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Dating a single parent? 5+ challenges you need to know

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If you’re thinking about dating a single parent but have some reservations, you’re not alone. You may have heard that single parents:

  1. Will never have time for you
  2. Are still in love with their ex
  3. Only want a replacement parent or financial support

Fortunately, those things aren’t true for the majority of single parents, and you can have a healthy and successful relationship with a single parent if — like any other relationship — you’re willing to put in the time and effort. 

That being said, there are some unique challenges that come with dating a single parent. 

This is what you should know before you start to date someone with kids:

Is it hard to date a single parent?

Amber Lee, a Certified Matchmaker and CEO of matchmaking service Select Date Society, says that dating anyone who leads a busy life can be hard, and dating a single parent is no different. 

“If it's the right person for you, the two of you will find ways to make time for each other,” Lee says.

She says if you’re dating a single parent, you might have to plan dates around the kids’ schedules, which can be affected by things like child custody arrangements and babysitter availability/cost.

However, if you’re willing to be flexible and supportive of your partner’s parenting commitments, dating a single parent doesn’t have to be hard. 

What are the challenges of dating a single parent?

Lee says the biggest challenge of dating a single parent is dating around potentially busy and limited schedules. In addition to dealing with custody schedules, your partner may have to attend after-school activities, school events, birthday parties, etc. 

You might not see your partner as often as you’d like — or you may have to spend a lot of time with her children once she’s comfortable introducing them to you.

Lee recommends helping your partner secure a reliable babysitter and being prepared for last-minute cancellations and plan changes. 

These are some other challenges of dating a single parent, according to Redditors

You might not always come first:

Reddit post about the challenges of dating a single mom.
Reddit post about challenges of dating a single parent.
Reddit post about cons of dating a single parent.

You might not get along with the kids:

Reddit post about kids and dating a single parent.

You might have to deal with a difficult ex:

Reddit comment about mother-in-law involved in dating a single parent.
Comment on Reddit about dating a single parent.
Negative comment on Reddit about dating a single parent.

You might have to take on some parenting responsibilities:

Negative comment posted on Reddit about dating a single parent.

There might be double heartbreak if things don’t work out:

Comment on Reddit about bonding with child when dating a single parent.

Challenges of dating a single mom

Lee says single moms are superheroes when it comes to multitasking and juggling busy schedules. However, these are some challenges you may face dating a single mom:

  • She’s more likely to have primary custody of her kids, so her free time might be limited. According to the most recent U.S. Census data, about four out of every five custodial parents — 79.9% — were mothers. 
  • Her kids might not like you — at least not at first. Take your time, and don’t put pressure on the relationship. If you respect their boundaries, don’t see them as competition, and treat their mom well, they may eventually warm up to you.
  • Her ex might still be in the picture. Even if she has an amicable co-parenting relationship, you still have to deal with the dynamics of having another person in the picture, one you may have to regularly interact with. 

This Redditor had some good advice about the challenges of dating a single mom and how to handle them: 

Helpful advice on Reddit about dating a single parent.

This Reddit thread dispels some of the “horror stories” about dating a single mom: 

One commenter in particular stresses the fact that no two single moms are the same, so you have to evaluate each potential relationship under a different scope: 

Post about dating a single parent on Reddit.

Are single moms red flags?

Single moms in general aren’t red flags. But there are some red flags you should look out for when you’re dating a single mom, just like you would in any relationship.

Lee says the biggest red flag to look out for is a tumultuous relationship with her ex. 

“If they are not capable of co-parenting in a healthy way, your relationship is going to be filled with drama,” she says.

She also says to avoid single moms who don’t have healthy boundaries with their children — for example, if they have trouble disciplining their kids or if their relationship with their kids is more like a friendship than a parent-child relationship. 

“If the kids are the ones running the show, it may be time to reconsider pursuing a serious relationship,” Lee says.

She also says to avoid single moms who seem like they’re looking for a replacement father for their children, rather than a romantic partner for themselves.

“If they seem more interested in you filling a void for their kids than in a romantic relationship with you, don't ignore this red flag,” Lee says.

A Redditor on this thread confirms that point:

“I had a friend who was dating a single mother recently. She pretty much expected him to support her and the baby and kept him on a short leash like they were married and the kid was his. She often relied on his family to take care of the baby too. Single moms obviously can use some support but when you start dating a guy expecting him to become father and husband, especially when both of you are young, is perhaps why some men may be wary of dating single moms.” — Joeblow521

Another Redditor offered this cheeky take on single mom red flags:

Advice on Reddit about dating a single parent.

Why dating a single mom is hard?

Dating a single mom can be hard because your time together might be limited — at least until she’s comfortable having you around her kids. You also have the added pressure of forming a relationship with her kids if things become serious and potentially having to interact with her ex. 

The reality is that women are usually judged more harshly than men in all aspects of life — and single mothers are no exception. 

This single mother calls out the double standards and judgment she’s faced as a single mom trying to date:

Is it worth dating a single mom?

Because no two single moms are exactly alike, there is no blanket “yes or no” answer to this question. 

That being said, these are some benefits of dating a single mom, according to men on Reddit: 

  • “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.”
  • “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.”
  • “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 into – aside from thinking about the added and steadily growing responsibility of helping with the child.”
  • “They always have snacks.”

If you’re thinking about dating a single mom, here are some tips for dating her:

Tips for dating and 15 things NOT to say

Challenges of dating a single dad

Lee says the same challenges that exist for dating a single mom exist for dating a single dad — custody schedules, dynamics with his ex, and having to be respectful of his relationship with his kids. 

“Don't be too hard on the single dad you're dating if he forgets about something and over-books his calendar or has to change plans at the last minute,” she says. 

Why dating a single dad is hard?

Lee says single dads dating often need to be in a relationship that feels easy, where they don't have to add a stressful relationship to their list of responsibilities. 

“Don't expect for a single dad to constantly dote on you,” she says. “Instead, you may need to be the one showering him with love.”

These are some other reasons dating a single dad might be hard, according to the women of Reddit: 

  • He may not want anymore kids because he already has some of his own. You're kind of expected to balance being childfree but also adoring his kids. If you stick around long enough, you will likely be drafted into helping with the kid (free babysitting, helping around the house, occupying them, etc), but you will get no say in actual decisions. That's for the “real” parents. It is a thankless job.
  • He will have a huge financial strain. If he does agree to have more children, they may have less in life than if you had chosen to be with a man without children. Additionally, he may not be all that enthused about kids with you because he's been there/done that, but is simply obliging you because it's what you want.
  • The mom is almost certainly still in the picture. Very rarely do co-parents have proper boundaries. I had the unfortunate pleasure of dating someone with an absolute crazy ex who sabotaged our date plans whenever she could, often using the child as leverage.
  • The person you love the most will never love you the most. I know it's silly, but imagine those (albeit, unlikely) scenarios where you and the kid are both drowning and he can only save one. You drown, every time. You will never be the most important person to him.

Is it worth dating a single dad?

If you can handle the added dynamics of dating a single dad, you can have a meaningful and successful relationship with one. These are some benefits of dating a single dad: 

  • You know what you’re getting in a partner. A man’s relationship with his children is the best measure of his character, personality and partnership potential.
  • Single dads are busy, so they probably won’t be needy/clingy.
  • They might not want more kids — a benefit if you yourself don’t want more (or any) kids.

This is what real single moms had to say about dating single dads: 

  • “They are more mature, responsible, and usually more accepting of your personal priorities such as kids/work. They often crave more stable relationships and know how to balance family responsibilities along with the rest of their lives.”
  • “They understand the responsibilities and schedule constraints of being a single parent. It's also good because you can parent vent to them and they understand.”
  • “They understand the unpredictability of raising kids so if something comes up unexpectedly, they don’t get all bent outta shape if you have to reschedule or cancel.”
  • “I think it is more likely they will be your people, like have very similar wants and needs as a single mother. You go into a relationship wanting compatibility and generally if you are similar-it is more likely to happen.”
  • “If you’re on the same or a similar custody schedule, you can truly devote your time to each other on your off time to really get to know each other, and he’ll understand when you’re busy during custody time. And then you can slowly introduce your kids to each other when you both feel it’s appropriate. He should also be more understanding when family circumstances arise out of the blue and you need to pivot.”
  • “They don't want all of your time – they have their own commitments and responsibilities and (the good ones) are great about understanding and respecting yours, as well.”
  • “They are presumably busy with kids, job, and extracurriculars so they won’t smother you too soon.”
  • “I was actually set against dating anymore single dads due to parenting differences, custody schedules and conflicts etc. and then I met the guy I’m currently dating. Single dad, he is so kind, patient, considerate and helpful. I’m thankful for all the shitheads I had to go through to get to this one because I appreciate him so much. He is the epitome of teamwork and I couldn’t ask for a better partner.”

If you’re thinking about dating a single dad, check out these tips: 

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.”

He agreed.

“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.

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 fined 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 parent, 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 on a man or woman before you go out with them!

Here is our list of the best dating sites and apps for single moms.

Our No. 1 recommendation for finding serious relationships is eharmony because: 

  • A- Better Business Bureau rating
  • Free 150-point personality report
  • Apps for iOS and Android
  • 100% of members are proven to be real (no catfishing or married people!)
  • For paid memberships, eharmony has one of the lowest prices.
  • Video dating

Get 25% off an eharmony membership with code WSM25 >>

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.

Is it hard to date a single parent?

Amber Lee, a Certified Matchmaker and CEO of matchmaking service Select Date Society, says that dating anyone who leads a busy life can be hard, and dating a single parent is no different. “If it's the right person for you, the two of you will find ways to make time for each other,” Lee says.

What are the challenges of dating a single parent?

Lee says the biggest challenge of dating a single parent is dating around potentially busy and limited schedules. In addition to dealing with custody schedules, your partner may have to attend after-school activities, school events, birthday parties, etc.

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.

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