April 29, 2023
By: Jerry Miller

Dating a Single Mom: Tips for a Successful Relationship

Ahhhh. You found a girl that’s special. She’s kind. She’s funny. She’s grounded. She’s your kind of pretty. Annnnnd she has kids. Wait. Now what? Moms are like superheroes, right? How do you even go about dating a superhero? They are single-handedly making the world a better place one sacrifice at a time. They are master multitaskers and patient providers. They are forced to take one day at a time while also planning for their family’s future. Every single choice they make has an effect on someone else- a smaller, innocent, dependent someone else.

Whew. That’s a heavy load.

Dating a single mom is something that you can’t NOT take seriously. Even if the relationship itself isn’t labeled as “serious.” Things happen, feelings evolve, bonds are formed, and messes can be made if you aren’t careful.

Listen, I know this is all sounding doomy-gloomy but that’s not what I’m trying to convey. I just want you, dear reader, to make good choices and respect her role as a mother before anything else. In short, don’t play around with a single mom. She deserves better and ain't got NO time for games.


Moms are women. Women have desires. And, if she’s open to dating, she has a desire for someone special in her life. If you’re that “someone special” then I have some tips to get you started on the right path.

Be open and honest about your feelings.

First things first, you gotta be honest with yourself about what you are looking for. Are you ready to work toward a lifetime commitment with someone? Or are you looking for a more casual relationship that’s more about having fun and blowing off some steam? Either of those is a fine place to be as long as both people are on the same page. If you are looking for a serious relationship. Tell her. If you aren’t ready to settle down. Tell her. If you are just testing the waters and are open to whatever comes next. Tell her and continue to communicate when/if your intentions evolve. If a single Mom is spending any of her limited amount of free time with you, the right thing to do is to make sure that you aren’t wasting it. Get your intentions out in the open early. Period.

Don’t rush the relationship

Honey, I KNOW it's hard not to dive in head first, especially if you have been single for a while.

Those warm fuzzies and butterflies are addicting! You just can’t rush a relationship when kids are involved, though. Have you ever broken off a relationship with someone and felt terrible for hurting them? Or felt the pain of heartbreak yourself? Now, imagine giving a child that feeling. Terrible, right? Y’all have to protect those babies and their tender little hearts at all costs. Spend a good amount of time getting to know each other deeply before involving the kids. Don’t play house or even come close to taking on a parent role until you are absolutely certain that your relationship is securely in long-term status. The bottom line is don’t become a fixture in their lives until you’re ready to become a permanent one.

Make sure you two are on the same page in regard to wanting more children.

First comes love. Second, comes marriage. Then comes Honey with a baby carriage. But what if Honey’s baby carriage is already full? Maybe she’s kinda happy that the carriage is now vacant and the baby is walking around on their own? Maybe her goal is to make her own basketball team with her body. You don’t know until you ask! She may volunteer this information early herself. But if you are unsure about how she feels and fathering children is important to you, get the “do you want more kids” question out of the way before strong feelings develop. The answer to that question can be a deal breaker for a lot of people.

Lighten her load

Y’all want to know the quickest way into a single mother’s heart? Just make her life a little easier. I’m going to tell you right now, that one of the hottest things a man can do is to take something off my plate, even little stuff. Seriously, 11 years later, I’m still thinking about that time a man came over and saw that I had three remote controls for my tv/cable/DVD player. The dude hopped up and ran to the store with an “I’ll be right back” and no further explanation. He came back with a universal remote and programmed the thing for me. I was stoked! It sounds silly but that small gesture had a lasting effect, obviously.

If you are on your way to her house, ask if you can pick anything up for her. Flowers are great, but a gallon of milk is even better when she forgets to stop at the store on the way home. If she’s having a rough day, offer to order pizza to be delivered. If you’re handy, volunteer to do some minor repairs around the house. Ask if she wants company when she’s running errands alone. There’s a lot you can do if you just pay attention. It doesn’t have to be a big grand gesture to matter, I promise.

The older we get, the more likely it is that we’ll date someone with children. It almost becomes

inevitable, really. It’s not as hard as tv and movies make it out to be, though. If you are already in the habit of considering the needs of others before you think about your own, you’ll do just fine. We’re supposed to be living that way anyways, despite what the rest of the world keeps telling us.

Be upfront with your feelings and wants, take it slow, and go buy that woman her universal remote!

Until next time…

Love y’all and good luck,

Kelly Ann