Up until now, dating single moms has more or less been a hard filter for me. While I mostly want kids of my own, I’m awkward around them and don’t have much experience with them as I have no cousins or extremely close friends with kids. (For example, I was at a 4th of July party yesterday and a kid came up to me, I awkwardly stared at them, and was like “uhhhh… you want this ball?” My friends had to remind me it wasn’t a dog, hah.)

Anyways though, I got a match I like today, but she has kids. Before I even start talking to her, I’d love to hear some thoughts about what I’m getting into and how it’s different from dating someone without them. Or, like, any red flags I should be aware of that are more common with single parents than it would be otherwise. Thoughts?

26 comments
  1. There will be additional boundaries that you will be expected to respect.

    One of the more typical ones is that it may be months before you ever meet the kid(s). This is more for the mental health of the kids as a revolving door of suitors can be stressful to their development.

  2. Most single moms won’t introduce you to their kids for awhile. If they figure you won’t mesh with their kids they’ll end it.

  3. I have been in two long-term relationships with single moms and a few short term ones. I won’t date them anymore. I actually liked the enforced space apart (since I like alone time) early in the relationship. But once it comes time to take next steps, it’s a darn near impossible spot to be in. For candid insight, I recommend r/stepparents .

  4. Treat her with the same courtesy you’d treat anyone. Don’t expect to meet her kids any time soon. If she talks about them you can ask appropriate questions, but if she seems guarded about them don’t push for information. Make plans in advance and be accommodating of her schedule because of childcare.

  5. Watch out for how she talks about her ex and the reasons for them splitting up. There are always two types of people; ones that were damaged during the relationship and ones that did the damage. Always remember that past behavior will indicate future behavior.

    As for the kid side of things, let her set the pace on anything kid related with your feedback and comfort. Don’t rush too fast unless you are sure. You too can become attached to her kids and the loss of then can impact you too.

  6. My last relationship of 10 years I was step dad, it was an experience and I wouldn’t change a thing. Would i do it again? Idk I’m in my 30s and most women have kids so the pool gets even smaller. I see a TON of videos about avoiding single moms and how it’s such a bad deal for men ” red pill, alpha male, simp bs ” I feel that’s aimed at younger guys because 30 and up the dating pool drastically becomes single parent central. My limit will probably be 1 kid and a clear understanding on the relationship with the father.

  7. While I can’t speak to red flags, what I can say (if you decide to pursue and she’s open to it), is give her space and time. She’s going to be very busy and it will be difficult to manage time for you if she’s got a job, too.

    Offer to support her. Build trust. Get to know her kid, and offer to support them both if the relationship advances (by which I mean, be a good boyfriend to her and a good father figure for the kid).

  8. You’ll most likely have to deal with the ex and that’s some extra baggage you’ll have to deal with. Prepare to do extra work making time for each other. It’s a lot of work and it’s not something I look forward to do. You’ll find out as well. Don’t expect to get up and go on a whim. Babysitters are hard to fetch at the last minute. To me, single moms are a hard pass. I’m burnt out and will never go down that road again. I would not get close too soon

    That’s my take and I’ll let you decide on your own if you’re up for the task. It’s a lot of work

  9. It doesn’t really matter too much in the early dating stages because **hopefully** they aren’t introducing you to the kids right off the bat but after the initial stages, it depends on the individual situation and custody.

    1. Baby daddy. Is he still in the picture? Does he share custody? Is there drama? Why did they breakup/divorce? This sort of defines what your role will be. If the dad is active in their lives they don’t really need a father figure but if he is a dead beat, you might have to take a more active parenting role. Each situation comes with unique challenges.

    2. “Free” days. If it is spilt custody, the mom will be free to hang out with you as if she had no kids about half the time. If she has full custody, you are more or less on the kid’s schedule all the time. Very different situations.

    3. Age of the kids and how many. There is a huge difference in experience between babies, young children, and teens. 1 kid versus 3 is huge.

    4. Attachment. You will probably become attached to these kids and they will be attached to you on some level. It adds another layer of responsibility and consideration to the whole deal. Break ups are extra hard especially if you have been around for a while. You aren’t just dating her, you are joining her family unit.

    5. Travel/activities. Do you like to travel, take trips, road trips, vacations, etc? Well, doing that with kids is a whole different ball game. They have school. They have custody issues. They cost a lot. They have restrictions and limitations. They require constant attention.

    6. Health/mental/emotional issues. All kids are a lot of work but if there are extra issues going on it can really change the game. It can be especially hard if you are the “new guy” and can be a target for a lot of latent frustration and anger that you didn’t earn.

    7. Parenting styles. Depending on what role you are going to be playing it can be difficult territory to tread. You want to be supportive and helpful but not everyone is receptive to it. You aren’t their real parent and your opinion doesn’t hold as much weight with the parents or the kids. Father figure, step-dad, adult mentor, uncle, friend, whatever it can be really difficult to find where you stand in all of it. It can be frustrating and cause problems in the relationship.

    8. What are your plans for your own future and children? That’s obviously more long term but it’s important. Is the mom open to more kids? How do you feel about step-siblings. Can you afford a bunch of kids? Etc etc etc.

    Like I said, most of this doesn’t matter in the early stages and the chances are that the mother will filter you out on her own if there are issues but it is worth understanding what you are getting into.

  10. The thing that helped me the most in this situation when I turned 30:

    25 year old me set a hard boundary that I didn’t want kids or didn’t want to date anyone with kids.

    I also did a lot of maturing and developing between 25 and 30. Now at 35, I would say that 25 year old me didn’t know what he was talking about in 75% of his world, so why be so stubborn on the topic?

    I ended up dating a girl with two kids and falling in love with the kids. You really gotta figure out what you don’t want about children. Everything is going to be new for you.

  11. I’m a single mom. I love my daughter, I prayed to be a mother my whole life. I am so damn awkward around children who aren’t mine though, including my nieces and nephews lol. Up until a certain age, kids are entertained by most things. I just started dating and I just told my boyfriend he’s not a dad/expected to act like one, just be nice and genuine etc and be himself. If we get serious and want to marry later on, yes I would expect him to be more of a dad, but like all relationships his and my daughters will just grow overtime. Also I think part of the reason I’m awkward around kids is that I like intellectual conversations and small talk isn’t always my favorite (talking with kids is going to equate more to small talk). However, with my own kid, I know what makes her tick, I know what she loves and what makes her happy and I love playing with her and making her happy. It’s easy with her because I have a bonded relationship that takes a lot of time (she’s 3.5yo).
    I say just take everything one day at a time and it’s okay to be honest with a woman that you feel awkward around children and would love guidance about her kid(s) and what they like and dislike. I like when my boyfriend asks about my daughter and shows genuine interest because she’s my world and I talk about her a lot.

  12. You don’t focus on her kids. You focus on her first, which is what she’s likely missing the most when everything else in her life is kid focused. Get to know HER, and talk about HER, not her kid especially since you cannot relate then don’t try to have kid talk.

    You won’t even meet her kid until later on when she trusts you enough to meet them anyways. Acknowledge that she has children and make it known, but no need to pay any attention to them until it’s time. She’ll likely guide you with her child that she knows best anyways once it gets there, if it gets there

  13. Just treat the kid like an adult. the kid will appreciate it and the mother will wonder wtf you’re doing.

  14. I’m a single mum and have dated men that thought they wanted to date a mum but weren’t up to it. Some considerations:

    Her kids will always come first. This means that she might have to cancel or move things to accommodate her kids.

    The kids Dad might be a part of their life and there may be drama that comes with that if they’re not on good terms.

    She’ll probably want you to meet their Dad. I guess what I’m saying is that you have to be ok with meeting her ex. He is the kids Dad first but he’s still an ex and feelings of jealousy may arise.

    Consider the kids schedule. Are you able to take weekends away with/without the kids? What about long vacations? I dated a man that took 2 month long holidays once a year. I wouldn’t be able to do that and on his first trip I felt left out (no fault of his own and I encouraged him to go but I still felt a bit sad.)

    Financials: does she pay/receive child support? Kids cost a lot of money. How will you split costs?

    What role do you both want you to have in relation to the kids? Are you allowed to discipline them?

    Who is responsible for the day-to-day tasks and tidying up after the kids? I see sooooo many posts on the relationship sub asking what they can do to make their spouse clean or take on some mental load. It’s really sad.

    Some of these things are usually not thought of until later in a relationship without kids but I think it is super important to be on the same page about how you want you lives to look and what your values, deal-breakers, and non-negotiables are.

  15. ‘mostly want kids’ – but no idea what kids are like. Ehmm… Why do you even (mostly) want kids?? Is it like with microwave and dishwasher : people in the neighbourhood are starting to get them, they might be good for something. And if not, well… Everyone has them, it’d be weird to not get one? (don’t get me wrong, dishwashers are awesome)
    But to give an actual advice: why not ask this woman you just matched with: hey, I never dated a single mom, what can I expect? What’s the worse that could happen? (I know, she could kill you. Still, it’s highly unlikely. Let’s not worry about that.)
    Also, your story reminded me: one time I was training the dog of a friend when her niece came over with her young children. They got interested so I started pretending they were dogs too and I started training them as well. Ffw a couple of months, turns out pretending to be a dog became a regular game for the boy. (i really feel like I’m doing my share in the takes-a-village thing XD)
    Children are people. Single mother are people. Be kind (not nice, kind).
    And please, do not ‘mostly want to have kids’ without any knowledge about what that means. Impregnating a woman will not magically turn you into a dad. It might just be another single mother in the making.

  16. Single mom here!

    – Talk about expectations regarding marriage, your future role in the kids’ lives, potentially having more children, etc early on.

    – Be flexible with your time, especially the first few months before you meet the kids. She might not have as much availability and have to date around her parenting schedule.

    – When deciding who pays for dates, remember she might already be paying a lot for a babysitter. (Not saying she should never pay at all… just maybe don’t insist on going 50/50 on dates haha)

    – Offer to HELP whenever you can! My new guy is always looking for ways to make my life easier. He got a carpet steamer and he’s coming over tomorrow to help me with it. He takes my trash out when he leaves my place. He helps with dishes. He helped me find a good donation center when I purged my house. It is SO NICE to have someone who makes my life easier.

  17. 3 tips that will guarantee happiness and the best possible outcome:
    1. Run. 2. RUN. 3. RRRUUUNNN.

    But this is coming from someone who doesn’t like kids. So take from it what you will.

  18. All these dudes on here talking about passing on single mom’s… Leaving more for all the single dad’s like me!

    Early on only real difference is her time will be harder to get so be happy if she is giving that to you. Other things are normal decent human being stuff that just gets amplified a bit. Be honest about what you’re looking for and what the relationship is. She might not want serious. In fact decent chance she’s needing a bit of an escape from every day life from time to time. So if you’re just looking for fun it doesn’t mean you need to move on, just make sure she knows too.

  19. You must pick a fight with the dad to display dominance, there by replacing him

  20. Yes, dont or double bag it. If she gets prego, youre down for all the kids getting mcds when you visit.

  21. You have to understand her children will come first. Also, you should have good intentions. Usually single moms have gone thru a lot so if you’re messing with one, know that your actions will affect her children as well. Be respectful, be patient and be sincere. If you can’t handle this, you should leave her alone.

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