single parent


“Hey, are you dating anyone right now?”

I was at my four-year-old daughter’s baseball game watching my daughter play with another little girl. The other parents and I spend three to five evenings a week together at practices and games throughout the spring and summer, so we all get to know each other pretty well. A week earlier, I’d been talking with a mom who asked me what I did for a living. I told her, “I’m a writer. I write about parenting and dating/relationships as a single father.” In a different crowd, this honesty opens up the door for people to ask me a million questions and help them solve their problems while I’m out and about; but I digress.

At this last game, this lady who I have gotten to know over the last three seasons asked me the dating question. I thought back to our conversation last week and assumed the questions that I normally get were about to fly. So I was honest and said, “Not right now.”

She responded with excitement, “Oh really? I have this friend…”


“She’s thirty-six and has a son about your nephew’s age…”


“She’s a nice person…”


“She hasn’t really dated much since she and her son’s father broke up. I feel like she’s afraid to venture out, so she kind of keeps him around. I’m gonna give her a call right now!”

Shit! Fuck! DAMMIT!”  

I’m just not that into it

It was as if she ran down a checklist of everything that doesn’t quite work for me at this point in my life (I’m twenty-nine, I still want to have more children, and everything else just sounded like we wouldn’t be a good fit). I looked at my phone, and said, “Hold on, I have to take this call.” I walked away for a good five minutes, listened to a song and rapped along with the lyrics to look like I was having a conversation, and then came back. She had just got off the phone and looked like she was looking for me to show some semblance of interest. That’s when I said, “Honestly, I just got out of something I had been in for two years,” which is half-true. It looked like she took that to mean I wasn’t dating right now. Luckily, that was the last game of the season, so I won’t see her until next spring.

That was the moment that I realized that I’m that person people feel like they need to hook up. Honestly, only women friends who are more like associates do this. I like to think I’m pretty good-looking and I’m always coming to my friends with some hilarious and drama-filled dating story, so they don’t even try.

I am a single parent. I don’t have much time to be out and about to meet people. Others, like said baseball mom, see me spending so many evenings at games and practices and probably think I am inundated with doing things that revolve around children. And it’s very true. People are just trying to help two people they know who they think are good people. No harm, no foul.

OK, I admit it – I’m shallow

However, blind dates almost never end well. The first question anyone asks after, “I have a friend” is “What do they look like?” Often the response is “She’s cute,” or “She’s nice,” which all mean, “Hell no.” I have humored this once or twice and upon meeting the “cute friend,” I want to punch my  so-called friend in the face. Some may think this is shallow, but the truth for most is that physical attraction comes first, so I don’t feel bad at all about this. The truth is, you can ask someone who is a real friend of yours, “What does he/she look like?”And 9.5 out of 10 times they will respond, “They don’t look like someone you’d date.”

What happens when things don’t work out? It can get awkward. Everyone might be at a function after things went south. Or you could wind up losing a friend. While I do love being in the same place as one of my exes for the sake of a great story, I don’t need extra drama.

Sometimes people who want you to meet their friend think that you’re lonely. Sure, things would be a lot easier if there were two of us raising my daughter, but I am happy. I like to think that many of us single parents live pretty regular lives with the exception of our dating lives…that’s where things get incredibly interesting. And speaking for myself, I want to be the one to set up that part of my life. The acquaintances who want to introduce me to their friends only know me as fairly mild-mannered guy who does kid shit all day. If the baseball mom knew what the dating part of my life looked like, she wouldn’t think her friend and I were a good fit at all.

Readers, tell the truth: Do you like being set up on blind dates? 

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Photo by  Jude Beck on Unsplash

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

This New York winter has been brutal. Mr. Groundhog found his shadow and indicated there will be six more weeks of winter, but he didn’t let us know we’d be in for record lows and everyone getting sick. As February inched into March I too started sniffling and sneezing, and I had a splitting sinus headache the other day. I decided to do something I normally don’t: lie down.

It was a weekday afternoon right before all of the good shows come on ESPN, so I found myself watching Friends. I have seen every episode so many times that within thirty seconds I can tell you which episode it is.  The other day I once again relived the story arc in which Rachel gets pregnant and doesn’t want to tell Ross. Shortly after he finds out, Rachel goes on a date again and Ross freaks out (sounds like every episode from the first four seasons but yeah…). Ross is sitting with Joey and explains how he thought that the next time he became a father, life would be different. I hadn’t seen this episode since becoming a single parent, so it kind of hit home.

Ross goes on and on about how after his first marriage didn’t work out, he had this picture in his head of what he thought his future life would be like. He would be married, they would be a family that was together – not a blended one. That made me think about when there was once a picture in my head…

All while my daughter’s mother was pregnant I told her that within eighteen months of our first child being born she would want to do it all over again. She didn’t believe me. Then September 2011, about seven months after Cydney was born, she’s staying at Roswell Park Cancer Institute in Buffalo, New York, being monitored for a few days while undergoing aggressive treatments for terminal cancer. I had just gotten off work and went straight there. She did me a solid by letting me watch the Yankees game and a commercial came on about children. With just a little bit of hair on her head growing back after her chemo treatments being changed and weighing about eighty-eight pounds she said to me, “I wouldn’t mind having another child now.”

I responded with a laugh and said, “Damn, I gave you eighteen months and you couldn’t even make it eight!” She laughed and externally that was the end of the moment. But that was the day my picture changed. Being that she was undergoing chemo, there would be no more children from her. I knew that. I’d had flashes of what the night she passed away would be like, all while looking at my daughter like, “Hey, it’s just you and me and we’re gonna just make sh*t happen.” At the same time, while I thought it was a long shot, I always had faith that one day she would be all right and she, little Cydney, and I could be a regular family in the end, with an amazing story to tell. Somehow, hearing her express a wish for a second child, for that perfect picture, was my confirmation that one day the woman I loved and the mother of my child would leave us.

Going back to the Friends episode, Joey asks Ross: When he sees that picture, is Rachel the woman?  Ross responds he used to think so, but at this point that person no longer has a face. I play around and pretend that I’m going to be a single dad/bachelor for the rest of my life, but even George Clooney got married so but I don’t that’ll be me forever. I have seen a face before. I have pictures of the three of us together and it kinda looks like we’re a family. Somewhere between being a cynic, realist, not wanting to count all my eggs before they hatch, limbo, and faith I try to see it as nothing more than that, for now.  At twenty-five years old I learned what most don’t until much older in life – that there are no guarantees and tomorrow isn’t promised.  While that family of three is what I see and I want, and I’ll pursue that by all means, I’ll also just enjoy the ride. The picture could change.

All of this is to say that almost no one envisions themselves as a single parent. Whether single parenthood came to us by divorce, artificial insemination, adoption, loss, or whatever; no one thinks about themselves raising a child on their own.  We aren’t wired to have that picture in our heads. It’s a bittersweet dream deferred but you love it, nonetheless. Sometimes you need that picture in your head to be the driving force and the reason you don’t give up…even if it doesn’t turn out the way that you’d like it. We all need something to aspire to.

In the meantime, the ones with us and the child(ren) we love dearly are amazing enough.

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Photo by  Matthew Ronder-Seid on Unsplash

When my son started kindergarten this year, I set a goal to make more mom friends. Since he’ll be at his school for six years, I want to really grow with him and put down some roots in the school community. So far I feel like I’ve been somewhat successful. I’ve attended parent meetings and volunteer events, which is great because I keep seeing the same people and it feels like we’re laying the groundwork for friendship both in and outside school. As fulfilling as that feels, it’s also made me realize the importance of continuing to grow and build relationships with non-mom friends, too.
Last month I celebrated my 30th birthday and I spent the day with my son and my BFFs, neither of whom have children. And let me tell you, it was perfect. We went to the beach, rented a cabana and just chilled. We brought food, wine and books to keep us busy. We took selfies, and celebrated another year of life and friendship. I watched as my son built castles, wet his feet in the water and and threw sand in the air. I knew he was having a good time too. Single mom, child, and single girlfriends – we weren’t your average birthday celebration gang, but it was heaven.
I need my non-mom friends just as much (if not more than) as mom friends from the bake sale committee. Let me count the reasons why:

1. Even though it scares the shit out of them, non-mom friends don’t mind babysitting.

Like the cool, child-free aunt, my best girlfriend has babysat for me on a number of occasions when I have to work. Each and every time, she comments about how she “doesn’t know what to do with a kid,” and I gently remind her that most days, I don’t know what the hell I’m doing either. Turns out we both know way more than we give ourselves credit for.

Non-mom friends find the best, cheapest fun stuff to do for just us girls.

When I’ve got a kid-free weekend, I know I rely on my friends for a really good time. First off, they’re way more flexible time-wise and can rejigger their schedules to fit with mine. And they come prepared! They always dig up the best Groupon deals and scour reviews for the best new restaurant. We go to art shows, free concerts in the park, bookstores or just sit in coffee shops talking and catching up. We can hang out all day and stay up all night, since nobody has a curfew or has to put the kids to bed.

Non-mom friends help you to remember to take care of yourself.

This is so, so important. As a mom it’s so easy to get wrapped up in parenting the little ones that you forget you need some care and feeding too. And that time off from your kids makes you better parent when you’re with them. My non-mom friends remind of this fact often, and I am grateful for that. They also have stories of the days that seem so distant, when we were undergrads with no other responsibility except getting to class on time, or whip out an old photo of us at a college bar. They’ll call me out when I’ve worn my yoga pants too many times on our nights out, or remind me how beautiful my eyes are when I wear eyeliner.

Non-mom friends give you a different point of view.

My non-mom bestie is the one I turn too when I need someone who can really listen or give me a shoulder to lean on. I mean, can anyone have a conversation when you’re both yelling at your kids or trying to break up a fight between siblings? Just because my friend doesn’t have children doesn’t mean that she can’t give good advice. She draws from her own experience with her mom, her friends’ moms, and the moms she know. Because they’re not in the trenches, my non-mom friends can look at things from a different point of view, which is often refreshingly honest and practical.

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Photo by  Leighann Blackwood on Unsplash

I often am asked whether or not I would consider getting married again.  For a long time, my response was something like,  “I’d love to.  But to be honest, I think I’m going to do a George Clooney it and be a bachelor forever.”  But Clooney got married, so I replaced him with someone else who’s made a career of being a single guy — Derek Jeter. Then he got engaged to model Hannah Davis, something more unlikely than the Yankees captain being honored by the Boston Red Sox, archrivals beat the Yankees in the 2004 World Series, when he played his final game in Fenway Park and retired his jersey.

My heroes are failing me…

Actually, it’s quite endearing.  Men who once had committed themselves to not being committed seemed to have found someone who complements them so well that they want to finally settle down.  For the most part, that’s what everyone wants.  It’s what I want.

Been there, done that

However, I think about the many conversations I’ve had with my single friends who are tired of dating and think happiness is finding someone they’ll fall in love with forever. But having the traveled the road from great first date to saying “till death do us part,” I find myself putting them on game on how this life partner deal really works — the overwhelming odds are that they are going to get on your every last nerve.

They will try your patience in ways that will surely make you do things you swore you would never do andpromised them you wouldn’t do back when you were dating.  You will consider — and probably carry out —acts that your partner once said were deal-breakers because you know they actually won’t be. You will dread knowing everything they are going to say before they open their mouth. But they are still your best friend and you love them more than anyone else on the planet.

“But I don’t want to compromise!”

I can’t lie, I actually miss that.  However, just thinking about all that comes along with it makes me more than a little wary to want to settle down again.

Perhaps my biggest phobia about commitment is the idea of co-parenting.  I have been a single father for almost five years and I know almost nothing about sharing parenting responsibilities.  Even while Cydney’s mother was alive, I stayed up all night, cleaned the bottles, and did most of the work. She passed away when my little girl was only nine months old.  For better or worse, all I know is being a single parent.  There is a good chance that part of my wanting to play the field for the rest of my life and have relationships that don’t last forever is because I am not used to accomodating someone else’s parenting ideologies and compromising on things like what school my child goes to and a million other things.  It has never been a part of my or my daughter’s lifestyle.

The pressure’s on

But Cydney wants me to have a serious girlfriend and get married. She wants a stepmother and siblings.  In fact, she says I need to do all of this by next week.  As stressful and draining as it can be sometimes, I love being my daughter’s everything.  Maybe this is the one part of my life where I want to and feel like I am justified for being a little selfish.  But I guess if George Clooney and Derek Jeter can find people worth committing to forever then maybe I can do the same.

In the meantime,  I still have Jamie Foxx.

DID YOU LIKE THIS POST? Please go to the Singlewith Home Page for much more, and sign up for our weekly newsletter in the box (above, right)! You’ll get great new essays, advice and ideas by and for single parents, coming to your email inbox. Also, register for our Singlewith Forums, to become part of our community and start connecting and getting support from fellow single moms and dads. Like us on Facebook. Follow us on Twitter (@singlewith) and Instagram (singlewithphotos). In short, JOIN US!

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