Advice For Guy Dating a Woman With a Young Son


dating a woman with a young son



I am dating a woman with a young son. She is amazing, but sometimes I feel suffocated. I’m not sure I should stay in this relationship. We are both very young—24 and 26 and I’m not ready to be a father. I don’t even have a job yet.


Wow. I forgot how hard dating in your twenties can be! You are so young and you have so much ahead of you. I am happy that you are being honest with yourself, and are not blinded by love, which can lead to a commitment (marriage) that clearly doesn’t feel right for you.


If you are asking for my advice, here it is. I only learned this later in life. Love is pretty simple. And when something feels really right, you will know. Because when you love someone, in order to be truly happy you have to love and accept everything (and everyone) that comes with that person. I’m not saying you don’t love her child—I have no idea how you feel about him. But, “I’m not ready to be a father” to me means that you things don’t feel right. Isn’t “I feel suffocated” telling you maybe the relationship isn’t working?


Loving all of someone means loving everything that comes with her. That could be everything from her faults, physical illness, her nutty family, her baggage, and yes, her children.


I’m not telling you to end things with this woman who you call “amazing.” That is no small thing, and there are obviously lots of reasons you love her. But, you owe it to her and to yourself to do three things.


  1. Trust your gut and be honest with yourself about what you want. Really consider everything before you get even more serious. Decide what this woman and her child really mean to you.
  2. Be upfront with her and let her know how you feel. Don’t necessarily break up, but if she is expecting that the two of you are going to be engaged soon, doesn’t she deserve to know it’s not happening? You should be straight with her about what you are thinking. What she decides to do at that point is up to her.
  3. Focus on getting a job. At 26, you should be figuring out what makes you happy professionally and how you are going to support yourself and possibly your future family. Finding a job that makes you happy isn’t easy. I get it. But, there is nothing like getting immense gratification from your professional life. It changes the way you feel about yourself and about your love life. Trust me, I know about these things. I’ve had jobs that I hated so much I cried every day, and I’ve had jobs I loved so much I couldn’t wait for Monday morning to come. I’ve failed at many things but I’ve succeeded at many things, too. All I can say is, work can be so truly fulfilling and rewarding, that your love life just kind of falls into place. 


Dating a woman with a young son is wonderful, and I have this feeling that maybe at the beginning, the attraction was to protect her, rescue her, rescue the son, be the good guy, the Prince Charming. While that is great if it feels right, that road is very difficult and takes a guy who really really wants it. Honestly, I don’t think that’s you.


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Jackie Pilossoph

Editor-in-chief: Jackie Pilossoph

Divorced Guy Grinning is a blog for men facing divorce and dating after divorce. It's kind of like hanging out with your platonic female divorced friend and hearing her perspective on your divorce and your love life issues.

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