Single Mom Dating Single Guy

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Single Moms: Date, parent and make money like a mother
By Emma Johnson | Updated Jun. 13, 2021 (originally published Jan. 21, 2020) | 23
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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 woman's are not.
If you landed here, you are likely a guy (or woman) who is attracted to single moms because:
Here’s everything you need to know about dating a single mom:
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:
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.
Helpful tips on how to connect, the logistics, meeting her kids ….
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.
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.
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.
Maybe she is broke, but don't assume.
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.
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.
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.
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.
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.
[If you're thinking of exploring friends with benefits, here's my advice to you.]
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.
She is opening up her life and her whole family's life to you.
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.
Interested in getting to know someone on a second date?
Commit this list to memory and never ever utter a single one of them.
Some real-life advice from members of the Millionaire Single Moms Facebook group:
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?”
A single mom in her 20s might want more kids, just 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.
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.
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 man moms in this stage of life enjoy great, casual sex lives, including with younger men.
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:
Way back at the beginning of my single mom dating shenanigans I fell in love with an older man. My kids were 1 and 3, his were in college. A few months in, I broke it off over a boozy Italian dinner. “Face it,” I said. “You don't want to be running around with little kids again.”
Old story: We kept sleeping with each other, he decided he wanted to try dating a mom for real, and a year later broke it off for reals because he didn't want to date a mom. For a whole bunch of reasons, that breakup was terribly painful for me, and it took me so many months (many of which I admittedly kept sleeping with him. Sue me.) to get over it.
“You're so wonderful, it has nothing to do with you,” he'd say over and over. “It's just that life got in the way.”
I clung desperately to those words for a very long time. But those words are bullshit (even if it was good of him to employ them). Rejecting me because I have children has every single thing to do with me. I am a mom. My motherhood is not a separate island off the coastline of myself. It is part of me. Arguably the very best part of me. I am a mother, exactly as I said I as when I met you online/the office/Starbucks/swing dancing/trashed at your cousin's wedding.
I've bumped into that same floundering position on dating me, a single mom, several times. “I thought I didn't want to date women with kids, but your OKCupid profile was irresistible,” he'll say. What he doesn't say, but what is implied is: “What the hell. I'll give this a try and if I don't like it, I'm outta here!”
I try not to be bitter. We're all human. Can I really fault a guy for liking me so much he goes against his instincts that tell him he's not fit for blended family life? I've got a healthy ego. I'd love to be the one to change his mind!
Yet it's pretty silly that we treat the intersect of romance and children as such an exotic unknown, one worthy of tip-toe trepidation. After all, it's not like I'm raising feral unicorns in my attic, or foster-parenting gnomes. I am a human mother raising human children, the most fundamental essence of humanity, familiar to all, including every single man on OKCupid, who, presumably, was once a child himself.
On the flip side, I do think it is possible to change a guy's mind (though I don't suggest banking on it). A few years ago I had a mini-session with dating coach Kavita Patel, who stands out among her peers as a remarkable insight into dating and relationships overall, and has an intuitive power that is slightly freaky. In telling her about my dating, I said: “If a guy isn't into single moms, that's fine with me. I'm not interested in changing anyone's mind!”
Obvious, right? She disagreed: “Sometimes a guy has to see you with your children. Then he can be open to dating a woman with a family.”
Because she got so much right about me, I could never let that advice go.
Last year for a few months I dated a man who was in his early 40s, divorced but with no kids. We were a mismatch for zillions of reasons, but of anyone I've ever been involved with, he appreciated my motherhood more than any other man.
He also admitted to discounting a relationship with a single mom before crossing my path. One day a few months in he told me he'd watched some Facebook videos of my kids in which I was audible in the background. “You're so natural and honest with them. You're an awesome mom,” he said in an uncharacteristically vulnerable moment. “I adore you.”
Which is exactly what every single mom wants to hear very most of all.
Fast-forward to today, and I am in a 3-year relationship with a dad who loves that I am a mom, enjoys long days with me and my two kids, running between soccer games and theater practice and sleepover drop-offs and the rest — more than I do myself, often. He's hot, successful and my friends join me in thinking I won the jackpot.
When, a year or so in, we had a big relationship talk, and voices went low as two middle-aged people who have been through the ringer each made our best efforts to put baggage aside and be vulnerable in our needs, he held my hand across the dining room table as my kids slept in a room adjacent, looked me in the eye, and said:
“I just want us all to be a family.”
Ladies, here is a huge favor I will do for you:
I will save you the horrors you will find should you google “date a single mom” on the Internet. There are a lot of sexist assholes out there, and you don't need to know what they think.
I will save you from your fears that no good guy wants to date a single mom. Not only have I dated a lot of amazing men who either don't care that I'm a mom, or love the fact that I am one, I also have met and know of thousands and thousands of women who are also mothers who have found love, fun, companionship and partnership after becoming a mom.
But what do the haters say? All those asswipes who swear off single moms? I will share here to save you the trouble of sorting through that toxicity, and assure you that you don't have to worry.
These misogynists claim single moms only want a sugar daddy to pay their bills.
Primed to attract men, use them for their money and maybe sperm, then dump them.
We will never make time for our man — kids always come first (how and why not to make that mistake in this post).
Used-up, damaged goods, and the like.
You know, stuff that children say when their feelings got hurt and they are too underdeveloped to manage their feelings. So they lash out.
Nothing that an evolved woman has to worry about.
Ever thought about online therapy? Way cheaper, convenient, private by text, voice or video counseling — perfect for single moms. Top online therapy sites — which is the best?
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!
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.
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.
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.
This is literally the dumbest shit and worst advice I have ever read…
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
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