You Got This, Girl! 10 Single Mom Dating Tips

single mom dating tips

By Jackie Pilossoph, Founder, Divorced Girl Smiling, the place to find trusted, vetted divorce professionals, a podcast, website and mobile app.

Jackie, I’m wondering if you can write about dating as a single mom when your ex is especially difficult.  In any divorce, when you think about dating again, you get overwhelmed, but what if you add to that worries about your ex actually trying to sabotage any attempt to move on, just to “get even.” I could really use some single mom dating tips.

Here you go!!

10 Single Mom Dating Tips

1. Make sure the guy knows you are a single mom. In other words, don’t try to keep it a secret.

A friend of mine met a woman he fell head over heels for. It always bothered me that she didn’t tell him she had two young kids until the 3rd or 4th date. Why was she trying to hide her children instead of taking pride in her two most beloved human beings? That really showed her insecurity in my opinion.


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Was she insecure and afraid he wouldn’t want to go out with her? In other words, she felt she had to sell herself and then “break it to him” that she had kids. That disappointed me. The girl turned out to be a complete nightmare, liar and cheater, and it didn’t work out, anyhow. But, my friend did not care AT ALL that she had kids. In fact, he liked it.

2. Single mom attire and dating attire are totally different.

If you feel like saying, “Jackie, please don’t insult us, we know how to dress for a date,” then I apologize.But, true story. A single mom I know came to a party I was at dressed in yoga pants and a t-shirt, her hair in a ponytail and no makeup. Now, there is nothing wrong with t-shirts, in fact, I love t-shirts and yoga pants and ponytails, but there is a time and place to wear them!

And, this is a woman who really wants to meet someone. In other words, she wasn’t just there to see her girlfriends. When getting ready for a date, keep in mind that even though you are a great mom, tonight you are an attractive, feminine, sexy woman, and your goal is to feel as pretty as you can.

 3. Know when to stop talking about your kids.

I could go on and on about what a great kid my son is, or how cute my daughter’s smile is, and think nothing of it. But know when enough is enough. A date is about getting to know each other, so try to focus on asking the guy questions about himself and his life and sharing information about yourself.


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I do get it that kids are a huge part of a single mom’s life, but just remember that there’s a lot more to you than being a mom. Where did you go to college? What do you love about your career, or where you work? What are your dreams? What’s your favorite ice-cream flavor? What do you want in your life at 40, or 50 or 60?

4. Be honest and upfront about why you got divorced.

Don’t take this the wrong way, but you need to have “a story.” Not a made up story, just a good answer for the question your date will surely ask: “Why did you get divorced?” A bad answer is, “Because my ex is a total asshole.” Just be honest, but leave out details that will make you seem angry or bitter, or that you have the victim mentality.


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 5. Don’t badmouth your ex or talk about things he did or is doing that bug you.

That will turn off your date and you will most likely never hear from him again. If you want to complain about your ex, call your girlfriends, tell your therapist or journal your feelings.

 6. Don’t introduce him to your kids too soon.

Just because you are head over heels with your new guy, doesn’t mean your kids are going to be. This is where not being selfish has to come into play. Enjoy the new relationship for yourself and give your kids a break. They will meet him eventually, if you end up getting serious. Your kids will have such a better reaction if you wait a little while.

 7. Have faith in your new guy, regardless of what he might be hearing around town or from your ex.


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When I hear a guy bitching about his ex-wife, I kind of roll my eyes, and chances are, that’s exactly what your guy will probably do, should your ex try to “warn” him of getting involved with you. It’s totally out of your control. It’s your word against your ex’s. So, if your guy really loves you, he is going to take your side and decide for himself about you and your character. Have faith!


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 8. Don’t constantly talk about how hard it is being a single mom.

It is hard. I know that. And, chances are, if your date is a single dad, he knows that, too. So, no need to talk about how you were carpooling all night, or that you are working two jobs, or that your ex rarely sees the kids. Single moms are rarely validated. So, don’t expect to hear how great you are from anyone.Know in your heart how great you are. That should be enough.

 9. Take it slow.

If your date thinks you are interviewing him for husband number two, he is going to run away really fast.

 10. Enjoy yourself.

Dating is supposed to be fun, so don’t put pressure on yourself that it has to work out. Every date, every guy you meet will add something to your life, hopefully something good, whether it works out or not. So, just go in with that attitude and you can’t lose!

Like this article? Check out, “9 Signs of a Healthy Romantic Relationship”

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    Jackie Pilossoph

    Editor-in-chief: Jackie Pilossoph

    Jackie Pilossoph is the Founder of Divorced Girl Smiling, the media company that connects people facing with divorce to trusted, vetted divorce professionals. Pilossoph is a former NBC affiliate television journalist and Chicago Tribune/Pioneer Press features reporter. Her syndicated column, Love Essentially was published in the Chicago Tribune/Pioneer Press and Tribune owned publications for 7 1/2 years. Pilossoph holds a Masters degree in journalism from Boston University. Learn more at:

    4 Responses to “You Got This, Girl! 10 Single Mom Dating Tips”

    1. Gina

      These are great! I struggled with #6…I think it really depends on the situation. My (ex) boyfriend didn’t meet my boys until we had been exclusive for almost 3 months. I have other friends who didn’t introduce their new boyfriend for almost a year. I think it just depends on your relationship, your children, etc.

      Good advice as usual, Jackie!

    2. Byron

      Aghhhh! You ladies have too many rules! We guys are way less complicated than you think we are.

      My number one rule: “Be yourself” Don’t set yourself up to be discovered as someone other than who he thought you were.

      I have to laugh a little, but the whole “dating attire” thing. Situationally dependent. If you’re spending extra time and effort because YOU want to, that’s one thing. Think of the endstate though – if you meet someone and it progresses, he’s eventually going to see you without makeup and maybe in some baggy college hoodie and sweatpants. Let’s put it into a different context. He puts a party on at his house, he’s nice, doesn’t mind that you have kids at home, has a nice house, nice car, looks like he’s secure? But, six months later, you find out that he’s actually been house-sitting for his uncle because he can’t hold a job. Now what? He’s nice, but…what are you going to say when he calls you next?

      My last “first date” was a hike. Imagine my surprise when we had theater tickets weeks later and the frumpy, sweaty, dusty, plain girl I’d had so much fun hiking with turned out to be a rockstar when she dressed for the occasion?

      Be yourself. There really are only three things I know of that most of us guys will consider dealbreakers: Self-absorption, Anger/bitterness; and Desperation. If we sense that you’re any of those, you’re probably not going to get a second date. It works the other way, too. The guys you want to avoid will see your kids as competition or are Angry/Bitter or Desperate themselves. We can only change ourselves. Most of us don’t need to change as much as we might think we do.

      One last, regarding kids. Hers were in college, mine were still in junior high. I met hers fairly soon, we waited almost a year with mine. And from my own experience, I think I’d suggest that the younger your kids are, the longer you should wait to introduce them? As time goes on though, even younger kids are going to wonder who you’re spending your non-parent time with. Let them become familiar with a name, gradually talk about some of the fun you have together. Kids have a remarkable sense of when you’re happy and will trust it if you don’t drown them in it – don’t give them too much to absorb at one time. They’re still kids, not BFFs. “I didn’t know this person yesterday and today we’re at Disney World” is not a good thing. My kids’ mom has introduced them to her “friends” too early, and it seems like it’s then just a matter of days before things are over with, which is kind of sad.

    3. Trevor

      2) “A single mom I know came to a party I was at dressed in yoga pants and a t-shirt, her hair in a ponytail and no makeup.”
      —So what? If you show up to a party as yourself maybe you’ll find someone who appreciates you for who you are. Nothing more sad than single moms acting like they’re in the late teens/early twenties. Which is the norm I’ve found with single moms I’ve met out. No offense. Word of advice ladies. Don’t listen to #2. If you want to meet someone who appreciates you for you than be yourself. Dressing up nice and putting on makeup is just a mask that hides your true self.


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