The Pitfalls of Dating A Divorced Dad

Name: V.divorce
Age: 50
Question: I’m an attractive, well-educated, debt-free 50 year-old widow who’s childless (by choice), that’s been seeing a man for 3.5 years. Nearly all of this time he was legally separated–4 months ago he finally divorced, amicably. He has two children, a 13 year old and a freshman in college. I’m not over-joyed about having kids in my life, but I enjoy their company and have spent many pleasant weekends with them. We’ve recently begun discussing if he should give-up his apartment now that he’s divorced, but as the possibility looms, my concerns over his financial situation deepen.
I know divorce is expensive, but he left the marriage with a lot of old, shared debt ($50K). He makes enough to pay for his modest apartment, considerable child support & alimony, and his son’s tuition at a private college. Yet when it comes to contributing to our home, there isn’t much left to go around! I use “our” because he has, essentially, been living with me for the last two years, returning to his apartment only when his kids visit. While it’s true that I’d have to pay all the bills if I lived alone (he does split the groceries and pay for most of our entertainment) I worry that his kid’s wants–they’re  getting what they need–will always come first (an iPhone for a 13-year-old? Really?).  In all other respects he’s a loving, smart, thoughtful man who seems very committed to me.  Am I being taken for a ride? Or is this par for the course when dating a divorced dad? By the way, we have put together a budget;  by time he pays all his obligations to his children and ex-wife and actually begins to pay his debt down, there’s not enough to pay half his share.

Are you be taken for a ride? Why? Because he’s taking care of his children and not dressing you and furs and diamonds? You’re a grown woman. If you want your apartment to look a certain way, pay for it. It’s not his responsibility. He has responsibilities. Ones he’s legally required to prioritize.Without getting too personal….if you’re a widow…I’d think that your late husband did what he good to make sure you were taken care of, yes? So then..what’s the problem here? I mean..the real one. Because I’m not buying that this is about his financial situation. This goes deeper.

Yes, this is part of dating a divorced Dad. If you want to live together, then you can do what men have been doing for years…pay his way. Cover what he can’t pay in rent. If it’s that important that he makes some move that makes you feel as though you’re a priority, then you’re going to have to pay for it. You rarely if ever hear men complain about having to do this. It’s expected that men do it. Are you paying your mortgage? Or is that coming from money that was left to you? What is your financial situation? You conveniently failed to mention that.

As for his kids and being a priority, I hate to tell you, but this is how it will always be. If he’s not investing in them financially, he’s going to be investing in the emotionally. Will it get better? Sure, a little bit, when they’re out of college. But  the times that you’re in the top spot will be few and far between. That’s just how it is. I don’t know how my step-mother handled it with the grace that she did.

In all other respects he’s a loving, smart, thoughtful man who seems very committed to me.  Am I being taken for a ride?

I want you to re-read this sentence and ask yourself how you are able to say, in one breath, that this man is loving and thoughtful and then in the next question his motives. There’s something not right about that. I don’t mean that in a “Molly, you in danger, girl” type of way. That is a comment about quickly you can go from one thought about this man to the polar opposite. That should really give you pause.  You don’t want to come out and say how you resent his kids because you fear that makes you sound awful. It doesn’t. In fact, it’s pretty typical. I’m sure many people in your position feel the same. You didn’t want children. So you either need to learn how to co-exist with his kids and accept your place in this relationship or you need to move it along.

What you’re looking for now is a statement of his commitment to you. You could always just keep doing things the way you’ve been doing them. It sounds like that has been working for you. If he’s already staying at your place so often, then what’s the difference? That’s why I don’t think this is about wanting to build a home together. This is about you wanting confirmation that you are a priority. You want a gesture from him that reveals that he is just as committed to you as he is to his kids.

He’s not. He can love you and commit to you as a partner but you will never, ever, ever mean to him what his children mean, because those are his children. That doesn’t mean he won’t do everything he can to show you how much he loves you and what you do mean to him. But you can’t continue on in this imaginary race with his kids for his affection. You will lose.



Psst! Like our new Facebook page!

45 Minute One on One Dating Profile Review

Get a 45 minute one on one review of your profile with me.  I’ll go over your picture selection and ad text and let you know if your profile includes any buzz words or red flags. I’ll also help you tweak/write your profile if it needs some freshening up.


  • *Profile analysis (45 minute phone session.)
  • *Assistance with editing and re-writes.
  • *Photo selection and review.
  • *Feedback about specific issues and experiences.
  • *Site selections  and Pros & Cons of the more popular dating sites.
  • *Overview of online dating basics – how to write intro messages, how to draw more attention to your profile, how to sort your searches so you can see profiles you might be missing.

$55 (Use code BLOG to save $10)


Eventbrite - Master & OKCupid


Let Me Write Your Profile For You


  • *A complete re-write of your self-summary and other profile sections as well as what you are looking for in a partner or date.
  • *Assistance with editing and re-writes.
  • *Photo selection and review.
  • *Feedback about specific issues and experiences.
  • *Site selections and Pros & Cons of the more popular dating sites.
  • *Learn how to write better intro messages that will get responses
  • *Get tips to draw more attention to your profile
  • *Learn how to sort your searches so you can see profiles you might be missing.

$95 (Use code BLOG to save $10)

Eventbrite - Master & OKCupid


Related Posts Plugin for WordPress, Blogger...
, , ,

15 Responses to “The Pitfalls of Dating A Divorced Dad”

  1. Speed Says:

    This relationship is doomed. The first problem is the woman’s “child-free by choice” statement and her being “not overjoyed about having children in her life.” I also don’t have children, and I admit that they can be loud, irritating, nosy, illogical and rude. However, they can also be innocent, curious, funny, and excited about life in a way that we adults have forgotten. Doesn’t the OP have any nieces or nephews? People who make snarky or implicitly hostile remarks about children are not people I want to be around. It implies too much negativity, lack of empathy and/or narcissism, even by American standards.

    Secondly, as Moxie wrote very well above, it’s just common sense that a single parent has to put their child first. That responsibility doesn’t end when the kids turn 18, and can even be extended when grandchildren arrive. You will never have a single parent “all to yourself.”

    And in fact, you wouldn’t want that, anyway. A guy who ignored his kids from a previous marriage to focus entirely on you is a guy with very bad character.

    Thirdly, the OP is bashing the guy’s financial situation severely. Yes, money is critical, especially to a man’s status. That said, even affluent guys can be overwhelmed by circumstances—and divorce, alimony and child support are those kinds of circumstances. We men know when we aren’t making as much money as we should, and we’re usually inwardly embarrassed by it.

    All we ask is at least implicit emotional support from our partner when we are trying our very best to make more bank. I don’t think it’s a huge demand. However, this OP seems irritated that her guy isn’t making enough cash and, moreover, isn’t spending enough of it on her.

    Therefore, this OP needs to leave and find a 50+ , wealthy, childless, handsome man with plenty of free time who can be fully devoted to her. Good luck in that unicorn hunt.

  2. JulesP Says:

    OP… his kids are always going to come first! That is the nature of being a responsible parent. And surely you would question his character were he not to put his kids first.

    Agree with Moxie’s take on what you wrote.

    Btw, “iPhones for 13 year olds, really?” yes.. really in the real world! I guarantee you that any 12 year old and upwards use their smart phones to the max and in ways that you and the rest of us haven’t yet discovered..

  3. Rosie Says:

    As a single mom, I’d say that I wouldn’t date a single father who didn’t put his children first. We all have priorities: work, relationships, hobbies. sometimes those priorities might switch spots, but the kids will always be first!

  4. maria Says:

    LW sounds so set in her ways, why even bother dating anybody, particularly a divorced guy with two kids? what do you expect from this guy? sounds like he is being honest with you about his finances and the poor guy is doing what he can. yup, the kids will be a priority. I am 34 and I know me and my sisters are still my parents priority. now that there are grandkids, forget it. You sound like you are just “dealing” with his kids hoping they go away soon (won’t happen unless he is a terrible person) instead of making any attempts to integrate your life with his. If you want to be with him, you may have to pick up a little bit of slack financially as he has a lot more expenses than you do. I also agree with moxie that you conveniently left out YOUR financial situation. It is unbelievable to me that even though you know exactly what he is going through financially with alimony, child support etc that you STILL have the audacity to think you are being taken advantage of. It is so ridiculous. You expect a recently divorced man with 2 children to what? Magically take care of you and your apartment? My advice to you is to stop dating this guy, and leave him be. also if you must date, try and meet an older man with older kids (I am talking kids 25 and older) who may have a little more flexibility or men with no kids at all. You don’t like/want kids and view them as little more than a nuisance no kids should be subject to that. leave this man be.

  5. mindstar3000 Says:

    She’s upset that a father is taking care of his children???

    “… by the time he pays all his obligations to his children and ex-wife and actually begins to pay his debt down, there’s not enough to pay half his share.” Why is he responsible for half YOUR bills?

    You admit “… he does split the groceries and pay for most of our entertainment.” And that’s not enough in view of his diminished financial circumstances???

    The greed and sense of entitlement that the OP has is shocking.

    OP leave this man, he will have no shortage of women who will admire him for his fortitude, and go hunting for that elusive childless man who is eager to subsidize your lifestyle

  6. Lisa Says:

    He’ll have more money if/when he gives up his apartment. But he won’t do that unless you assure him his children are unconditionally welcome in the apartment/house the two of you would share if he gave up his own.

  7. yb Says:

    He sounds like a nice man to have as a boyfriend. You didn’t mention marriage, but be aware that if you did, you would take on his debt and maybe even indirect financial responsibility for his children??? Also, do you leave in a common law marriage state?

    I think letting him move in and devising a financial plan that outlines what he can contribute to the household is a good plan. Of course, you have be flexible and acknowledge it won’t be 50/50. If you are financially comfortable, I do not think this should be a problem. Anything he contributes will be additional.

    To me, companionship & emotional support are very important and far exceed the value of money. Men and women both forget this from time to time.

  8. bbdawg Says:

    If anything the fact that this man is a dedicated father is a huge plus. It speaks so highly of his personal conduct. It would be A LOT worse if instead of getting his teenager an IPhone, he was spending it on expensive clothes he doesn’t need or flashy gifts the OP doesn’t need either. Sorry Iphones are more important than computers these days, guess what that’s a good way to keep in touch with his child!!!

    I think the issue here is communication. The OP sounds passive-agressive. She needs to ask her BF if they are moving forward and moving in together and what, if anything, he can contribute. That’s not unreasonable. If he can’t, he can’t. If you find someone who is a good person, and a great partner as the OP has said,AT 50 + YEARS OLD I am sorry, you stick to that person…money can’t be more important than that. If you go back to the dating world you’ll find that a lot of wealthy men who are childless and over 50 are likely after women in their 30s and younger if they can manage. The grass in NOT greener on the other side. If you find love, at 50+, it’s a good idea to be flexible with what you can.

  9. yb Says:

    You didn’t mention his age?

  10. yb Says:

    I just re read everything. The OP is sensing something is off that’s why she wrote this letter…Moxie is spot on:

    “So then..what’s the problem here? I mean..the real one. Because I’m not buying that this is about his financial situation. This goes deeper.”

  11. Noquay Says:

    Yep, as someone who raised a bro starting when I was 17, kids come first, as they should. Anyone who’d ignore/abandon his children/parents because he feels they’re too much trouble isn’t someone I’d want to date, let alone be in the same room with and I too am (biologically anyway) childless by choice. He’s paying for groceries, etc. Nope, he can’t pay for his half of rent. Who cares? It’s not as though you didn’t have to pay your rent, yourself, in the first place. I too, in my 50’s have no desire to raise kids again, as I feel I’ve done my time in that respect plus am still paying the bills for the care of my deceased dad so I am in no position to caretake. Therefore, I choose dudes whose kids are adults; it’s that simple.

  12. jaclyn Says:

    I lived with a man with young children in my 20s, so I understand the enormous sacrifices you need to make in order to date a parent. In my 20s I vowed to not do that again, but if I become single again when I am older I would absolutely need to be flexible and accept those sacrifices in order to not be single. At 50, you must understand that any relationship will likely come with significant compromises since men have a lot more options at this age.

    It is your life, and your choice as to whether or not to continue the relationship understanding that your bf will not contribute 50/50 to household bills. If it were me, I wouldn’t want to fight over every iPhone/blowout sweet 16/graduation present/ski trip as they come up. If I were moving in with someone in your boyfriend’s position, I would want to sit down and discuss with him what contribution he would feel comfortable making towards rent if he gives up his apartment. And if that amount is something you can live with, I’d move forward in the relationship.

    Also, you don’t mention if you actually own your own home, but if so a less than 50/50 split can certainly be justified since your bf contribution is going towards your long term stability by paying down your mortgage. By living in your home, he isn’t currently investing in a long term financial asset for his retirement (although it would be quite understandable that he cannot do so at this point).

    As someone above pointed out, you should consider the financial ramifications of this relationship prior to marriage, as your income may be considered for child support depending upon the state, and you may be inheriting his debts. I’d certainly consider waiting until the youngest were 18 or getting a prenup to protect yourself, but I wouldn’t have a problem with him moving in even if he can’t contribute 50/50. But only you know what would make you happy so you need to decide if you want to continue this relationship.

  13. Dori Says:

    “But the times that you’re in the top spot will be few and far between. That’s just how it is. I don’t know how my step-mother handled it with the grace that she did.”

    Well, now you know. She was nursing resentment and planning a revenge :-(

  14. Bill Says:

    Ummm… this is a decision the OP should have made three and a half years ago. Ideally, “separated with kids” someday becomes “divorced with kids”, and for a woman wanting a relationship with this man, the “best case scenario” has played out. Him somehow becoming “single with no kids” was never a possibility.

    Reading between the lines, I think she’s saying that this man is her ideal in every way except for his children and the fact that they are a priority to him (kudos to good dads everywhere). It’s either a deal breaker or it’s not, only she can decide. Time for an adult decision.

  15. Joey Giraud Says:

    I’m a 53 yr old divorced dad who puts my two teens at top priority. Pretty strapped for money due to high alimony and child support payments, even with shared custody. Still like women, but not very upbeat about dealing with their expectations and tests. Pretty cheerful and better at flirting then ever, get plenty of interest, but have little to return other then courteous pleasantries. Most definitely feeling gun-shy, twice burned. Still have a drive, but it’s not raging enough to induce me to jump off a cliff like it used to be.

    With I had something more worthwhile to add here. Only commenting because I’m in the titular demographic here.

    OP’s letter reads almost like a warning to not get involved at all.

    Oh yeah, if you’ve got him on the hook, good for you. I know a number of divorced men in my age range who are actively dating, but as many who aren’t and don’t really seem to care much to. Regular guys, not angry MRA types.

    I expect in a few years when both teens are off in college and I have a bit more money, I’ll probably dive back in the shark tank. I keep reading Moxie for inspiration in that direction :)

© 2013-2018 And That's Why You're Single All Rights Reserved