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! 

==> See below: 12 things never to say to a single mom on a first date

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

Dating a single mom

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.

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!

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.

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.

Ask her out ASAP

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, give her 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

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 down and out

Maybe she is broke, but don’t assume.

It will piss her off.

Don’t assume her 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.

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

Should you date a man who doesn’t see his kids?

Top dating sites and apps for single moms 

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.

Emma Johnson is a veteran money writer, 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, REAL SIMPLE, Parenting, USA Today and others.

The Kickass Single Mom: Be Financially Independent, Discover Your Sexiest Self, and Raise Fabulous, Happy Children (Penguin, 2017), was a #1 bestseller and was featured in hundreds of media, including The New York Times, Wall Street Journal, Fox & Friends, Oprah.com and the New York Post, which named it to its ‘Must Read” list.

Her popular blog Wealthysinglemommy.com, and podcast Like a Mother, explore issues facing professional single moms: business and career, money, sex, relationships and parenting. Emma regularly comments on these topics for outlets such as CNN, Headline News, New York Times, Wall Street Journal, Fox & Friends, CNBC, NPR, TIME, MONEY, O, The Oprah Magazine, Woman’s Day, The Doctors, and many more. She was named Parents magazine’s “Best of the Web,” one of “20 Personal Finance Influencers to Follow on Twitter” by AOL DailyFinance, “Top 15 Personal Finance Podcasts” by U.S. News, and “Most Eligible New Yorkers” by New York Observer.

A popular speaker on gender equality, Emma presented at the United Nations Summit for Gender Equality.

Emma grew up in Sycamore, Ill., and lives in New York City with her children.

32 thoughts on “Tips for dating a single mom (12 things NOT to say)

  1. 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.

    1. 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!

  2. 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?

  3. 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

    1. 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 …

      1. NO IT’S NOT THEIR RESPONSIBILITY to pay for someone’s else’s spawn. WTF do you NOT understand about that. They have a father and your delusional attitude is one of the many reasons it’s pointless and a very bad idea to date single mommies. I opt out, every time. You deal with it as it’s YOUR problem.

  4. Here’s some advice for men who are considering dating “single moms”: DON’T DO IT. It’s a waste of time and effort. They’ll try to make you financially responsible for their “little mistakes” while killing your love life. There are far better and more numerous options than signing up for the single mommy pity party.

  5. Here’s some dating advice for single men (and women) considering “dating” a single mother (or, alternative, a single father who has custody which is a VERY rare animal indeed) to NOT do this or embroil yourself in this chaos and ridiculousness:

    1. There are a myriad of other options available rather than single mommies.
    2. Date younger women, as they are less likely to be single mommies.
    3. Schedule fun trips that are “child free” which will discourage a single mommy.
    4. Be firm and reject the advances of a single mommy.
    5. Don’t give money or pay for the children of a single mommy.
    6. Don’t allow “friends” to set you up with “very nice single mommy”. It’s just as bad as being set up with “very nice woman” they don’t show you a picture of, because she’s fat or unattractive.
    7. Don’t be a “white knight” and try to “save” these single mommies. They chose their path.
    8. Always take responsibility for your own birth control (and protection from STD’s) and NEVER believe a woman when she says “I’m on the pill”, or “I have an IUD” or a similar statement. PROTECT YOURSELF.
    9. Don’t get married as it’s a very one-sided business deal with only downside if you’re a man. It’s the merger of 2 VERY unequal corporations into 1 where you have few, if any, rights as a man. I required a prenuptial agreement from my ex-spouse and it was singularly the smartest move I could’ve made.
    9. Marriage and/or cohabitation DON’T make a relationship better. Under the best conditions and circumstances it’s a lateral move and a 54% divorce rate tells you all you need to know about the “success” of the institution of marriage. Typically, marriage makes a relationship worse. Name 1 person who can tell you they had more sex and/or a better “relationship” after marriage. It’s as rare as hens teeth, it doesn’t happen.

    Class dismissed.

    1. Class dismissed! For that to happen you actually need to posses class in the first place. We get it, you got burned by a single mother, that sucks; I feel for ya. But you are categorizing a multiple woman, because of the actions of one dumb, lazy biatch. Simmer down, I know they are all not like that; because I found myself a gem.

      1. I am in shock reading this! Im a single mom of two beautiful children , and have never expected anything from a man i date other than loyality and companionship ! I dated a younger guy only to realize he was using me not the otherway around! Because my time is limited from a full time job and taking care of my two children i dont have time for games or bs! It makes me very sad that you would put such a harsh label- its like saying all men are cheats, and abusive- some of us are actually very good woman whos relationships simply didnt workout! I was married for 20 yrs to my high school sweetheart – it didnt work in the end! We arent enemies nor do we wish eachother bad! I dont know who you dated but it sounds like you could use some counseling to overcome your anger towards a single mom!

  6. 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.

    1. 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.

  7. To judge all “single moms” with this spewed hated towards them makes you a judgemental asshole! Realize that some of us single moms don’t need you in their lives… We may ” want” to come in our lives bit need?!!!! No you aren’t needed with your attitudes. Stop judging people with your limited experiences and just maybe us single moms will stop assuming your assholes looking to get an “easy lay”… Fuck off boys cause that’s all you are…..

  8. i love all the restrictions and no no’s and requirements to dating a single mum souns like heaps off fun cant wait………not

  9. You can’t say since this woman did something to me fuck them all that’s no different then being racist do you hate all black people because of one person? That way of thinking will not get you anywhere in life

  10. 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.

  11. 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.

  12. 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?

  13. 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!

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