14 tips for guys interested in dating single moms

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

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 single moms. 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.

Here are my tips for men who want to date 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. 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.

sell engagement ring

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 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.

Other 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 

15 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.

27 thoughts on “14 tips for guys interested in dating single moms

  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.

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