The Single Mom Dating Conundrum.

by mssinglemama on November 11, 2007

It’s been four weeks now.

My new relationship status is beginning to sink in.

I have a boyfriend, and I’m actually enjoying it immensely. Usually at this point fear takes over and I start pushing them away. I slowly eject them from my life, or cut it clean depending on my mood. But this time, I’m not feeling that way. I’m not stressed at all. I’m completely comfortable with him and totally into him. So far, the feeling is mutual.

I had him over for dinner on Thursday night. Benjamin was still awake. Kris has seen Benjamin in the mornings briefly but this would be his first evening with us, usually the highlight of my day because Benjamin is chipper, happy and ready to play.

Kris walks in, gives me a hug and then crouches down on his knees, “And, how are you?” He looks at Benjamin and Benjmain stares back. This is odd, usually he flashes a smile and runs away but he can’t take his eyes off of Kris.

Kris leads him into the living room and opens his toy chest. This is a first. Of all of the men I’ve dated since the divorce not one has genuinely just sat down and played with my kid. This used to surprise me because I thought – “If they’re trying to win me over wouldn’t they want to at least try to play with him?” To their credit, some would try, but it was awkward and forced. “I’ve never been around kids,” they would say. “I don’t know what to do.” Kris has never been around kids either, he’s actually only 23. Five years younger than me.

While I’m in the kitchen cooking dinner, I hear Kris talking to Benjamin, he’s calm, assuring and playful. A few hours later I take Benjamin up for bedtime. I come downstairs and all of his toys are cleaned up. Kris had tidied up my living room. I’m now pinching myself.

Kris is still there in the morning. We all eat pancakes together. There’s lots of laughter, more playing and the entire time Benjamin is following Kris around like a little puppy. I put Benjamin down for his nap and say good bye to Kris, we both have to work.

When Benjamin wakes up four hours later (he has a nasty cold which is why I’m home on a Friday) he searches the house for Kris. He’s going from room to room. As soon as he realizes Kris is gone – he starts crying…hard. My heart breaks. What am I doing? What if this doesn’t work out? Where will we be then? Benjamin is clearly well into toddlerhood (20 months) and now he is very well aware of what’s up.

The single mom dating conundrum:

When a man enters our life we want to see how they would fit into our family, or if they can even handle it. But we can’t do it without introducing them to the kids.

The solution:

When Benjamin was a teeny tiny baby, this wasn’t an issue. So everything I’m about to say clearly depends on the age of the children.

I’m not big on the idea of waiting six months to bring a man into my daily routine. I guess it’s because I’m afraid he would be shocked at the reality of how hard it is to raise a toddler and then split. Then I would have invested six months of my time in a guy who wasn’t really there for the right reasons.

The other problem. I am a working single mother. Not bringing him around Benjamin leaves me only a few hours in the late evening. Period. This can get old and can also hurt a budding relationship.

I have learned from my past mishaps not to raise this issue too early. Why? Because there is no way he or you actually know how long this will last yet, and you shouldn’t presume to know that. Once I actually told a guy I was dating, “the only way I can date you is if there’s potential – potential that one day we might get married.” We had only been dating for a few months. I didn’t even want to marry him. Isn’t that crazy? I just had to rationalize why I was spending time away from my son – to myself. In the end that one just fizzled out but the moral of the story is – it could have been more fun if I would have left my drama in my head. I’m thinking this is probably a good conversation to have 6-8 months in to a relationship. Just a hunch, but to each his own.

My solution: I am going to keep Kris’ encounters with Benjamin to a minimum for the next few months, but he will have a few. Because I also want someone to fall in love with my son, not just me…we are a package deal.

Related posts:

  1. Single Mom Dating Tips, Part 1
  2. E-harmony Dating Review: for the single parent or any other dater
  3. Online Dating: Rules of Thumb
  4. MySpace, Facebook and Dating in a Virtual World.
  5. Online Dating Etiquette: How to break up…virtually.

{ 5 trackbacks }

Is marriage out of style? « Ms. Single Mama
January 14, 2008 at 12:02 am
Telling the kids…Single Mom S.O.S. « Ms. Single Mama
January 23, 2008 at 2:26 am
One Step Back. « Ms. Single Mama
February 7, 2008 at 12:24 am
Getting over it. « Ms. Single Mama
February 12, 2008 at 5:40 pm
Need a man? Look in mommy’s bed. « Ms. Single Mama
March 30, 2008 at 1:32 am

{ 10 comments… read them below or add one }

Morgan November 11, 2007 at 6:12 am

I can relate completely (the beauty of single-momma-sisterhood!).
The first boyfriend I had after my son was born lasted 6 months (from the time my son was just a little bug, 4 months, to the time he was just about taking his first steps, 10 months). I remember praying “God just give me a man who can fall in love with my son!”
Well, what they say is true: you get what you ask for, so you better be careful in the asking!
My boyfriend DID fall in love with my little guy but he really didn’t fall in love with me.
In just 6 months of dating we became a boring and sad old married couple that really had no relationship except for talking about their kids.
I learned my lesson. Its important the boyfriend IS good daddy-material, but first you better find out if he can be good to you!


Corey February 7, 2008 at 7:11 pm

Thanks for pointing me to this. I had to keep my boyfriend from my daughter due to custody/divorce issues for almost a year. Once he did get to meet her, he was afraid (as was I!) but has completely fallen in love with her. He does a lot of things with us, but doesn’t spend the night (because I don’t want my daughter to completely feel like he *is* a part of our family). We’re still working things out and our relationship may never progress from the point it’s at now. But for now, that’s ok.


Katy Mendoza November 12, 2008 at 7:01 pm



Clarissa March 27, 2009 at 4:57 pm

Hi, I'm a single mother of two little men, ages four and five. I've been seeing someone for over a year now, and I love and appreciate every, single aspect of him except for his view on what he feels his role should be in my boys lives. He doesn't feel as if it's his responsibility to ever try to create any kind of emotional connection with them. He said that he just feels as if that's my job seeing as they're not his own, and that if we ever decide to tie the knot in the future, as long as he's taking care of them financially and teaching them the life skills they'll need to be good men, not truly "loving" them won't have an impact on what type of people they'll grow up to be…what kind of crap is that?! The whole situation really upsets me every time I think about it because everything else about him is literally everything I've ever dreamed about finding in someone. If he loves me, he should learn or at least attempt to love my children just as much, if not more, right? Am I wrong to feel this way?


Heaven July 22, 2011 at 11:43 am

YES he should tryto love your children, my aunt is in a similar situation he and her boyfriend of ten yrs now, when they first meet they both had one child and she treated and loved his child like she did her own but he wasnt there emotionally for hers she acted as if this was normal and now they have a child together. The problem is that his son and the son they had together both thrive emotional and socially like a child should but her son doesnt do so well emotionally with men and will openly admit he doesnt like his moms boyfriend because he doesnt treat him the same.


Ivonne February 5, 2015 at 9:36 am

flutterby, whatever you need to do to jfstiuy it. Every writer is different. I just make a general long-term survival suggestion here to not do as you suggested and write more. But every writer is different. Read Kris’s article, folks, about scale and thinking small.As of today WMG Publishing Inc has 280 titles. We sell thousands of copies per month and that’s growing quickly. I would have to hire a full-time employee to do as some of you suggest and check numbers for that level of titles every day. And when we get to 1,000 titles and Fiction River and other anthology series are running at full speed, it would take two employees to do it every day.When looked at in that fashion, you can start seeing how really silly it is for any reason.


susan July 26, 2011 at 12:04 am

Yep I reckon it’s a package deal. I know this is an old post, and so interesting considering where you are now, but I’ve been reflecting on this very issue.
What if you wait 6 months and then the kids and him can’t stand each other? what if you introduce them too early and it wrecks the relationship? what if the person is slowly introduced, the kids love him, and it turns out you don’t?
Seems to me it’s almost a no win. that said, I am OVER hearing people say to me óh if I were in your situation I’d just accept that I have to be single until my children leave home’(ffs, they are only 5 and 8….that’s a long time between drinks!)


Angel November 3, 2012 at 8:29 pm

Hi love your site. I have been battling dating and I met someone but he disappeared after we slept together, that was 2 months ago and I was a wreck, my daughter and my career felt the brunt of the hurt. I am just trying this again and with online dating find it hard to decide if I should be posting fact I have 1 child living at home. I am scared of predators of children then secondly guys looking to score since lots of guys only wan to hook up with single moms. Can you tell me if I should post fact I have a little girl, I am so scared that I just want to put I don’t have a child in my profile date and then after I like a guy tell him the truth. But. Don’t want to lie either.


Cleveland February 10, 2014 at 6:03 am

The water of the relationship gets hotter and
hotter but you are getting used to it ”. Keep updating your blog by
adding content on a regular basis.


lee March 1, 2015 at 11:15 pm

Well, the reasons you mentioned are exactly the reasons I didn’t date when my son was still home with me.

1. I worked all day. A long day. He was with sitters or in a before & after school program or a summer camp for 10 hours a day. Was I supposed to leave him with another babysitter for even longer to — what, go sit in a bar with some stranger?

No, my son was more important, and he needed me more than I needed some guy.

2. My son lost his father. He loved his father, then his father was gone. He was heartbroken. Dating, by it’s very nature, is experimentation. Kids don’t understand that. Kids LOVE. Full-out, whole-heartedly LOVE.

Unless I was extremely lucky and it happened that the very first guy I would date would become THE ONE, — if I let the guy meet my son, I’d have been setting my son up for a heartbreak. Again

No, I was not going to do that to him.

3. I was just plain tired.

4. My circumstance was probably a little different than most. My husband died, so he was not going to be picking up my child for sleepovers twice a month. My family is a thousand miles away, so there were no weekends at Gramma’s. There was only me. What a supreme rip-off for my son, to have just one person in the whole world for his family.

I wasn’t going to take even a little part of that away from him.

I came to the conclusion that there was no room in this single mother’s life for dating.

So now my son is grown and gone. Yes, I’m lonely. Yep, I saw it coming years and years ago.

Still, I wouldn’t change a thing.


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