Tips for dating a single mom (12 things NOT to say)

I go out with single dads and childless men alike, and some of the latter admit (while others appear) to be uncertain about the logistics of dating a single mom.

On one hand, Dude, we are just like other women! Proceed as normal! 

On the other, our lives are likely both wonderful and challenging in ways that childless women's are not.

If you landed here, you are likely a guy (or woman) who is attracted to single moms because:

  • You're a single parent, too, so you want to connect with someone who understands your jam (single moms want to date single dads, too, btw)
  • You don't have kids, and feel too old to be a dad to a newborn (and are keeping it real about the realities of babymaking with a much, much younger woman), but would like to be a father — in this case, a stepfather to older kids
  • You just tend to be attracted to moms, and you can't figure out why.
  • You have feels for a single mom in particular, and you are unsure on how to move forward.

If you are someone interested in dating a single mom, take 5 min and read 9 reasons dating as a single mom is so much better and understand why it will be worth the extra time and effort you may have to put in!

How to date a single mom

Helpful tips on how to connect, the logistics, meeting her kids ….

Ask her out ASAP — single moms are busy!

Leave the ask to the last minute, she has to scramble to find a sitter and that's really uncool.

Plus, it tells her (and any other woman, for that matter) that she was your Plan B for the evening.

Which she may be. But if you really want to see her and invest time in getting to know her, give the woman plenty of time to sort out her schedule.

If she wants to date you, she will find a way to make it work.

Ask about her kids

She won't assume you're a pedophile.

This shows interest in one of the most important things in her life.

In fact, if you DON'T appear interested in her family she'll think that you're not into kids.

Let her know you love kids — especially if you're a childless man

Assuming it's true.

Sounds cliche', but I always appreciate it when a guy goes on about how much he adores his niece or spends time with a friend's baby.

When a guy laughs at my funny-kid story, or is sympathetic about my mom worries, I'm in.

Don't assume she is broke just because she's a single mom

Maybe she is broke, but don't assume.

Don't assume single moms' kids need a new dad

They have a dad, or they don't.

You are not being interviewed to be a parent — you are being interviewed for your potential to be a romantic partner.

Of course, that could involve — way, way down the road — being a part of a family with children.

These things are complicated, I know.

Bear with us. But just follow her lead here.

If you're out and she is paying for a sitter it is really nice if you get the check

This isn't necessary, and especially after you have been involved for a while you will likely sort out the who-pays-when conundrum.

But if you tend to take turns picking up the bill, but she sometimes rearranges her life to get out of the house and pays for a babysitter so she can spend time with you, acknowledge that.

Hang tight on asking about visitation schedules

Of course, you want to know when she is free, if she has the kids all the time and whether the dad is involved.

But if you explicitly ask for these details on the first or second date you will appear reluctant about dating a woman with kids.

Which you may be – but if you ask too fast, she will know.

But she wants to feel like you're interested in her in every part of her womanhood — including motherhood.

Don't assume she's not free when her kids are home

Women like to be asked out. If you're interested and want to see her, ask her out.

If she prefers not to go out when her kids are home or doesn't like to hire a babysitter on school nights, she'll tell you. Because she may be dying for a good reason to hire a sitter, or take her brother up on his offer to watch the kids or otherwise go out and spend time with you.

If you don't ask her out — no matter how innocuous or considerate the reason — she will assume you don't want to see her.

Wait for her to bring up introducing the kids

If it has been more than a few months, or things get very serious very quickly, and she hasn't brought up introducing the kids, bring it up.

Know that when she invites you over, it is more work for her than when you invite her over

Yes, moms are really efficient and they're used to doing a lot of cooking and cleaning.

But if a single mom invites you over for dinner — whether a romantic evening for two, or with her kids — she had to clean up a whole lot of Legos and finger paint and string cheese wrappers and wrangles in an extra trip to the market and wine store to make it happen.

It may appear effortless, but effortless actually takes more effort.

Respect that it's a big deal when she introduces you to her kids

She is opening up her life and her whole family's life to you.

Treat this gesture accordingly.

Related posts on dating as a single mom:

Dating as a single mom is the same as dating as a teenager

9 reasons dating as a single mom is so much better

12 Things never to say to a single mom on a first date

We all say dumb stuff on dates.

Especially first dates when everyone is self-conscious and sussing out someone new.

But there are some things that you just do not say to a single mom on a first date, assuming you’re angling for a second.

Here are 12:

  1. “You look great for a mom.” That. Never say that.
  2. Don't ask to come over when her kid are asleep. Just don't.
  3. “That’s great your mom lives in town so you can leave your kids with her on weekends.”
  4. “I am really loving this time of my life since my kids went away to college.”
  5. “Wow, you look good considering you had two kids.”
  6. “Kids need a man in the house.”
  7. “You had a C-section? That’s awesome.”
  8. “You don’t even have stretch marks!”
  9. Your ex-husband lives in the neighborhood? Is his place near here [looking over both shoulders]? Do you ever run into him? Does he hate that you date? Has he ever beat up your boyfriends? Have your kids met any men you’ve dated? How did they react? Did they resent him?
  10. “Did you get your tubes tied?”
  11. “How much child support do you get?”
  12. “When guys marry single moms and their daughters grow into teenagers, I don’t know how they can control themselves.”
  13. “My ex has a lot of issues so I really want to get married so my daughter has a new mom.”
  14. “Do you masturbate while your kids are home?”
  15. “Not a lot of guys are interested in women with kids, you know.”

Interested in getting to know someone on a second date?

Commit this list to memory and never ever utter a single one of them.

Thinking of dating again as a single mom, but not sure where to start?

Dating sites used by single moms and dads

Check out a dating app. This is the easiest, cheapest way to get your mojo back, and get a feel for what is happening out there. All you need to do is connect with one cute guy to get that spark going again.

Online dating is one of the best things in the world for single parents — time and money efficient, and you can even do a background check a woman before you go out with her!

Here is my list of the best dating sites and apps for single moms.

EliteSingles is especially geared towards people who are educated professionals, looking for serious relationships.

  • 82% college educated
  • 100% verified
  • 90% aged 30+

Matchmaker sites for single parents

There is a reason matchmakers have been in use since the dawn of human sexuality — they work!

Matchmakers tend to be very expensive, with no guarantees. It's Just Lunch is different.

I did a lot of research on It's Just Lunch, and went through the onboarding process, which you can listen to in audio, and read the transcript. I am so impressed — if I weren't in a serious relationship, I'd 100% use this service.

Here is a deep review of It's Just Lunch, which is the largest matchmaking service in the world, and searches its network of literally millions of singles to find you quality dates. Here is what I like about it:

  • It's Just Lunch is 28 years old, reports 3 million first dates (!) and thousands of relationships and marriages
  • Guaranteed number of dates. They quote you a custom price that includes a fixed number of dates over a certain period of time (you can pause your engagement with penalty for any reason — including finding love 😍)
  • Each package 2 free one-on-one personal dating coaching sessions
  • Daters tend to be in their 40s and older, so lots of successful men who have kids and are open to moms with kids and successful careers
  • You are assigned a designated matchmaker who goes through rigorous training, and has years of experience — so their intuition is high!
  • Both parties pay and invest in the service — so everyone is equally invested in finding a quality relationship (and can afford the service)

In this post I lay out the pros and cons of matchmaking experiences, and you can hear for yourself as I go through what you can expect in your first experience with an It's Just Lunch dating specialist.

Video dating course — for single moms

Do you know a mom who is tempted to date — but stuck in celibacy? Is she unsure of how dating works in 2019 — with apps, texting, sexting, dick pics?

Worried about flaunting her new mom bod on the market?

That is why I developed the bestselling video course, Get Back Into Dating AGAIN for Single Moms.

This video course takes her step-by-step to work through your fears, hopes, create a dating site and get her sexy on.

Guaranteed to get the client on one quality, positive date!

Ready to try online dating? Read why you should try Elite Singles dating

About Emma Johnson

Emma Johnson is a veteran money journalist, noted blogger, bestselling author and an host of the award-winning podcast, Like a Mother with Emma Johnson. A former Associated Press Financial Wire reporter and MSN Money columnist, Emma has written for the New York Times, Wall Street Journal, Forbes, Glamour, Oprah.com, U.S. News, Parenting, USA Today and others. Her #1 bestseller, The Kickass Single Mom (Penguin), was named to the New York Post's ‘Must Read” list.Emma regularly comments on issues of modern families, gender equality, divorce, sex and motherhood for outlets like CNN, Headline News, New York Times, Wall Street Journal, Fox & Friends, CNBC, NPR, TIME, MONEY, O, The Oprah Magazine and The Doctors. She was named Parents magazine’s “Best of the Web,” “Top 15 Personal Finance Podcasts” by U.S. News, and a “Most Eligible New Yorker” by New York Observer.A popular speaker, Emma presented at the United Nations Summit for Gender Equality. Read more about Emma here.

20 Comments

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  2. kas on June 17, 2018 at 11:15 pm

    I am a single mom of 3 and I have been dating a man for almost 6 years now who also has children around my kid’s ages. He never invites me to his family gatherings or his kids sporting events. I made a big deal of always asking him to come to my kids events as well as family events. He rarely did and then just stopped so I quit asking. I have brought this to his attention how it makes me feel that he never invites me or even me and my children to his family events. I barely know his family and my kids have only ever meant his parents and his sibling because his sibling resides with him. It took me many times of bringing up the fact that he never invites me or my kids and its weird. we have been together for 6 years and I barely know your family. Cousins have gotten married and kids have been born and I have never meant them or the spouses. So he recently started inviting me and yes I mean only me. It seems he waits for when I don’t have my kids and it’s still only hear and there. Well lets just say being there is very awkward half the time no one speaks to me and the only ones that do are his aunts and uncles or his parents or grandparents his cousins who are around are age do not speak to me, unless I try to start a conversation. I truly feel they see me as this snob of a person who choses not to come around even though that is not the case I have just never been invited. And he does every holiday at his families house. Mothers day he spent the night before but left early because they were having family get together as they do every holiday. Why can’t he spend a holiday with us we never get to spend one together. The opportunity for me and my kids to move has come along and he wants us to move in, but how is that going to work. I can be very stubborn and I am not going to have us split every holiday apart doing our own thing. HIs cousins baby shower over a year ago I guess I was invited but he never told me till the day of it. I couldn’t go. Then that same cousins baby one year birthday party he tells me oh your invited too but I would have to check and see if ok for you to take your kids since its our weekend to have them…UMMM six years shouldn’t it just be a given? I am overly frustrated and even though I love the man, I am tired of dealing with the same issues over and over again, and now its to the point I don’t want to go to any of his family functions as I feel they now look at me a certain way and probably blame me for never coming around. I know nothing about them. And if my kids can’t go i’m not going. Or am I just being stubborn? Our relationship has been very slowwwwww. Over a year before meant each others kids, he hardly ever comes to me and I always go to him. We never go out. No date nights if he does ask me to go out or plan something fun he always cancels last minute and its usually when I look at the clock and say shouldn’t we be getting around and his response is “oh I don’t feel like going to tired” like seriously!!!!! what do I do to get my point across!

    • Val on July 11, 2018 at 6:08 pm

      You are only a convenience for him. He doesn’t value you. Move on to someone who treats you like a queen.

  3. Lovelifenhappyness on May 4, 2018 at 11:49 pm

    Her having children was not a problem for me at first. It’s what came after that broke my heart. Nothing I could do to save her. I lost trust in her. I can’t even comprehend the sorrow I feel. Any advice?

  4. Lovelifenhappyness on May 4, 2018 at 11:36 pm

    I met the love of my life. Found out the hard way she had a very bad substance abuse problem. She is also a mother of four children. Good news she is getting her life together and maybe also her children. Bad news is she left after all I went through.

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  6. Josh H on June 23, 2017 at 12:02 am

    This list very helpful. One thing though; as the son of a once single mother, I find it very important if you’re going to be in it for the long run to meet the children sooner rather than later. My mother saw it as ” if you’re going to be for me then you’re going to be for my children.” She made the man my sisters and I now call dad take us all out after many months of him asking her out. I believe it is important to meet the children and interact with them, they have serious persuasive power when it comes to you being able to continue a relationship with their mom
    After months of texting, snapchatting, & video chatting I recently went on my first lunch date with a single mother of two children who I’ve been into since highschool (I’m 22, she’s 23) & instead of having her stress to find a sitter I told her it would be fine for her to bring the children as long she was okay with it. Which she was, she later told me the children couldn’t stop talking about lunch & how nice & funny I was. She also said it was the nicest outing she’s had with anyone in a long time & that she was impressed that I was the one who brought up bringing the kids & that I actually interacted with the children. She has told me that she’s has been asked out a few times & once she brings up that she has children the men practically clam up on the spot & don’t talk with her again.
    I know that this isn’t always the case & will certainly not be the best choice of action for every mom. I’m not advocating for you to put your children out there like that because there is alot of creeps. Just in my personal cases it has worked out & could possibly for someone in the future.
    Also happy to say her, her children, & I will be going for another lunch outing tomorrow afternoon.
    Sorry for the long windedness. Just having the possible potential to step up like my dad did makes me happy. I know if something really becomes of this then it won’t be easy for any of us.

  7. Charlie on March 19, 2016 at 5:41 pm

    Hey Single Moms,

    I am in a situation which is why I am going to write a lengthy post. I think I am in love.

    I work in a big retail corporation. I met her at regional market training. She happens to be a manager at a store in the town where I live, while I am a manager at the store a town over.

    I went in to meet her more personally today. We talked for a few minutes about work. I think she is just wonderful in every way.

    In the world of social media, I did a search on her before I went to her store. We have a few friends in common and I went to college with her cousin. Her profile is plastered with pictures of her children, but no father. She has two kids. Nothing about this bothers me at all. I just don’t really know how to approach her. Do I take the friend approach for a few months or just ask her out soon?

    I perhaps dug too deep and found out that her former boyfriend or husband (I see no evidence of this) is a former pro athlete who was in the minor leagues of major pro league. He is literally thousands of miles away now with a different girlfriend, pictures of GF with my crush’s kids. Posts saying he is happier than ever blah blah. Real bad guy. I don’t know how bad it was. I could reach out to cousin before I pursue it further, which I barely know her and don’t want to do.

    I am 29 years old. She is two years younger. The jerk has been out of the picture for over a year now.

    I really barely know this woman and just want to get to know her better. And, hopefully, date her, love her and give her everything she deserves.

    Please reach out to me with any advice on how to pursue this.

    • brooke on April 6, 2016 at 3:48 pm

      You should ask her out on a date or for coffee. or as you sggested be her friend. But, either way do something about yoru feelings.

  8. Lynne on May 1, 2015 at 3:27 pm

    I have always been shocked that men don’t always pay when women are paying for babysitters. What is worse is when it is the men that are so excited to express how successful they are. It isn’t a deal breaker for me but it does say a lot about them. xo

    • Emma on May 1, 2015 at 3:56 pm

      Honestly I think it is a lot of cluelessness … they just don’t think about it. Then there are the guys who say, either aloud or to themselves — “It’s not my responsibility to pay for HER kids.”

      Well, no, it’s not, but …

  9. Luchia Dragosh / FabSingleMom on April 29, 2015 at 5:58 pm

    Hi Emma,
    I love your blog. Number 8 and 9 made me laugh. I was told few weeks ago by my friend that I look good for a mom. WHAT??? Is this a compliment because for me is not.
    I joined Ok Cupid a while ago and was chatting with this nice gentleman (so I thought). Out of the blue one night, he asked me to come over. We never talked on the phone before or saw each other.
    I wonder what the reason is, they don’t have common sense or is just hard to date a single mom?

    • Emma on April 30, 2015 at 2:20 pm

      Oh, dunno – maybe that one is just clueless in general, and a single mom walked into his line of fire???

  10. Carla on April 28, 2015 at 7:57 pm

    Love this – 1,2,5, and 6 are my favs. You need to seriously print this list on calling cards us single moms can hand out. Or put in a JPEG that we can add as a profile pic. Only one I’d add: don’t assume I’m unhappy, desperate, or chasing a husband to rescue me.

    • Emma on April 29, 2015 at 7:04 am

      I’ve seen some really off-color behavior (“Do you masturbate when the kids are home?”) but mainly these are good dudes who are just inexperienced dating moms and don’t know the ropes. Hope this helps!

      • Lynne on May 1, 2015 at 3:25 pm

        I have been asked this so many times! OMG!

        • Emma on May 1, 2015 at 3:56 pm

          really!!?!?!?!

          I thought that was so weird / wrong ….

    • Anonymousmama on April 11, 2019 at 12:12 am

      On my second date he told me I have a good reputation to uphold I wouldn’t want to be seen with ur son.

      That pissed me off any comments?

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