Dating a single mother


After 17 years of being out of the dating scene, I have decided to start my life anew. I got divorced almost 10 years ago and received a decree of nullity 3 years ago. Also, she is Catholic and free to marry.

Recently I have started going out with a single mother, she is in her early thirties and I am in my mid-thirties. She has two children, 9 and 7; while my three children are teenagers. We have gone out four times already and have enjoyed each other’s company.

I realize that dating a single mother is going to be more challenging than dating a single woman with no children, especially when it comes to going out since her children will always take precedence over any of our planned outings. I also realize that if we were to develop a relationship it would be slower to attain because of our responsibilities. I am freer to go out since two of my children live with their mother, while the eldest lives with me and he is 17.
I’ve been doing a lot of reading online about dating and whatnot, but it seems as if most of the information I find is more geared toward single persons with no children. For example, on several blogs I read that if a woman cancels your date, then she should take the initiative to schedule the next one. Again, to me this seems geared toward persons with no immediate responsibilities.

Just getting back into the dating game has been strange, awkward and feel like a newbie all over again. Any guidance will be helpful!


The advice about who cancels and who reschedules is frankly silly.

The basis of a good relationship is friendship. Be her friend. Within the bounds of chastity, don’t get hung up on someone’s rules and keeping score (who cancelled when and why) is no way to begin a relationship.

At their ages, the kids don’t need to get attached to you if this is “casual”. If you both are considering marriage, then, define what your relationship with the kids is going to be.

Is dad in the picture at all? Is that relationship acrimonious or is it civil on her part?


Follow what works for you both. If advice you’re reading doesn’t fit, then don’t apply it. Keep in mind your children, and wait until you both think there’s a serious future ahead of you until introducing them. Be confident and have fun.


I thought that those rules were silly as well. I want to develop a strong friendship with her first before taking a next step. The children haven’t been introduced in our relationship at all and I do not think that this will happen any time soon either. I am not pushing her into a courtship either and want to earn her trust. The father is still involved in their kids’ lives and from what she has told me, they keep it civil.


It sounds to me like you’re on the right track. Taking it slow and developing a solid friendship are the best things to do.


I think you’ve got it all worked out :smiley:


Don’t go by online gamesmanship blogs. You are mature, adult people. Just believe the best of her, communicate openly, and be honest and respectful.

Stay away from Internet dating advice, just use common sense and go with your gut.


I married a single father. I had never been married; he was divorced (received a declaration of nullity and we are sacramentally married).

We didn’t worry about cancelling and rescheduling. Many of our “dates” consisted of Hubby and DSD coming to mine or me going over to his, especially once DSD started Grade 1. (Hubby and I lived an hour’s drive apart and DSD had school in the morning, so she couldn’t stay up late.) Hubby introduced me to DSD about a month after we started dating in person. Prior to that we had met online and been corresponding for 4 months before our first meeting in person. Many times we would all go to Mass together and go out to dinner or go back to my or Hubby’s place and have dinner together. We went grocery shopping as a family. We did things together, all three of us. Our relationship grew organically by spending time together, even doing just the mundane things.


I’ve dated single mothers. Topics I look at in the process of getting to know her: her and her children’s relationship to the ex. Is it civil or not? Then I will eventually want to know about the issues that caused the divorce. Then I will want to know how well she balances her priority for her children with her relationship to me. Then I will want to know about her willingness to have one or more children with me.

Some single mothers are good to excellent candidates for remarriage to another man. I’ve met a few. Some are not. I’ve met those too. Nothing wrong with dating them, they are part of the pool of available women in my age range, and if their marriage was annulled, then they’re just as eligible as the never married. But their motherhood does add considerations that aren’t present with childless women and they do have to be thought through.


Yes! You should be reading and trying to understand her instead of the dating blogs. I’ve decided that most of these dating rules are nonsense—everyone is different. I would recommend you not be afraid to talk to her about the kids and be assertive with your feelings on that. While I think it’s important to respect her boundaries as a mom, it’s also important to expect her to make you a reasonable priority. I would discuss with her future parenting team roles if you are to get serious. For instance, I would discuss with her whether she would have her kid’s preferences come before yours and how/if she would want you to behave as a parent to her children. I used to think it was important to wait to introduce the kids, but now I think it’s perfectly healthy to introduce kids to friends you are dating in a very casual, unintimidating way, much like you would do with a platonic friend. I think it’s important to gage that dynamic between the potential partner and the kids early on. I remember I invited a male friend over to my house to give me a hand with a home project. It was a great opportunity for everyone to gage the situation in a non-threatening way. But I do think it’s inappropriate to encourage a relationship between the child and the potential partner at any time during the dating period.


And don’t forget, she is also dealing with the challenges of dating a single father. Good luck!


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