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Dating a single mom? Tips for dating and 15 things NOT to say

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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’re looking to date a single mom, use code WSM25 to get 25% off an eharmony membership >>

Here’s everything you need to know about dating a single mom:

What single moms want in a man

Of course, there are tens of millions of single moms in the United States alone — far be it from me to generalize all of them! Some want a fabulous, low-commitment physical connection. Others are looking for a fun date, a hiking partner, or someone to share a hobby with.

If we're talking about a serious relationship, here are some common themes that I hear single moms seek out in a man:

  • Reliable. Single moms have a lot of responsibilities, and have little time for people who cancel last minute, are late, or otherwise don't do what they say they will. Is this you? Next!
  • You're a good listener — and talker! Single moms often complain of loneliness, and lack of adult conversation. She may need a break from being needed and listening, and would love to be heard. But also don't expect her to carry the conversation.
  • Have your life together. Of course not everyone is at the top of their professional/fitness/personal game all the time, but in general you have a job, a grip on your personal finances, take care of your body, keep your house tidy, and are in general an adult.
  • Low drama. If you're wrapped up in a high-conflict ex mania, that just says you are really emotionally not available to the woman you are interested in. She likely has an ex, too, and can't handle a lot more conflict.
  • You are an equal parent. Now, I know very well that family courts, our culture and society are sexist, and marginalize fathers, and this is a travesty. Perhaps you have minority time with your kids, or are alienated by the other parent. However, your current love interest wants to see that you either do have, or have fought hard to have equal time and take equal responsibility for your kids. Otherwise, you are sexist and that is not OK.

Emyli Lovz, co-founder of emlovz, a dating coaching and matchmaker service based in San Francisco, says based on her experience, these are some things single moms are looking for in a man:

  • He's understanding
  • Has his life together
  • Financially secure
  • Emotionally available
  • Provides safety and stability 

This is what real single moms are looking for in a man, from Facebook and Reddit:

  • “I was a single mom for a time between my divorce and my current husband. He won me over by understanding my children were a priority. Understanding that no one would be meeting my kids unless I thought that relationship was really going somewhere and that meant my availability would be very limited. With my situation my girls' dad is very involved (50/50). They had a dad and he wouldn't be a “replacement”. It also meant understanding that I would be in frequent contact with my ex and remembering that he's an ex for a reason. Meaning that even though we may message about the kids and see each other that there was no romance there so acting all jealous and making demands was a no. Being thoughtful with the kids and making an effort.”
  • “Don’t approach dating a single mum as being an instant family. I dated a few men who gave that vibe and it instantly made sure they never went neeeeear my kids. Not that any man did as I was dead against men meeting my kids unless I was sure and the only man to ever meet them has been their dad most of their lives and we’ve since had another with one more on the way. Flexibility matters. I was always prepared to drop and run on him if I needed to get back to my kids. If I got a call saying I needed to get to them I went, he had to be understanding of that because no matter what kids come first. If he’d expected to come first he’d have been dropped like a ball. Has to understand that ex is in the picture for life because, kids. Time was also mega limited as bio dad isn’t a regular over nighter for the boys. He could go a month or more without seeing me. We could call and chat etc but unless I actually had free time there wasn’t the ability to spend time together. It’s harder by far in those circumstances.”
  • “In both a man and a relationship; mutual respect, loyalty, care and independence. The last means that we aren’t relying solely on each other for friendship, support and engagement. Go out with your friends. Have hobbies or interests I don’t necessarily share. We can have a happy healthy relationship where we don’t have to share everything all the time.
  • Someone who is goal driven, kind to everyone, can manage life on his own, emotionally & financially stable, communicates, respects me & my choices and doesn’t need my constant attention or question my every move. In a relationship: respectful of our time and goals, encouraging, loyal, willing and able to communicate and work through things, has a few of the same interests so that we can spend some quality time together or be able to have things to talk about.

What should I know before dating a single mom?

Moms are human women just like other human women! Single moms do face a lot of societal pressure to martyr themselves for their children, to shield their kids from any man they date — as well as remarry ASAP. That said, more moms than ever are dating freely and confidently, as well as paying their own bills.

So, just date her — no special qualifications required.

8 rules for dating a single mom

Benefits of dating a single mom

What are the benefits of dating a single mom? This is what real men on Reddit have to say:

  • “I love kids and would get to be an influential part of their lives. I would also be able to see first hand what kind of parent they are so I can see if they’re the type of person I would want to have kids with.”
  • “They always have snacks.”
  • “you get to help parent their kid and be a more proactive parent in that child’s life than their original parent most of the time. i hear all the time about kids saying that their stepmom or stepdad was a huge part of their upbringing and that they see them as a parent because they were that important to them, and they credit a lot of their successes as a person to that person.”
  • “The mothers tend to be more mature and secure, and it's not something I put a lot of thought in to – aside from thinking about the added and steadily growing responsibility of helping with the child.”
  • “I think for some men, if you already have kids, it takes away from the “baby fever” some women get. So there's less pressure to 100% commit because that “hurdle” is out of the way. Bro science, could be wrong.”
  • “I just got out of a relationship with a single mom. She had a 5-year old. For me, her daughter was the best part of the relationship. It was brand new for me and scary but it added so much meaning to my life. I am someone who has always thought he didn’t want kids but this experience changed my opinion dramatically. I also thought to myself many times that this could be the perfect way for me to have a child in my life but not actually have to commit to making one myself. If things had worked out with her mom I think this would have been true. I would definitely date a single mom again-the biggest thing is making sure there’s no drama or lingering feelings with the other parent. Which I suspect is kinda rare.”

How to ask a single mom out — and how to date a single mom

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

1. 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.

2. 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.

3. 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.

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

Maybe she is broke, but don't assume.

5. 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.

6. 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.

7. Be patient 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.

8. 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.

Why I don't live for my kids — and that is my biggest gift to them

9. 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.

10. 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.

Cheap and unique date night ideas

11. 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.

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First date tips — what not to say to a single mom

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 15:

  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.

First date tips — good conversation starters

Some real-life advice from members of the Millionaire Single Moms Facebook group:

  • Comedianne Whitney Cummings shared her ‘Red-Flag Dating Test' on Jimmy Kimmel for good questions and conversation starters for a first date:

1. “What’s your favorite color? How would you describe it/Why is it your favorite?”

2. “What’s your favorite animal? How would you describe it/Why is it your favorite?”

3. “What’s your favorite body of water? Can be as specific as Lake Erie at 7am, or as general as the ocean. Why is it your favorite/Describe it?”

BONUS: “If you imagine yourself waking up in a completely white room with no windows or doors, how you would feel?”

  • “Books currently reading, places lived/traveled, movies, and football for me. I try to steer away from what you do as I live in DC and that’s all most folx care about.”
  • “I usually tell a story about something funny I did with friends and that usually leads to more story telling…unless they have the personality of an empty dinner plate then it may go nowhere!”
  • “I like to ask if they know what their love language is… tells me how they best receive affection AND that they've done self work both of which are important to me. I've also started throwing in asking what their attachment style is.”
  • “What invention are you most frustrated you didn’t think of first? (Mine: individually wrapped toothpicks and pool noodles.)”

What to expect when dating a single mom

Insights when dating a single mom in her 20s

A single mom in her 20s might want more kids, just be starting her career and/or going to school. Or, not. She is young, and so is her body, so she has a lot of dating options.

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Insights when dating a single mom in her 30s

A single mom in her 30s might want more kids, could be in any stage of professional and financial security — including being very established in both her profession and bank account. Or, not.

Insights when dating a single mom in her 40s

Probably doesn't want any more biological kids of her own, knows a lot about who she is and what she wants and is likely seeking someone in a similar situation — though many moms in this stage of life enjoy great, casual sex lives, including with younger men.

Find younger men (and younger men, look for cougars) on CougarLife. Read more about younger men dating older women.

Dating a single mom? 3 red flags to watch for

Just like any other person, some moms are not ready for dating. If you are in interested in a single mom, here are some dating red flags to look out for:

  • Talks about her ex all the time. She has not healed or moved on. Even if she co-parents with her kids' dad, she still needs some space and boundaries before she is ready for you.
  • Terrified of her kids seeing or even knowing that she dates. This is a woman whose ideas around dating and sex are stuck in another era — one in which women are either whores or mothers. And/or she is not ready to date and is using her kids as a barrier to being hurt again.
  • She's broke and expects you to fix that. There are indeed gold diggers out there. If that is not your jam, and your woman makes it clear that she has no interest in financial independence in your relationship, bolt!

Matchmaker sites for single parents

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

In this post I lay out the pros and cons of matchmaking experiences.

Bottom line: Is it worth dating a single mom?

I’ve said it before, and I’ll say it again — every single mom is different, and your experience dating one single mom may be drastically different than dating another. That being said, if you are someone who understands and is willing to put the time and effort into dating a single mom, you can have a meaningful and lasting relationship — if that’s what you’re looking for. 

For serious relationships, eharmony is our No. 1 choice dating site because: 

  • A- rating from the Better Business Bureau (accredited)
  • Vetted profiles to prove they are a real person and not married
  • Free basic plan
  • Video dating

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What should I know before dating a single mom?

Moms are human women just like other human women! Single moms do face a lot of societal pressure to martyr themselves for their children, to shield their kids from any man they date — as well as remarry ASAP. That said, more moms than ever are dating freely and confidently, as well as paying their own bills.

Is it worth dating a single mom?

Every single mom is different, and your experience dating one single mom may be drastically different than dating another. That being said, if you are someone who understands and is willing to put the time and effort into dating a single mom, you can have a meaningful and lasting relationship — if that’s what you’re looking for.

Wealthysinglemommy.com founder Emma Johnson is an award-winning business journalist, activist, author and expert. A former Associated Press reporter and MSN Money columnist, Emma has appeared on CNBC, New York Times, Wall Street Journal, NPR, TIME, The Doctors, Elle, O, The Oprah Magazine. Winner of Parents magazine’s “Best of the Web” and a New York Observer “Most Eligible New Yorker," her #1 bestseller, The Kickass Single Mom (Penguin), was a New York Post Must Read. As an expert on divorce and gender, Emma presented at the United Nations Summit for Gender Equality and multiple state legislature hearings. More about Emma's credentials.

24 Comments

As man what I find a problem is having to be around the men who fathered the kids. For a man it’s awkward having to be around the same guys she had relations with and the kid. You can call it “ego” but I believe women use that to shame men.

It’s weird as I don’t know the true relationship being honest goes so far. If she is still hurt over them … why would they tell you it’s pretty much counterproductive for them.

How is a man supposed to feel about that especially if they want a good relationship with their dads. That’s the part single moms seem to forget. I don’t want a friendship nor any interactions that are not necessary . It’s not my relationship and I had nothing to do with it. Should I be subjected in being “good” with it?

Just started dating a childless man…he is a sweetheart but I am having problems balancing both. Seeing him and booking a sitter . And idk how long before either I just decide to maybe move on. He has told me I am welcome to bring kiddos but they are very young and our relationship is very new.

Moms and guys need to be honest with one another. I know this sound redundant. You have to respect and honor eachother. Guys should always be on the alert from woman. Very simple reason, many out there wants a hot guy and to be successful. BUT, but if you look at this woman are overweight or fat and don’t do much. I know people like that. No question that there are fair share of lousy man out there. And I know guys that I would NOT introduce them to my friends either and are fat and lazy.
Real man and a real woman will not put up with medicare people. So be strong and make something good out of yourself and not a blob of fat.

Very interesting article, I am a childless man who is going to try and date a single mother. I saw this out there casually browsing around and it makes sense thank you.

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!

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

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?

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.

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.

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.

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!

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.

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.

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

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 …

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?

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

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.

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!

I dont know why any guy would actually ask “Do you masturbate when the kids are home?” I mean I’m single I seem to be very attracted to single mothers but that would never cross my mind it makes me laugh and cry a little inside that it had to be said because men out there actually ask. Not my business and completely devoid of any tact. Smh.

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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