Tag Archives: hilarious dating snafus as a single mom

Dating a Single Mom: What NOT To Do


So you’ve got your eye on a hot, single mom? Maybe this is new territory for you? Or, perhaps you’ve dated another single mom, so you think you’ve got this down. I’ve got news for you. There is no one-size-fits all model of woman, mother, or single mom for that matter. Just like you don’t want us to make assumptions about you, don’t make assumptions about any of us. I’ve been a full-time single mother for nearly seven years. I have a 7-year-old and a 14-year-old whose father lives abroad. My boys have only met one man in 7 years, as I’m VERY picky about who comes into their lives. I’ve only dated 3 men, all were friends first. With that said, I do go on dates. Over the years, girlfriends have turned to me for advice. The other day, when I was sharing why I broke off a date because he didn’t confirm for Saturday until Friday at 8 p.m.—while also asking me to drive to him—my newly separated girlfriend laughed and said I had high standards. Well, I’ve learned the hard way. If he was someone who thought I was special and cared about how my life works, he would have confirmed earlier, so I could hire a sitter, and then driven to me. (I will likely be spending more money than he will, at $18/hour for a sitter, and shouldn’t be asked to drive 30 minutes each way to see him.)

I’ve learned that saying no to an inconsiderate man, is saying yes to me, and making room for a thoughtful one to come in. My girlfriend made a good point, however. Some men may not be very aware. Even some divorced dads have little idea about the life of a full-time single mom. My Saturday night date that I cancelled, had kids in college, knew I was a single mom, so I assumed he’d be more considerate. But perhaps his ex-wife had done the lion share of parenting? Who knows. And some men, who have never had children, or who share custody of children with an ex nearby, may be good guys, but could benefit from a road map to win the heart of a single mom. Perhaps you are a good guy, who falls in one of the above categories. If so, this is for you.

If you’ve got your eye on a special single mom, DON’T do any of the following:

  • Assume she is desperate and lonely.
  • Always call her the day of—or the night before—to make a date.
  • Assume, since she looks hot in a bikini on the beach, or might have smiled at you while in said bikini, or while working out at the gym, that it’s OK to knock on her door late at night to surprise her with the gift of becoming friends with benefits.
  • Friend her, hang out with her, find out the schedule of when her ex-husband has the kids, and then wait (sometimes months) to ask her out until the day the kids are off with their dad.
  • Ignore her when she has the kids back, and then suddenly appear again when kiddos are gone. This strategy works! She feels how special she is to you.
  • IF she agrees to go out with you for the first time when kids are with their dad, assume she will have sex with you. Go ahead, tell her you love her. Pressure her too.
    (Just don’t be surprised if she gives you a kiss goodbye and waits to see if your ‘love’ lasts until next week, when she has her kids again.)
  • IF you are the lucky man that she actually starts dating on the rare week her kids are with their father, FREAK OUT the following week. Go radio silent and don’t call or text for weeks after the kids return. Assume she’s planning your marriage and father-and-kid nights for you. (Um, NOT Likely.)
  • But maybe you’re ready for those father-and-son nights? Maybe you already know her and her kids, because you were friends first, and you’re ready? Hmmm…Go ahead and Pressure her to let you hang out with the family the week you start dating. She didn’t really mean what she said about not introducing anyone to the kids right away. Right? Not YOU. YOU are different. Therefore, ignore her wishes and show up during the week with pizza and start rough housing with her kids while she’s at the gym or in the shower. How could you hurt her or them, right? Not YOU. What did she say about her ex-husband being a really great guy…until he suddenly wasn’t? She isn’t really scared about starting a relationship. Aren’t all single moms desperate to re-marry? She’ll be fine. Right? (Wrong. Start listening more and stop projecting and assuming.)
  • Disrespect her time with her children. You like her, right? She’s sexy. She’s smart. She’s funny. She must be a strong and caring mother, too. You’re crazy about her. So text her ALL the time. Seriously, who cares if she told you that during the week between 6 p.m. – 8:30 p.m. she focusses on her kids. You’re more important, right? She’d rather talk with YOU and ignore her kids and not continue with her routine, of, what was it anyway? Oh yeah, dinner, homework, bath, book, bed. Who cares about all of that anyway? After a few dates, YOU and YOUR NEEDS are more important.
  • Ask her to text nude pics to you. Text her during the week between 6 p.m. – 8:30 p.m. too, so one of her kids might see your note. That’s HOT.
  • Send her a nude pic, or start sexting. This ALWAYS works—especially during dinnertime, during the school week.
  • Get mad when she doesn’t get back to you right away. Who does she think she is?!
  • Become overly needy, pushy and nagging. She should drop everything, put on a short skirt and heels, hire a sitter, at last notice, and RUSH out to service you! F those kids anyway. Right?! That’s the message you need to send her.

Hopefully, you can’t relate to any of the above. In my humble opinion, there is a huge misconception about dating single moms. The cool thing about dating a strong, independent single mom, is that most of us aren’t clingy. Most of us have our act together. We are focussed on our kids and our careers. We have likely broken away from a destructive or unhealthy relationship and know what we want. We want love, compassion, kindness, a good listener and some FUN. Yes, we like to have fun too—even if we have to plan it ahead of time. If she thinks you are special, she will make time for you. If you ask her to pop out on a Wed. night to go to a concert, that night, and then disrespect her when she can’t go—she isn’t the gal for you. Go date someone 15 years younger without kids…But remember, younger women without children usually WANT to have kids some day. While the independent single mom wants to get to know you slowly without bringing you into the fold of her children—that younger woman may pressure you for more time, marriage and kids before she’s 30. So figure out what you want. And if you want a single mom, tell her why. Why is SHE special? And not because she looks good in a bikini. Tell her what you see in her. She is so busy taking care of her kids, taking care of their needs and raising their self esteem, (and might have an ex who doesn’t appreciate her), that hearing a kind word will make her love for you grow exponentially. Wait for her to let you in. Let it be on her terms. If she lets you in right away, (which I’ve only done once) that doesn’t mean she wants to marry you. She just feels something amazing, instinctually trusts you and sees good in you—and you are a very lucky man. If she needs a few months before introducing you to the kids or before sleeping with you, remember, she’s been hurt. She needs to trust you. If you win her trust and are kind and considerate, she will love you with so much joy and gratitude you will feel like you’ve won the lottery. The independent single mom usually knows what’s important in life: kindness, laughter, compassion, joy. She doesn’t care if you take her to a fancy restaurant. She isn’t demanding. A kind word, a picnic, a back rub and she’s BEYOND happy. She’ll like you for you. She’s very picky. She’s not looking for an exorbitant bank account. She’s looking for something harder to achieve. She’s looking for a good man. She may even inspire you to be a better man.

So, hang in there.  She’s worth it.