom she was sleeping at my house. Well, I’m still lying to my parents about where I go sometimes. Why? Because I don’t feel like telling them about every freaking Tinder or online date I’m trying, because I don’t want to play 20 questions just because I swiped right — and um, all I know about the guy is he’s 36 and had on a blue shirt. I usually say I’m going to a movie and drinks with girlfriends or a book signing in NYC. But I never date without a safety net. My cell is always on me and a good friend always knows who I’m really with and where I am just in case….

I still slink home at dawn.

OK, so I wasn’t doing the walk of shame at 15, but when I was in college I definitely dragged myself back to the dorm in the wee hours with last night’s makeup on and a wicked hangover, and promptly crawled into my skinny twin bed to crash. A few years ago I was dating a sexy, older guy who lived in Hoboken. I fell hard for him and never turned my family down when they offered to take care of Jack so I could have a grownup sleepover. Wining, dining and uninterrupted sex was ahhh-mazing, but then morning came all too quick. As a devoted single mom, I couldn’t just relax in bed, have bagels and coffee and then have morning sex (well, sometimes there was time for that). I would set my alarm for 6:30 at the latest, kiss my sexy guy on the cheek and tiptoe down the stairs in his T-shirt and my jeans or mini skirt, in heels (ugh — heels on cobblestone!) and a topknot. There I was — in my 30s making a mad dash to the car so I could toast waffles and watch cartoons with my kiddo.

I still have to get creative to get busy.

When I was in high school, Joey and I would make out in his car on the top of the parking garage at the mall. After getting caught fooling around at home (see above), it seemed like a good idea. Let’s just say, dates have parked around the corner from my house before dropping me off. I’ve been swept away to a hotel after dinner for a few hours. Sometimes I don’t eat lunch … on my lunch break.

Infatuation is still a thing.

I was one of those girls who went gaga for guys and talked about them, wrote about them and daydreamed about them nonstop. As a single mom, finding a cool guy who likes kids and is not a sociopath is a big deal. So I’ve definitely texted my girlfriends about how awesome Ken* is. I’ve imagined marrying Ken and my son calling him Dad. We have another baby. We live in a home with a Spanish style roof. Dating is a huge, exciting deal for a single mom! You want to scream it from the rooftops!

Breakups still really, really suck.

I was a teen drama queen when it came to breakups, and that hasn’t changed since becoming a mom. Dating as a single mom requires so much time and planning and organizing. When you lose the person you spent two years loving, trying again seems like such a project. But there’s a silver lining: Taking a break from men is often just what the doctor ordered. Dating is so much work I never rush into a rebound relationship. And there’s hardly any time to mope, because you have a kid to take care of and baseball games to attend, lunch to make, homework to do. Being a single parent actually makes for a better breakup.

*Names have been changed to protect the innocent

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For more on single parent dating, including single dad Eric Elkins’s hilarious dating disaster story, check out Singlewith’s romance page. And for more on the subject of how trying to date as a single parent is like dating as a teen, go over to Wealthy Single Mommy, aka Emma Johnson’s great blog, for her take on the subject.

Photo by Karsten Winegeart on Unsplash