Guide To Dating Single Moms

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There are two under-the-radar comedies that are off-season now, but worth the binge as we await their return: Showtime’s SMILF and FX’s Better Things. Both shows have very similar conceits: women hilariously navigate work, dating, family while also raising children alone. They also share DNA in that they’re both semiautobiographical accounts of their stars – Better Things’ Pamela Adlon and SMILF’s Frankie Shaw – who are both working non-A-list actors; each show depicts them enduring the audition process for shitty roles that’ll help keep the lights on.
The elements involving the main characters navigating the dating world resonate with me on a personal level, as I’ve dated more than a dozen single mothers since I was in my mid-20s. I’m sure that people might look at my track record and assume that I’m out here with a fetish sniffing out women with offspring like a truffle pig.
Not the case. I’m not consciously seeking the myriad challenges that come with dating someone with one or several major sentient responsibilities that aren’t a pet. Perhaps they’re attracted to me because they can sense that I have the constitution of a man who was raised, in part, by a single mother. I suppose whatever degree of patience and empathy that’s necessary to enter into a relationship with a single mother is intrinsic to me.
Like many people, I’ve always been attracted to the idea of starting a family with someone who never had a child from a previous relationship, but I got divorced before that could happen. However, being that I’m in my late 30s and typically date women close to my age, I recognize that most of us carry with us baggage from a life well lived. It’s harder to be as picky about dating childless, never-married people than it is when you’re in your 20s…and why be picky about it anyway?
Truth is, I’ve dated some fantastic single moms whose children didn’t deter me from considering a potential long-term relationship with them. I wouldn’t suggest a grown-ass man pass up a potential partner just because she’s already a mother, but there are a few suggestions I’d offer in terms of dating them if you never have – and even if you have but you just don’t know what the fuck you’re doing.
Don’t bitch about canceled dates: Think about what you have to do to get out of the house for a date: Brush your teeth. Apply deodorant. Put on a shirt that doesn’t smell like you threw it on right after leaving the gym. Toss a few sprinkles of water on your balls in case you have a shot at getting your bean wet. Done. Now think about what a mom has to do: on top of all the additional shit society requires of her to look cute for your hapless ass, she has to secure a babysitter, probably get the child fed and ready for said babysitter and wait for them to arrive.
Any of those moving parts can collapse at any time. If that happens and she has to cancel the date for whatever reason, charge it to the game and get over it. She will feel terrible about it, but don’t you make her feel terrible about it. In fact, if you play it well and extend the proper empathy, you’ll earn all the brownie points in the world for the rescheduled date.
They don’t suffer fools as gladly: The beauty of being child-free is that you can fool around with any ol’ poop-butt idiot knowing that they’re your burden alone to shoulder. But many, if not most, single mothers have to consider the additional implications of dating a man who will someday be introduced to their child. Of course, any woman you date with an eye on building a family will size you up as a potential dad, but there’s a difference when that child is already in existence and she can concretely determine whom she does and doesn’t want around them.
So, if you get cut from contention because you bring all the fantastic qualities except that of a good dad, embrace that and think about what it means for you going forward. If you’re nowhere near wanting to be a father to your own child or someone else’s, that’s totally okay, but she’ll pick up on that quickly.
You can’t do anything about the baby-daddy: Unless your lady is the living reincarnation of the Virgin Mary, assume that her child has a father somewhere and that you’ll have to deal with him at some point if the relationship becomes serious. Single dads exist in a wide spectrum – from the doting, involved father who is also open-minded and happy to have another positive man in their child’s life (read: unicorn) to the father whose name you’ll never hear uttered because he literally may as well have just been a sperm donor. (My personal favorite: the mom who told me that her daughters’ father was getting out of jail within weeks.)
You’re more likely to get someone closer to the middle of that spectrum, but assume that you will have to bend to at least a couple of his whims if you plan on being around his children. Of course, your woman’s relationship with her ex – along with any court-established edicts – will play a significant role in the whole dynamic, as well as any headaches it may cause.
Don’t lean into the disciplinarian role: I’ve had several step-parents in my day, and I’ve encountered a handful of boyfriends and girlfriends from both of my parents, so I know about discipline done terribly. And it’s remarkably fucking easy to do it terribly.
Unfortunately, you might wind up in a weird catch-22 at times where you’re expected to dad it up even though you’re not really the dad. For example, you won’t have as much leverage over the disciplinary methods used on the child, which is like entering a foot race with a sliced Achilles tendon, especially if you’re dealing with some challenging-ass kids who could benefit from an occasional elbow to the temple.
Obviously, there are levels to this shit: if you’ve married her and you’re all one big happy family, you’ll likely have more capital to exert your brand of discipline. But there might always be some degree of a disconnect there if little Tyrone Jr. didn’t hail directly from your nuts. So, if you like her but really loathe her kids, you have a decision to make. Just make sure that decision doesn’t have you in handcuffs and on the 6 o’clock news.
Moms like to wild out, just like you: Even though the Bad Moms films comically disabused us of the notion, I still think a lot of guys view single mothers like a cross between pre-school teachers and fine china: their sensibilities have completely changed now that they have a crumbsnatcher to look out for, and they’re eternally destined to a future of ankle-length floral print dresses and whisper-spelling curse words.
If anything, single moms have more of an incentive to get out, drink and misbehave than those of us who take it for granted. And there’s often a correlation between the age of the child and desire to wild the fuck out – the smaller the kid, the bigger the glass of wine required. Also, keep in mind that while moms are more selective in picking a partner, they might just be using you for your penis and cuddle skills for the moment. Which, of course, we’ve been doing with women since time immemorial.
Fuck your ego: It’s imperative that you understand – and make peace with – the fact that you’ll always be a distant second as a romantic interest, regardless of how much she likes you. The kid will grow and require less of her attention, freeing up more for you. But if she has really young children and you like her, humble yourself and dig in, because a happy single mother will absolutely spread her happiness your way. If you’re worth it.
Dustin has been getting paid to write for 17 years. He sucks at pretty much everything else. Publications include HuffPost, The Root, Very Smart Brothas, Chicago Tribune, Ebony, IGN and so forth. He's currently freezing his balls off in Chicago.
Hey Dustin,
As a 36 yo single career oriented female with no children, I often find it difficult to date men who don’t have any children at this age. I too have experienced some of the challenges of dating men with children and the stress of dealing with their “baby momma’s”. I have yet to over come these challenges and prefer to date men who don’t come with that type of baggage. I’m hoping to find someone who has decided to wait until marriage to bring children into the world. Hopefully I’m not waiting for ever.
Notify me of follow-up comments by email.
Dustin has been getting paid to write for 17 years. He sucks at pretty much everything else. Publications include HuffPost, The Root, Very Smart Brothas, Chicago Tribune, Ebony, IGN and so forth. He’s a native Detroiter currently freezing his balls off in Chicago.

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How to Date a Single Mom: A Guide for a Real Man
Dating a single mom is a real challenge. But, as challenges go, it is absolutely worth it. You definitely shouldn’t just skip this option because she has kids. Better believe that there are a lot of advantages and benefits that go along with laundry, diapers, and mature life.
Single moms are very attractive because they have special qualities other women simply do not possess. Certain men will more likely get by with a single mom than with any other woman.
A single mom is not just your average girlfriend. She is a mature and independent woman. The amount of her responsibility speaks louder than her age. She might even be younger than you but having a child by her side makes you at least equal. Some things depend on whether you have kids yourself. If you do, then you two definitely have a point of connection.
Single mothers are very confident, loyal, patient, and committed. It is hard enough to have a child but it is twice as hard to have it on your own being a woman. You should remember this before, after, and in the process of dating a single mom. Single moms dating guys have other criteria for their boyfriends. It is obvious that a single mother doesn't look for something that is not serious. So, if you’re not committed enough, you better skedaddle for the sake of her and your own.
Single moms are special because their difficult experience works for their individual growth. Never forget that dating a single mom is a serious responsibility. Relationships with partners ready to make a commitment are serious enough. That’s why single moms are ostracized on dating sites and in life. Single moms dating men have huge demands and cannot instantly place you before their kids because their kids are the most precious what they have at the time, not you. Nevertheless, it does not mean that you can’t become a part of a family. It’s just that the stakes are higher and you will be expected to meet more demands.
Keep in mind that you are a potential candidate for being a stepfather. Think about everything that comes with it. Ask yourself these questions: will you be able to love her child as yours? How will you handle competition with her child and the role of provider? Single moms are very caring. They are naturally more caring and can make you feel really comfortable. You can also have a lot of time for yourself because even in the early stages of your relationship there won’t be a lot of time for just you two. Be ready to skip the passionate part and think again if you really are ready to make a commitment.
Single moms are very loyal. They understand how difficult it is for you to accept not only them but their children as well. Even though it all might seem positive and optimistic, a lot of people, counselors say, fall apart because they are unable to fit. So, not to cause stress, always keep in mind what you are doing and why. Surely, an innocent child is not a reason the two grown-ups in love cannot be together.
Single moms are special because they do a double amount of work. You will be amazed by her ability to organize, plan, clean, cook, and handle everything. That means you will be expected to keep up and do as much as she does which is probably more than you do now. Having a kid is a responsibility that changes a woman motivating her towards self-growth. It means that she already made some important life choices like having a family. Do not hesitate and act like you don’t think about your future. The question is not about whether you’re in your thirties or twenties because having a kid is a central point. You will be tested on your ability to be a father.
Tips for Dating a Single Mom Dating a single mom is not all about responsibilities. If you play your cards right, you might experience some incredibly pleasant benefits. For example, because single moms are more experienced they can do a lot themselves giving you time to do your own things. It is not at all like dating a girl who doesn’t know how to deal with an internet cable or coffee machine. A single mother would most probably do these and a million other things herself because she can. Single moms also do more because they are independent and because life made them rely on themselves. Here are some other tips for dating a single mom.
Never talk bad about her ex. You simply can’t do it because he is probably still a huge part of her life. In any case, she is seeing him regularly. Finally, you don’t want to create tension between her child and the father. Your first and most important role is husband provided that her ex is alive and well. Even if she has a full custody and does not talk to him, still better be quiet about her ex and do not yell a classic mistake: “it was very bad of him to leave you”. If you have the urge, do it when there is no child around. Still, you better not because she knows him much better than you, anyway.
What you need to know about single mom and dating is that it can significantly improve your life. Don’t listen to the clichés such as “she has a burden too heavy for you” or “her child is not your child”. Think of it as a challenge which can encourage you. Responsibilities come with benefits. These benefits include your potential growth into a family man. You have a unique opportunity of trying to understand what makes your own family feels like before involving yourself in it completely. Try it and stick to it if you like it. But don’t make a common mistake and just avoid women who are much more interesting than most of them.
You Can Learn How to Be Around a Child
You can try being a father before actually becoming one. This is a truly rare chance. Some men think they want to be fathers until they actually become ones. In our days, not everybody is fit to be a parent even though we are naturally predisposed to it. Think of this advantage: you can train to be a father and in the process of training decide whether you want a family or not.
Before going on a date with a single mom, think about everything that was said before. Put on your best suit or clothes which make you comfortable. This advice is universal – always be confident. A single mom is a confident woman. The circumstances of her life made her so. So, you have twice as more reasons to be confident around such woman to appear as a reliable man. Some single moms reported they were asked whether they considered an abortion. You should never ask such a silly thing for obvious reasons.
When you date a single mom, not every typical dating advice seems to work. For example, a single mom is not really interested in the diverse dating experience which includes drinking, dancing, and others ways of going out. She is more interested in you without distractions like watching movies or going to a party. Most probably, you will spend a lot of time at her place because that is where her child lives.
To learn how to date a single mom means to learn how to be a real man. It is one thing to date a girl which may not consider you as her husband. It is completely another thing to date a woman who looks for a man to support herself and her child. Therefore, your role is not that of a seducer or an entertainer but of a supporter. You will be graded on your ability to support a single mother you wish to date.
Learn How to Look Past Her Motherhood
When a woman is dating as a single mom she looks for a new husband. She does not just look for a husband per se. She already had one and it did not work. Actually, she looks for a partner. Logically, she will have more doubts about a new partner expecting him to meet her crucial demands. One of the most important demands is to be desired as a woman. Yes, she is a single mother, independent, self-reliable, responsible, and demanding. However, she is a woman who needs love and care just like anybody else. Therefore, do not treat her like a single mom all the time. Try to forget this fact and be attentive to what you really like about her.
This is the most common advice when the subject is single mom and dating. By befriending her kid you only prove yourself to be good with kids. The benefits of doing so include creating a bond between you and a single mother you are dating. She is more likely to have a connection with if you pay effort to make a connection with her child. Well, at some point you just won’t have any other option but to meet her kids and be friendly with them. Becoming their friend makes her more likely to be attracted to you.
This is also a typical advice. It may sound as a bribe but it works when it is sincere. Pay a certain amount of attention to her child. If you still haven’t met her kid, express your desire to be around her family. Make a present so her child remembers you among other possible partners before or after. It can be something small or something big but do it moderately not to look like you’re trying to buy her kid off. Be wise about what present you make and when you make it.
Spend Some Fun Time with Her and Her Kid
If everything is good, at some point in your relationship you will be asked to meet her kid/kids. You better ask to do it yourself so she would think that your decision is completely honest and sincere. Having her kid around when you spend your time together may not sound romantic. However, the bonding experience will make you feel like a family which is more important in a long-term perspective. Obviously, you can’t ignore her child and she won’t tolerate it. There is absolutely no way for you to love her and not to love her child. So, be a man and act first – ask her out with her kid.
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