Dating a single mom might not be the right choice for every single man. It takes a special kind of guy to want to be involved with a woman who is committed to devoting a significant amount of time and attention to her children. But it is also true that a vast majority of single moms, by virtue of having to nurture others, are very unselfish. They engender an amazing capacity to be flexible and compassionate. They know how to make a significant relationship work. So, for the single guy who has found himself drawn to a single mom, here are a few tips to win her heart. 


  1. Plan a family date night. If you’ve met woman who’s a single mom, and you’ve gotten to the place where it is time to meet her children, take the initiative suggest a family date night. The first time you meet her kids should be short, sweet and very kid centric the goal is to endear yourself to her children. For example, invite them all out for ice cream, to the park or for a kid friendly movie. They will be impressed with their mama’s super cool new friend. When I first started dating again, my beau took us all out to Dave and Busters for “our first date.” It was perfect.  Your lady will be incredibly impressed that you’ve come up with the idea. It will ease the kids into getting to know you. On a side note, as much as you would like to kiss her, or hold her hand, refrain. You’ve done a great job of making the kids feel special. Any kind of affection tendered toward their mom in front of them might make the kids feel threatened.  If you both feel a long-term relationship is where you’re headed, you’ll have plenty of private time for love and affection. Ultimately, you want to be a welcome addition to her family not a threatening interloper.
  2. Organize a babysitter. Very often the biggest obstacle for a single mom’s dating life is finding adequate childcare. If it happens that she cannot arrange for her regular babysitter or a family member to stay with her children offer to help her out. Maybe you have a younger sibling who could step in to babysit. You might suggest a trusted member of your office staff or a neighbor you know and trust. Or search out one of the online babysitting services, like or Calm any stranger jitters by allowing your date to talk to the babysitter or arrange a meeting for mom and the babysitter prior to the evening of your date. This kind of single mom assistance will definitely give you “knight in shining armor” brownie points.
  3. Treat her to pamper time. Single moms, especially working single moms, rarely take time out for themselves. Any kind of me-time activity is worth it’s weight in gold.  If you have the wherewith all to take her away for the weekend, without her having to stress about child care worries, (see #2) do it! If it isn’t possible to go away for an extended period of time, or expense is a factor, consider treating your special lady to an hour-long massage, facial or even a simple mani/pedi. It will do her a world of good and make you a superstar in her esteem.
  4. Support her without stepping on her toes. Although it may be challenging to not express your thoughts and opinions about how she raises her children, do your best to try and not mix in. This may be especially challenging if you are single dad and you have a particular standard for how you raise your children.  Regardless, it is not your place to insinuate your child rearing methodology or to reprimand her kids. The only exception might be, If and when, your beloved asks for your help or input. In that case you both may want to discuss your child rearing privately. Then allow the mom to incorporate your ideas into her child rearing style. Kids will always be more willing to accept input from their biological parents rather than a boyfriend. It’s best to keep your relationship with her kids as even keel and non-confrontational as possible.
  5. Know her kids come first. Finally, the most important tip I can share with any man who is seeking the companionship of a single mom is to understand that her kids come first. This can frequently be a deal breaker for many relationships, but it doesn’t have to be. As an independent and compassionate man you understand that she’s brought these children into the world and feels responsible for their welfare 24/7. Verbalize this to her and it will be gratefully received. Also keep in mind that a woman’s need to be a dedicated mother does not mean she can’t be a loving companion. She can. Single moms have an amazing capacity for sharing ALL their love.

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2 Comments on This Post

  1. Amy

    Thank you Kerri and The Agency. I’m a single mom and I love those ideas:)

    January 28, 2014 Reply
    • The Agency, An Exclusive Matchmaking Experience

      Thanks so much for following Amy!

      March 12, 2014 Reply

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