How to Date the Single Mom

October 16, 2016

Single moms are some of the strongest and most amazing people you will ever meet, particularly the ones that don’t have the father in the picture.  Why? They show up everyday as mom and dad for their children, the manage a household on their own, they maintain a full-time job, are raising a human alone, pay their own bills, run their own errands and do it all with a smile on their face.  They are completely independent most of the time and still at the end of the day choose to love you and allow you to be apart of their crazy beautiful world.


1. Know she doesn’t need you.The faster you can grasp this, the better. She’s done this on her own and created a strong rhythm of life that revolves around her kid(s)… You haven’t been a part of that, so if you think she needs you, she doesn’t. That may bruise the ego a bit but learn that is a good quality.  I personally have found that this scares most men to death.  But do you really want a woman who sits on her ass and expects you todo it all or a strong woman who can take care of herself and her children.

2. Don’t waste her time. You should know whether or not you have the relational maturity to court a woman with kids. If you are unsure, don’t. Again, she is fine without you and doesn’t need the emotional rollercoaster of you “figuring it out.” There should never need to be a conversation of, “I am really into you but I’m just not sure about the kids.” Don’t you EVER make her feel bad about being a mom or manipulate her into guilt for choosing her kids over you.

3. Don’t know everything about her. While you have probably creeped her profile and know a few things about her and her kids, keep the conversation/questions vague and open. Spitting out details about her life on the first date that you “saw on Facebook” will immediately send a red flag. She’s a single mom, so chances are she watches SVU at night on Netflix and you’ve just fit the profile of every sketch child abductor on the show. Don’t be that guy.

4. Be honest. There is no need to over-inflate her perception of you. There is no reason to tell her how much you love kids if you’re just trying to get laid… Hell, maybe that’s all she wants. We’re all adults here. Be honest. Should you pursue a relationship, it’s going to be complex as hell, so honesty up front is going to create a relationship of honesty.

5. Offer to Pay.  If you’re out and she is paying for a sitter it is really nice if you get the check.  This isn’t necessary, and especially after you have been involved for a while you will likely sort out the who-pays-when conundrum.  But if you tend to take turns picking up the bill, but she sometimes rearranges her life to get out of the house and pays for a babysitter so she can spend time with you, acknowledge that.  More chances than not she won’t let you or expect you to pay because remember she has been doing this alone. But offer!

6. Create opportunities that allow her to be seen. I can tell you that most days, she looks in the mirror and doesn’t see what you see. She’s tired. She’s frustrated. She’s learned to adapt to her reality and the routine has become her identity. Remind her that you see HER… not the mom, the woman. The dreamer. The lover. The companion. The champion.

7. Calm down, no one is asking you to be a dad. The last thing she wants is to jump into that relationship and damage her poor children!  Learning to respect that relationship, know your role, and create healthy boundaries will be of great value to your relationship moving forward, especially with her co-parent. They didn’t work out… cool. She may not especially like him… Cool. Not your business at this point. Her kids may not even like you at first… Don’t take it personally. You’re just not dad, and you’re taking time away from mom.  Someday it’s an option but don’t assume she wants it right away.

8. Trust is going to go in waves. You could build a relationship that is super solid over 6 months and then you’re going to do something that triggers a pain point. She’s been hurt and while she desperately wants to trust you, her idea of a fairy tale has been wounded, and you need to respect that. Patience is your greatest friend, and she’s worth the investment.

9. Once you’re in, you’re in. When she says she loves you, she means it. When she plans a future with you, she means it. When she introduces you to her kids (which you should never pressure), she means it. This doesn’t mean she’s expecting a ring by spring, but it does mean that she’s let you into her heart and her world. If you’re not “in” by this point, you’re a dick for leading her on and not communicating directly.

10. Give her what she needs every day. She doesn’t need your money. She will appreciate the gifts, but she wants your time more than “stuff”. Focused attention. Affirming touch. To be seen. To be heard. To be known. And her kids need to SEE their mother being loved well.

I’m sure I could come up with dozens more, and I’m sure you could add to the list as well…. But this is a good starting point.