Dating Single Parents: Can it Work?

by mssinglemama on September 27, 2008

And now here I am digesting all of this advice…

and have found that it’s clouding my gut. My gut says, “You know your son and you know yourself and this wouldn’t harm him in any way.” But my head says, “You shouldn’t do this because the rules say you can’t.”

For those who think a night of camping with a new person would be absolutely selfish and catastrophic I ask – what are your personal experiences? Does one bad experience in introducing a man to your children mean you should isolate yourself from others forever?

What about other single parent friends who come and go? Do you keep them away as well?

Do you feel like, in the name of protecting your children, you may actually be hurting them by denying yourself your own happiness?


And I want to hear from more of you lurkers like Amy in Sedona. Sign in anonymously if you want…

UPDATE: Read about how my trip to visit Cabin Man ended up. Was Benjamin permanently scarred?

{ 2 trackbacks }

Single Minded Women » Blog Archive » Is Becoming a Single Mom the Latest Trend to Hit Hollywood?
September 28, 2008 at 8:56 am
Cabin Fever, Part 4
October 6, 2008 at 4:53 pm

{ 35 comments… read them below or add one }

liv September 27, 2008 at 12:04 pm

okay, so i’ve gone a little bleary eyed from the debate, but since i see a man who lives in a cabin in the woods, i’ll weigh in. the only reason my kids ever met him was because a terrible tornado destroyed his house, truck, and boathouse in May of this year–he needed some help, and i couldn’t always get out there without the kids. the only reason i continued to let my kids be around him is because he is the height of respectful to me– we don’t do the touching or the kissing or hugging in the presence of children. he talks to them as individuals. he is appropriate. the thing that separates my sitch from yours (it sounds like) is that i don’t have designs on this being a temporary relationship. i think that the kids of divorce collectively go through enough. my job is to keep my bf out of sight enough so that the kids still know they are first, even in the face of other people not doing what i believe to be ultimately right for them. (fwiw)


Modern Single Momma September 27, 2008 at 12:07 pm

There is the letter of the law and the spirit of the law. Rules are the letter and there power is fear, not love.
Your intuition is the spirit of the law and it comes from a place of love. In my opinion, this is what you should go with.


I am having my own issues though on whether or not my son should be seeing MiO in the “daddy” light just yet… all this is so complicated sometimes.



mssinglemama September 27, 2008 at 12:10 pm

Liv –

I’m glad you commented and shared your story.

This guy lives 2.5 hours away – it’s why I can’t see it turning into anything serious – as for the temporary, it may or may not be, time will tell. But I know we are definitely friends and I know he would respect me in front of his kids and mine.

The good thing is that because he lives SO far away, he’ll never, ever take precedence over Benjamin. No man I’ve had in my life thus far ever has.

Kris, for example, we dated for nearly a year (on and off, sure) but he never had the priority over Benjamin. So I’m confident in my ability to keep Benjamin very far away from any dating drama.

And I should add to this as well…

If I ever saw that a relationship or an introduction was hurting my son I’d drop it like a dead fish. As I think all single parents should. It’s our responsibility to protect them but sometimes this guilt and these rules may be too extreme.


mssinglemama September 27, 2008 at 12:15 pm

Morgan (aka Modern Mama)

See – your situation is totally different because you are madly in love.. and yes, it’s very, very hard. You’re moving in together too – but you’re trusting your gut and your going with what your heart is telling you.

Very brave and yes, very risky for Lucca. BUT, you will be there for him always – you will be able to pick him back up and yourself if god forbid – it doesn’t work out.

My advice: be careful on the Daddy thing so quickly because it could freak the man out. There’s no need for that yet. Your situation, like all of them, is unique and he’s actually been staying with you these past few weeks – but try to treat him as a friend in front of Lucca.

You two have been just fine without a man around for quite some time. Don’t lose sight of that.


Abran February 4, 2015 at 2:08 am

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Laura September 27, 2008 at 12:56 pm

I have several thoughts since you asked. I wouldn’t throw in the towel since you clearly like this guy but I would try to work around the issue by coming up with some alternate strategies.
Perhaps he could borrow or rent a car to come visit you on a week night? Perhaps you could go to visit on a weeknight on a day you have off the next day? Perhaps his parents could watch the kids on a Friday or Saturday so Dad can go out on a much needed date night? Perhaps he can make alternate arrangments with his ex and only have the kids for one night on a particuliar weekend? I think a relationship with cabin guy will take work but it is totally doable if you’re both willing to make that effort.
That said, I think the next move/visit needs to be his because he needs to show you that he is capable of making the effort and doing the planning. If it all falls to you in the early stages, it doesn’t bode well for the the future and it also makes things way too easy for him. I would also talk to him about his car situation and if that will be changing anytime soon because obviously that will come into play if you are going to be seeing him on a long term basis.
I would still stay away from bringing the kids into this right now. You don’t know each other all that well yet and kids do get attached very easily. A few months down the line after you know where you are headed with each other, I think it would be fine but give yourselves some time to get to know each other first.

Fingers crossed for you!


McSwain September 27, 2008 at 1:21 pm

If you’ve decided already it’s not going to be a long-term relationship, then what’s the point? Sounds like you’d be setting everyone involved, including yourself, up to get attached, then hurt. A camping trip sounds like fun, but fun is not always the best option.


Cheryl September 27, 2008 at 3:27 pm

Hi–I’ve been a single Mom for over 7 years. Dating has been interesting. I still have three at home (8, 10, 13)and the few times I’ve introduced them to someone I’m dating was because I thought the guy had potential. However, I met my fair share of “scaredy guys” as I called them. They were new to the dating scene, post divorce, and we afraid of all sorts of commitment. So, years ago, I just tried to make those sorts of things work, excluding my kids and just dating on my two free weekends. Insane. I finally just STOPPED. I’d rather not date if I couldn’t have a REAL relationship.

I think that you have the right idea here. Cut out if you have the slightest bad feeling about something. Instinct is big. If he doesn’t have a CAR…something’s wrong right away. No car? How does he get his kids around? Three years post div and not quite ready to introduce the kids? It’s not rocket science. Kids are smart–and if you do things right (no sleeping over, no intense stuff), they will be comfy.

7 years after divorce and after giving up dating for the most part, I stumbled across a guy who is everything I looked for and never found. Handsome single Dad of two boys, 12/10. Outstanding partner in all ways…even helps me clean in the kitchen when we cook together. My kids ADORE him and I adore his as well. We are solid. We see each other right now every other day. Leaves us both time to still make it “not too fast” but get the kids used to the fact that we’re a couple. They love it. I love it. It took so long to come across someone like this. I had faith but just stopped searching and he appeared. haha. I also stopped cold turkey with the “dating the wrong man and making excuses for him” thing.

Kudos to a great blog!


Emily September 27, 2008 at 3:30 pm

While I would never advocate being uncaring about our children’s reactions and feelings, I do think that this issue sometimes gets blown a bit out of proportion. Would you hesitate to take Benjamin camping with another mama friend, just because you weren’t sure when it might happen again? I haven’t yet jumped into the dating pool again, so maybe I shouldn’t be too hasty, but it seems that for young children, the only difference between a regular friend and a romantic friend is in our grown-up heads. (Assuming there is no PDA, etc.) I have friends over for dinner without any thought that my son might form a deep emotional bond, or worry about seeing them again. He learns that it is nice to have people come over. (We haven’t worked up to the toy sharing part of a playdate yet.) IMHO, if Benjamin sees you being social, talking to people and enjoying their company, then you are modeling something wonderful about human relationships. (And that they don’t steal your Thomas toys, as my son fears!)


Kat September 27, 2008 at 3:43 pm

It sounds like you’ve already decided that this relationship will never work/never be long term, so what’s the harm in a fun camping trip?
Bring the kids, sleep in the tent with your son, but it would be a fun camping trip amongst friends who have kids.
Your son would get some kids to play with and you’d have an adult to talk to.

I agree with you that trying to date someone who lives so far away and doesn’t own a car would be impossible to do, but why deprive yourself and your son of the fun of a camping trip with a friend?

Just go, have some fun, let your son have some fun, and just be friends.

Eventually there will be a man who lives closer, has a car, and will sweep you off your feet, but for now, just relax and have some fun.


Rebs September 27, 2008 at 4:38 pm

I’m with Emily…Go for it.

Trust your heart and your parenting intuition. It would do Ben no harm at all to enjoy a camping trip *and* get a chance to see you interacting with a man who is not a family member.

I leave you with this:

“…mothers and children benefit when the mother lives her life, and practices mothering, from a position of agency, authority, authenticity and autonomy”
–Andrea O’Reilly, Mother Outlaws –


Oakland Mama September 27, 2008 at 5:46 pm

I think you hit the nail on the head with your last statement:

“Do you feel like, in the name of protecting your children, you may actually be hurting them by denying yourself your own happiness?”

Your child needs you to model happiness, good relationships, balance. He needs you to do it in a sensitive, thoughtful way that takes into account his needs – not the rules. I mean, it’s not like you’re going to parade this guy in and out of your bedroom. It’s not as if you are going to tell your kid to start calling him “daddy.”

I often arrange joint family “play dates” with MY friends and their families. The kids play and hang out, the parents talk and hang out. This sort of adult interaction is NECESSARY to your sanity.

I say let this guy be a friend, get to know him, camp, talk, relax. If it’s meant to be, it’ll be. If it’s not, your son had some fun camping.


Patricia September 27, 2008 at 6:00 pm

You know how sometimes your around moms who are so overprotective over their children, that it strikes you as unhealthy?

I think that in that same sense, you may know people that leave comments, but you don’t really know what kind of parents they are. THis isn’t a jab at anyone who has commented, I think it’s just something you have to consider.

James met Isabella immediately, but, she was just three months old. If your head is clouded by all the opinions I don’t think you’re going to get full closure on this guy, and then the what-ifs start, and you start getting a little bitter at life because you feel like you’re not allowed to date or have fun with the rules in the way.

People that tried to put rules in my life weren’t always sincere. In fact, sometimes it was just shear jealousy. Not to toot my own horn, but there was no other reason for some of the advice I got from other single parents or people.

Our kids are resilient; more so than we give them credit for, in my opinion. If little Ben can handle his dad dating someone new, who also has a child, I think he’d be okay with you hanging out with a member of the opposite sex, who also happens to have children he can have fun with.

Good luck!


Amy Nathan September 27, 2008 at 6:48 pm

Kids ARE resilient – but why should they have to be if it’s not necessary? Your son doesn’t live with two parents, I don’t know how often he sees his dad or what it’s like when they’re together, but whomever said kids don’t know the difference (even at 2) between a friend and a “friend” they are wrong, imo. If you are going to casually date someone, with whom you see no future, find someone close to home for a movie and a quickie when your son is with a sitter. That won’t touch your little one.

It’s not overprotective to keep these parts of your life separate. In my humble opinion, it’s smart parenting.


jenn September 27, 2008 at 8:46 pm

I’ve always felt that you should keep your dating life separate from your children, but I haven’t started dating yet, so what do I know. I think it’s all about common sense. I don’t think someone should bring a boyfriend in and make him almost part of the family (there constantly, bonding with kid), unless it’s very serious. A camping trip in separate tents seems pretty harmless though, especially if it’s something you would do with another friend. I think the fact that you care enough to worry about it means that you’ll be careful and make the decision that’s best for you and your son.


Amy In Sedona September 27, 2008 at 9:21 pm

Im glad I made an impact! You can have seperate tents and it can be a fun adventure for Ben, dont deny yourself your curiosity… and thank you for being a great single mama role model : )


Taishi February 5, 2015 at 9:18 am

Downingtown Grandparents Weigel – Awww! These photos are the next best thing to being there!!!Thanks for canutripg the amazing faces of precious little Ben for us. We have looked at them 6 times in the last 5 minutes! Just can’t get enough of him!


Savored Life September 27, 2008 at 11:05 pm

Stop talking yourself OUT of everything! Go. Interact with Cabin Man like you would any other male friend in front of Benjamin. You are, in fact, building a friendship with him initially….

I have a single dad friend that I do things with all the time. We are actually going camping next month! There’s nothing romantic, the kids are great together.

You have to LIVE your life. Trust YOURSELF and your thoughts. You are a great mom and you deserve happiness, excitement and fun!

So…look forward to reading all about it!! 😉


Jowela February 4, 2015 at 2:44 am

Your article pecfertly shows what I needed to know, thanks!


Laura September 28, 2008 at 5:14 am

I wouldnt throw in the towel! Maybe re-evaluate your r/ship but dont throw in the towel! So it may be harder to get alone time but I still maintain you CAN do things with the kids! And you may end up awesome friends!

I dont introduce my kids to every Tom, Dick and Harry I date but those I know my kids and there are people I have introduced them too! People who have not remained in my life! Like I deal with the loss so do they!

I refuse to stop meeting and making friends with people in case my kids get hurt. Yes, like any parent, I protect them from blatant hurt but the life of a single parent is different! The rules are NOT defined. The lines keep moving. And I just go with what feels right for us!

I had a friend a few years ago. A single dad who had custody of this two girls. He met a women in America. He would fly to go see her and they had a r/ship for years. He proposed and the kids met her when she came over the wedding! Now, to me, that is not healthy!


Carrie September 28, 2008 at 8:25 am

This is a bit off topic, but how come a single father living in the woods and building his own house does not have a car? How does he get himself and his kids around? I can’t imagine there are many buses and taxis driving by.

Is that at all a red flag for you? It just seems a little strange.


jonb September 28, 2008 at 9:26 am

I think you are thinking realistically. The distance is s killer, and with children it does change the dynamic drastically.

I beoieve the rules, so to speak, are not written in stone. They serve as a general guideline(sort of like the bible) on how to manage yourself and your child. However, one cannot deal in absolutes all the time. You have to use your judgement of the situation at hand and its various components to make your decision.

The rules are based on the past and made to protect the future. But what matters is the moment you are in. That moment is dynamic and constantly changing. You have to adapt to it on the fly.

If in your shoes, I would think it would be alright to relish in the moment. It may not be meant to be long term wise, but for a few moments you may smile and laugh, and enjoy sharing time with someone who sparks your interest. You will learn and take something from this regardless of the outcome.

My suggestion: Get some other parents and kids to go, like 2-4 more groups. Find a camp site half way and do a communal social thing. The adults can interact, the kids can cause mayhem, and if nothing they will have a new group of friends. Once the kids are asleep you and Davy Crockett can steal away for a walk by moonlight to chat and feel a little romance.

Bonus* Choose a camp sight with a lake so you can talk while watching the moonlight reflect off the water. A bottle of chardonnay wouldn’t heart either. 🙂


singleworkingmommy September 28, 2008 at 11:45 am

I don’t know if this will help or hurt, but it’s a similiar situation in a way.

My Son attended daycare with a friend’s child. Son had to switch daycares, and I had a falling out with this friend. So we never see them anymore. He asks about his friend ALL the time (Nothing about her mom), and it breaks my heart when asks where she is.

They haven’t seen one another in at least four or five months, but he still asks about her once in awhile. He talks about her birthday party and he actually still signs “friend” when he says her name. He’s only 2, so I’m hoping he’ll forget soon.

Point? I’m not sure there is one. Son still asks for his friend, and Nina and Pop-pop (they don’t live around here), but does he ask about the guy he met at the mall? Or the male friend that came over once to help me move a couch? No.

I think there might be more thinking being going on because YOU feel for him more than the average joe or friend of yours. Just because you feel more, doesn’t mean Benjamin will. My advice: Do what you want, think less (hard, I know.)

Pfffttt… I’m not even sure what this post means.


Jay September 28, 2008 at 12:14 pm

I definitely agree with you about not showing too much to the kid too soon. I dated a woman that had a cute kid, but she introduced him too fast. I didn’t mind because he is great, but I almost felt like she was raising his hopes of a guy being around; and that can put burden on the guy to stick around a-la Jerry Maguire.


O Solo Mama September 28, 2008 at 1:47 pm

Alaina, the person who mentioned playdates was right on. Think of it as an extended or glorified playdate where the kids get to do their thing and the adults get to talk. Benjamin doesn’t know there’a a debate about any of this. He’ll just enjoy the experience as a great outing. This is if you want to go, of course. If you don’t, don’t bother second-guessing yourself–life’s too short!


mssinglemama September 28, 2008 at 2:01 pm

I LOVE this conversation and these comments.

I’m rushing off to the park with Benjamin, his best friend Sydney and Mattias, the son of a single father who has been in our lives for one year now. Kind of fitting for this discussion…

Anyway, not much time, but to answer the car question:

He sold his car when he quit his traveling job to be near his kids. He definitely isn’t swimming in cash as he’s re-building his life after his divorce. His cabin is actually just 100 feet away from his parents house, so he uses their car to get the kids, etc. But taking their car for 48 hours to come see me would be difficult…

Believe me, I could car less about his car situation – I was in the same situation myself just one year ago. I had a car, but I had lost everything else – so…

The reason he doesn’t have a car is kind of a turn-on actually. I admire people with strength who throw away materialistic definitions in the name of being with their kids and getting their life together.


J-Fo September 28, 2008 at 6:46 pm

My advice is to try and not get too mired down by alllll of the advice! Honestly, from everything I can tell so far, you are a brilliant woman, outstanding mom, and place an extreme priority on your son. If your gut says that you can do the camping trip and do it in a way that seems like a fun friends outing…do it, do it, do it!!

I don’t agree that two people that are interested in one another “can’t” hide this from the younger kids. C’monnn.

I speak as someone in a rather interesting, impractical, completely unexpected “new friend” situation myself (oh, and I have YOU to thank for this, but this is a tale for offline!)…so perhaps my thoughts are a bit biased.

But, honestly? You know you and you know Benjamin better than anyone else. Don’t miss out on great if you can find a way to explore it in a way you’re comfortable with.

And remember that, if the advice starts bugging you…stop asking for a little while and do your own thing! 🙂 (Like we all know what the hell we’re talking about anyways!!)


PT-LawMom September 28, 2008 at 7:41 pm

I think that your happiness will ultimately make your son happy. But then again I’m a go-with-your-gut kind of girl. Not sure how that will work in terms of dragging my kid along for the ride, but it always worked out well pre-kid. Good luck!!! 🙂


Anonymous September 29, 2008 at 6:57 am

I’ve thought a lot about this situation the last couple days & I’ve been swayed to “go for it”. I know there are probably many opportunities I’ve missed out on for the sake of my kid that have done more harm than good. Had I taken the risk now and again, I might not still be single & we’d have a great person in our lives.

I’m just saying, getting together with the kids could be a good thing as some have suggested. If he isn’t “the one”, you’ll always have a camping buddy and Benjamin will have some really fun trips. You’ll never know until you give it a fair shot.

Life’s feeling too short today, live it while it’s there 🙂


Leslie September 29, 2008 at 6:58 am

lol life’s also too short to add my name haha me above.


Andrea September 29, 2008 at 6:27 pm

A couple of anecdotes–take them for what they’re worth.

My ex rushed the introduction with his new g/f and her son, and it backfired. Not in an obvious way, i.e. Frances was only upset with ME, but it was obviously connected with him (and I didn’t know how quickly they’d all been introduced or how much time they spent together until a few weeks afterwards). Kids know. Kids know when a friend is special and it makes them worry about what thsi special friend means for their own future–for how much attention and time they’ll get from their parents and whether this person will stick around etc. I’ve talked to adult children of divorce adn they say the same thing. They won’t necessarily show you when they’re upset because they don’t want to upset you; that doesn’t mean it isn’t bothering them. KWIM?

I worried a lot about this with my current boyfriend, even after having dated for several months and seeing it move in a serious direction I worried about the impact on Frances were we to break up. So my compromise was to talk to the boyfriend about that eventuality, to see how he felt about remaining friends with Frances if that were to happen, and he was fine with that. That was reassuring b/c I could have some faith that even if the boyfriend were no longer my special friend, he and Frances could still be buddies and Frances wouldn’t lose him, which was my biggest concern–that they would get attached and we would break up and she would think he was leaving HER. (Even so, seven months of dating and she’s seen him 3 times. I won’t personally feel comfortable spending lots of time with all of us together until we are making plans to move in together. That’s just me.)

is that something you could try with cabin man? The “what happens if our kids all get attached and we break up” talk?


Rita February 3, 2015 at 7:07 am

Why does this have to be the ONLY reillbae source? Oh well, gj!


Renee September 30, 2008 at 10:17 am

You are an amazingly intelligent woman; that’s easy to see in just a few blog posts. You know yourself better than anyone else. You also know your kid better than anyone else. This is an area where advice is great as long as you don’t actually take it. 🙂 But I know… you posted the request so you could get some thought-provoking ideas. Here’s my contribution… 🙂

Just give yourself a deep double-check to make sure you’re not thinking your own comfort zone and your kid’s comfort zone are exactly the same (we tend to do that a lot as parents, I think… assuming our kids are more like us than they really are… not meditating on exactly who they are enough sometimes and how they are different).

Then give yourself a deep double-check to see if you are repeating any mistakes from the past. Do you have a history (pre-child) of getting swept away and getting in a little too deep, too fast? If you don’t, then good. I know I tend to have more lenient boundaries early in relationships because my absolute favorite part of a relationship is the point where we get really comfortable with each other and can just relax around each other. I want to get to that blissful point so much that I move faster than I should sometimes. It did get me hurt occasionally in the past, but even so, it had much lighter implications for me back then than it would now that I’m a single mom. So I work hard to force myself to put on the brakes a little more than I *want* to. In other words, in that one particular department, I do force myself to temper my gut feelings because I know I need to. That’s an aspect of my personality that’s been hard to change.

If you do those error checks beforehand and are totally and completely honest with yourself while doing them, then your own advice will be the best advice you can get.

My one other rule with myself is to never, ever get serious with anyone or allow them to be around my kid alone without doing a background check. Might sound a bit harsh, but I’ve learned a lot about sociopaths (unfortunately), both vicariously through friends and through firsthand experience. I know that because of the way their minds work, my intuition — as honed and sensitive as it is — is not totally reliable in picking out a sociopath. My budget has a line item for background checks. That’s how serious I am about that.


April October 1, 2008 at 1:50 pm

I haven’t read all the comments, but here’s a thought: why doesn’t Cabin Man talk to his ex about maybe changing the agreement a little? It doesn’t seem right that he has no weekends free whatsoever.


Patricia October 1, 2008 at 5:23 pm

I just have something along the same lines of the car.

When I was waiting tables after I had Izzy, a guy was hitting on me and said me not having a cell phone was “vintage” and attractive.

I mean, I know it was a load of crap, but if I met a guy w.out a cell phone, it probably would peak my interest.

Vintage…it still makes me laugh.

I have a cell phone now.


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