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:
- 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.
Here’s everything you need to know about dating a single mom:
- What single moms want in a man?
- How to ask out a single mom — and how to date her!
- First date tips — what not to say to a single mom
- Problems dating a single mom: what you need to know as a man
- Problems dating as a single mom: what you need to know as 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.
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.
How to flirt with a woman
Seeking advice on flirting with a woman is as old as time — the answers are in general:
- Be yourself — sincere, honest and confident (even if you have to fake it till you make it).
- Show genuine interest in her.
- Make her feel special for who she is.
These Reddit threads have good advice:
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.
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.
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.
[If you're thinking of exploring friends with benefits, here's my advice to you.]
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.
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.
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:
- “You look great for a mom.” That. Never say that.
- Don't ask to come over when her kid are asleep. Just don't.
- “That’s great your mom lives in town so you can leave your kids with her on weekends.”
- “I am really loving this time of my life since my kids went away to college.”
- “Wow, you look good considering you had two kids.”
- “Kids need a man in the house.”
- “You had a C-section? That’s awesome.”
- “You don’t even have stretch marks!”
- “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?”
- “Did you get your tubes tied?”
- “How much child support do you get?”
- “When guys marry single moms and their daughters grow into teenagers, I don’t know how they can control themselves.”
- “My ex has a lot of issues so I really want to get married so my daughter has a new mom.”
- “Do you masturbate while your kids are home?”
- “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.)”
Benefits of dating a single mom
Advice for dating a single mom in her 20s
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.
Advice for 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.
Advice for 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 man moms in this stage of life enjoy great, casual sex lives, including with younger men.
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!
Problems dating a single mom: what you need to know as a man about why dating a single mom is hard
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.”
“I don't want to date a mom”
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!”
Could I change his mind about dating moms?
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.
Related: The benefits of dating single dads
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.”
Problems dating as a single mom: what you need to know as a single mom
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.
We are all gold diggers.
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.
Carry on, you find thing.
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?
Thinking of dating again as a single mom, but not sure where to start?
Dating sites used by single moms and dads
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!
Matchmaker sites for single parents
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.
- It's Just Lunch is 28 years old, reports 3 million first dates (!) and thousands of relationships and marriages
- Guaranteed number of dates. They quote you a custom price that includes a fixed number of dates over a certain period of time (you can pause your engagement with penalty for any reason — including finding love 😍)
- Each package 2 free one-on-one personal dating coaching sessions
- Daters tend to be in their 40s and older, so lots of successful men who have kids and are open to moms with kids and successful careers
- You are assigned a designated matchmaker who goes through rigorous training, and has years of experience — so their intuition is high!
- Both parties pay and invest in the service — so everyone is equally invested in finding a quality relationship (and can afford the 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.
Of course, there are tens of millions of single moms in the United States alone, so 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.