Ask Polly: Should I Date a Single Mom With an Out-of-Control Kid?

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Dear Polly, 

I’ve loved your column for years. As a guy in his early 30s, most letters and responses have given me different perspectives to consider and appreciate.

I spent my 20s focused on my career and myself. I didn’t date, moved often, lived alone, and very rarely put myself out there. Five years ago, I found a job that made me feel I could finally put roots down and start to get serious with a relationship. After a few short relationships didn’t work out over the last couple years, I met someone a few months ago who made me think she could be a woman I might spend the rest of my life with. She’s my age, a single mother, very sweet, attractive, intelligent with a great career. She’s caring and empathetic and we love many of the same things. Conversations come naturally. Things have been mostly great from day one.

Like any relationship, there are some issues. Unfortunately, after having been alone for so long, I simply don’t know if these issues are minor, or legitimate death sentences. My guess is each of these is connected, and when combined they might doom this relationship.

The first is proximity: We met at a bar, and at the end of the night found out we lived in the same apartment building, on the same floor, 50 feet away from each other. There are clear benefits to this. The convenience is great. That said, I’m very much an introvert used to living my entire adult life alone. It’s been a complete shock to have someone always there, if not physically then with the knowledge that in ten seconds they could be. While she initially told me she, too, was an introvert who needed alone time, more and more it’s become obvious that she was at worst lying, at best fudging the truth. While she’s trying to accept that I need time alone to recharge, she really would like me to be there whenever I’m available.

The second is our sex life. Contrary to what many women apparently believe, there are guys out there who don’t actually crave sex all the time. I’m one of them. I know more guy friends and relatives than not who are similar. I’ve never had an emotional connection because of sex and it’s never been a way for me to feel closer to anyone. Sex is a physical thing for me and in the past has been more trouble than it’s worth. I do enjoy it and consider myself a giving and attentive lover, but like a lot of people, I have to be in the mood. It just seems to happen only once or twice a week. My girlfriend isn’t like that; for her, sex is an emotional act. It’s how she feels close to me. For her, the more sex the better, and she doesn’t understand how I can be in love with her while not expressing constant passionate feelings that manifest themselves in bed.

The last issue is her 5-year-old kid. It isn’t so much him, though, as her parenting. She went through an ugly divorce that left her feeling isolated from family and friends. Consequently, she made her child her best friend, and instead of showing discipline when her child demanded it, she let him have his way. He’s gotten whatever he’s wanted, and he’s learned that he can yell, demand things, talk back, and ignore orders because he will inevitably get what he wants. His mother is sweet to a fault: She won’t raise her voice, she won’t punish or curtail bad behavior, and everything he does is a positive. Lately, however, I think he’s becoming too much for her. I get texts all day about his bad behavior breaking her down. When I say I hope he’s being made to experiences consequences, I get a desperate “How?!”’ or explanations that it’s too hard for her to do alone. I feel like as a new boyfriend it isn’t my place to be the disciplinarian, so unfortunately I sit by and watch him run rampant over her on a daily basis. Not only does it frustrate her, but it kills any romantic feelings I may have. Weekend plans get blown to hell, date nights are cut short, romance is replaced with parental duties. Then when I’m no longer in the mood she wonders why.

This is what we’re dealing with. I’m feeling a little smothered, she’s feeling undersexed, and at the center of it all is a devil child no one seems to know what to do with. She’s going through working out custody; soon, she’ll have him weeks on and off and (selfishly) I’m looking forward to it. But until then, she’s frustrated and I’m trying to be delicate about the situation. Is there a way to talk with her about these issues without being insensitive? This is the first relationship I’ve had that I’m genuinely trying to make work, and I’m feeling stuck.


Maybe in Over My Head


You’re definitely in over your head.

Here’s what I love about your situation: You’ve found a woman who’s kind, smart, passionate, and has good intentions and a great career. She also sounds like a natural complement to your personality. You’re introverted, a thinker, an analyzer, maybe a little passive sometimes, but very thoughtful and considerate and measured. She’s more of an emotional person, affectionate and enthusiastic and passionate but also maybe disorganized and scattered and overwhelmed. There are many scenarios where slightly less extreme versions of each of you would hit it off like a house on fire. You’re logical and calm; she’s passionate and affectionate. You’re a calm sea; she’s an exciting storm.

But you are not just your average thinky thinker. You STRONGLY favor thinking over feeling. Time after time in your letter, you told me what you think about the situation, or what you think about how you might (maybe, eventually) feel. You boil down your girlfriend to a list of favorable traits. She has been analyzed by your system and comes back as a Possible Lifelong Partner. We all do this in one way or another, but you are clearly guided by your intellect at the expense of your feelings. You even think that your girlfriend was lying about being an introvert, because you can’t imagine simply feeling like “Yeah, I’m an introvert, too! I love being alone!” and then a few weeks later, feeling like you want your boyfriend around much more often. Feeling one thing and then feeling something else doesn’t make logical sense to you.

I’m going to guess that often, you don’t really know how you feel. You try to solve this problem by considering the facts on the ground, weighing the costs and benefits, trying to come to a solution. I’m going to boldly assert that this will not always serve you well in love. You have to know how you feel. You have to look for passion. When passion isn’t there, you have to notice that, and stay open to what comes next. What would light a fire inside you? I’m not stigmatizing your sex drive here, not remotely. Everyone is different sexually! I’m talking about all of the other stuff. I’m asking you to stay open to a wide range of possibilities, and to try to feel your feelings for a change.

Likewise, your girlfriend is not your average feely feeler. She STRONGLY favors feeling over thinking. When she tells you about her life, she paints herself as the victim of chaotic circumstances unfolding around her: An ugly divorce left her feeling isolated from family and friends. What could she do? She felt isolated! Everything got so ugly! That felt terrible! And now, a bad, out-of-control child has left her feeling frustrated and helpless and unable to discipline him. What can she do? She feels so overwhelmed! He’s so awful sometimes! That feels so painful, you can’t even understand how painful that feels!

Does she ever say, “Whoa, I wasn’t at my best during my divorce. I was so overwhelmed! I really need to reach out to my old friends and mend things if I can”? If so, that’s a good sign. That means she’s self-aware and she wants to grow and maintain ties with lots of people who matter to her. But if she tends to place the blame on everyone else, that would worry me. Likewise, does she say, “Man, I really screwed up by letting this kid think we were equals as a toddler, just because I needed a friend so badly. I really need to draw some boundaries and assert myself more and dish up some serious consequences when he misbehaves!”? If so, that’s good. She wants to shift gears and make some tough choices that will benefit her kid. If she acts like changing anything is flat-out impossible, that’s a pretty big red flag.

Unfortunately, what it sounds like she’s saying to you is this: IT IS TOO HARD FOR ME TO DO THIS ALONE.

So guess who might just end up saving her, because he’s determined that she’s a Viable Life Partner, plus now he’s seriously involved with her and they live next door to each other so it’s the only right thing to do? And guess who is likely to resent saving her when his feelings finally bubble to the surface, because the kid is totally batshit out of control but now HE is the one in charge of disciplining the kid? Guess who’s going to field calls constantly about coming over and disciplining the kid? Guess who’s going to let the girlfriend and the kid move in, because logically speaking, they’re practically living together anyway, and it’ll be much easier to discipline the kid that way, plus doesn’t it seem to follow that things will simmer down once everyone’s under the same roof?

But guess who might just resent being saved, because it makes her feel weak and dependent and that feels bad? Guess who’s likely to start feeling angry because her boyfriend is always in a bad mood and plus he doesn’t ever want to have sex anymore, I mean like NEVER? Guess who’s going to feel like maybe she moved in way too fast — but what else could she do? she needed help! — and her boyfriend is turning into this hardass stepdad out of nowhere, and now suddenly things are so different, all tense and never affectionate, ever! And he never wants to talk anymore! He just shuts down and goes to his room to read a book and the kid goes nuts and what’s she supposed to do about that, when she’s all alone? He says he loves her but he leaves her all alone to deal with everything by herself all the time! He never should’ve moved in, but what could she do? She felt isolated! Everything got so ugly! That felt terrible! She feels so overwhelmed! He’s so awful sometimes! That feels so painful; you can’t even understand how painful that feels!

That’s not the only possible outcome, of course. Maybe you’ll be that very rare couple that walks directly into the fire and faces what you’ve always needed to face, together. Maybe you’ll learn to feel and let go of yourself a little and maybe she’ll learn to take responsibility for herself and her kid and her life. Maybe you’ll both go to therapy and face the goddamn inky-black void of what you don’t understand yet, courageously and boldly, embracing the love and leaning into the madness of being alive and linking your fate to another human being (TWO OTHER HUMAN BEINGS) without hesitation or regret!

Stranger things have happened! People wake up and learn tough lessons all the time. But let’s just state the obvious: You’ve only been dating for a few months. You already have very different sexual appetites, and she already seems to want to see you all the time and seems to want your help with her kid. That doesn’t sound entirely healthy to me.

And not to get too far ahead of ourselves, but take it from me, having a stepchild can be tough even under ideal circumstances. It can be amazing and it can also be incredibly stressful and even heartbreaking. Sometimes you do have to discipline your stepkid. But many other times, you have to be able to turn to your partner and say, “Honey, you need to do something about this. IT CAN’T BE ME.”

So here’s the bottom line: Do not start disciplining this child. Do not become the Boyfriend Next Door Who Tells Me What to Do While My Mom Gets to Keep Being the Good Parent, My Best Buddy, My Personal Doormat. Do not get serious with this woman or move in with her until she can discipline this child. Ask some tough questions (gently, not all at once) about who her friends are, where her friends are, how she plans to make more friends, how she plans to handle her kid, what she would do with her kid at this point if you WEREN’T in the picture, etc. And ask yourself some tough questions about how you feel, too. Are you in love with this woman? Or did you merely say to yourself, “Wow, she is impressive. I could see myself eventually settling down with this very impressive woman, and maybe even feeling real feelings for her, down the road, at some point”? Are you attracted to this very emotional woman because some part of you hopes that she can feel all of the feelings for you?

Listen up, people! Don’t look for someone else to feel all of the feelings for you. Look for someone who makes YOU feel the feelings. And if that seems impossible, then you’ve got to learn how to feel some feelings before you start looking.

You BOTH have a lot of things to learn before you settle into a life together. You both have to take on that challenge INDIVIDUALLY. Not while you’re speeding into a very serious relationship or living in the same apartment. Not while you’re trying to figure out how to raise a kid together. You have to take responsibility for your own separate, distinct emotional challenges, SEPARATELY. You each have to be committed to that. You can’t be committed to it because it seems like a good way to solve a long list of problems, or because I told you to do it and it sounds logical and you think it’s a good plan. You have to FEEL committed to it. And she can’t be committed because that way she’ll win the prize of a man who can take care of everything for her so all she has to do is feel grateful OR complain constantly about how he’s fucking it all up, until it’s too much and she bails. (What could she do? It got ugly! She was so overwhelmed!) She needs to understand the ways she’s currently — actively! — allowing her life to fall to pieces, and she needs to understand that she’s setting herself up to be disappointed all over again, to feel isolated and alone and overwhelmed all over again. These aren’t things you or anyone else can necessarily tell her. She can probably only learn these things in therapy. But she has to recognize the problem and WANT to change first.

I know that sounds pretty dramatic. But the stakes are very high. And look, people are playing house with each other in these same ways all over this great land of ours. Couples everywhere are letting their laziness and passivity and giant blind spots and neediness guide them, every single day. You can see it in their faces: resentment, powerlessness, sexual frustration, blame, contempt. Don’t become one of them! Get your mind and your heart right! Know your feelings. Don’t settle for something that looks good on paper but feels all wrong. Stand up for yourself. Protect yourself.

I want you to feel safe enough to surrender to love completely. I want her to feel that, too. I want true love for both of you, with each other or with other people. I believe that you’re both capable of that. I believe that most of the people out there playing house and fucking everything up and resenting each other for it are fully capable of real, true, collaborative, passionate, soothing love. It’s sad how many people are trapped, isn’t it? But we can ALL set things right. We can! We all deserve to be loved deeply and to love each other deeply.

You deserve it, for sure. But you are in WAY over your head. Whether you work things out with your girlfriend or move on, it’s time to start swimming.


Order the new Ask Polly book, How To Be A Person in the World, here. Got a question for Polly? Email Her advice column will appear here every Wednesday.

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Ask Polly: Should I Date a Single Mom?