How To Date A Single Mom

Recently, I was asked an interesting question by a single, mid-40s, childless guy:

“How do I get a copy of the manual for dating women with children?”

Ahhh, the elusive guidebook to (successfully and happily) dating a single mom. I don’t actually have a copy of the manual in question but, having had nearly three years of experience in the role of single mother and a couple of dating relationships under my belt, I do have a few ideas on the subject.

I’ve always believed that single mothers give heroic parts of themselves to give their children good homes. But it wasn’t until I became a single mom that I realized how genuinely difficult the task was and how draining it can be, every day and every hour. There are many, many times when I’ve thrown up my hands and said, quite emphatically, “I’m not dating until Ben is 10 years old! No, fifteen! It’s not worth it. I can’t do it!”

However. I do think that it is important for single parents and especially for single mothers, to date. Single mothers are notorious for giving, giving, giving and don’t take much in return. Dating allows a single mom to slip out of her everyday roles, even for a brief evening, and to cultivate an identity that does not involve racing out the door at 8am while barking orders and grabbing at backpacks, lunch boxes, and permission slips. In the company of an adult male, a single mom might momentarily forget the guilt she feels over working too much and the stresses of financial matters. For a few short hours she will not have to issue a time-out, she will (hopefully) not have to clean up poop and she can actually share a meal with another person who does not demand her to be a short-order cook, dishwasher and kitchen manager, all at the same time.

If you’re still reading, even after that last sentence, you must really want to make the relationship work with a single mother. So, here’s how to do it:

Don’t be fake

Don’t feign interest in a single mom, just so that you can have a fling. I can see through this ruse more clearly and quickly than you’ll ever imagine. Having a 5-year-old male means that my “BS meter” is constantly on high alert and I am perceptive enough to know when I am being duped. Be genuine and sincere, be yourself, and I will welcome the opportunity to spend time with you. A man who is sincere and shows genuine interest with no ulterior motive is any girl’s dream whether she is a single mom or not.

Don’t be fake, part two

You can’t just be genuine with the mom, you also have to be genuine with her child. If it does get to the point where you meet Ben, be yourself. Kids are almost always smarter than parents and will know when someone is being fake with them. Be nice, show genuine interest (anything involving Hot Wheels is a sure fire way to get my son’s attention), and soon you will find that your efforts are reciprocated in spades.

Honor thy single mother’s bedtime

I have a bedtime and so does every other single mother that I know. We have to: it’s called survival. On a good day, my son will sleep until 6:30am; on a normal day, it’s more like 6am. That doesn’t leave a lot of leeway for me to be up late. Not that I want to be. After 14 hours of parenting, working, and juggling the many other tasks in my daily life, I have no interest in seeing anything past 10:00pm on the face of the clock. There are very few events that will entice me to stay up late. I’ve found that, on a work night or a “Ben” night, it’s just not worth it. A rested version of me is much more happy, sane and even-keeled than the tired version. It’s okay if you’re a night owl; just don’t expect me to become one.

Romance her (a little)

You don’t need to be a single mom to appreciate a little bit of romance, but the single mom will definitely appreciate the romantic attention you provide. For me, this doesn’t mean flowers or jewelry. But a sweet text or an email saying that you are thinking of me, or even just checking in to see how the Ben’s doctor appointment went or how my work day is going, will go a long way.

Be flexible

Flexibility is key when dating a single mom because she is always juggling a lot at once and has no one to share her responsibilities with. I may be certain on one day that I can make plans with you, but then have to cancel at the last minute if my ex gets called to work, if Ben has a long and sleepless night (which happens way more than I’d like), or if my mother is too tired to babysit. Be understanding of these scenarios. Don’t sulk. Re-group and try again.

Consider your own plans for the future

Unless I specifically say that I’m looking for something open-ended or casual (which would be highly unlikely), carefully give some thought as to whether you want to have a stepchild. Or not. Daunting? Yes. Realistic? You bet. Consider whether you even like kids. Not everyone wants to be a parent and being childfree is a valid choice, but you can’t have your cake and eat it too. The single mom comes with kids. Obviously. You might be able to avoid interacting with them or even seeing them for several months but that won’t last forever.

Be open-minded

You may not have ever envisioned yourself becoming involved with a single mom, but the right situation (and woman) can change your perspective greatly. Single mothers bring the blessings that come with loving and being loved by a child, and that’s an amazing experience.

Understand that her priorities are very different from yours

A single mom battles daily with unending priorities. She may not even be sure which ones are at the top all of the time because they all seem mission critical to her. That doesn’t mean that you aren’t a priority, but her priorities may shift on different days just depending on how the day goes. Some days you may find yourself wondering where you fall on her priority list, and this is where flexibility and communication come in.

Here’s what I have to say on priorities: If I’m including you in my life, then I want you to be in my life. Simple as that. Be flexible and communicate often, and I will find many ways to show you just how big a priority you are to me.

Be considerate of her time

The single mom is generally torn between her kids, her work, her family obligations, her social life, and a million other responsibilities that she has no one to share with. Given this, it’s a good idea to be a little considerate of the time in which she has to do all of those things. Case in point: If you call me up on a Saturday afternoon for a date that night, it is very likely I will turn you down. This will be no reflection on you, but more likely a matter of me simply having a 5-year-old who is counting on dinner and bedtime with his Mommy. It’s always a good idea to find out when my ex and Ben have vacation plans (which is quite frequent, I might add) and you can be a step ahead planning anything with me.

Offer to help

If I’m having an overwhelming day (which happens in my world more than I’d like to admit), it’s nice to have someone who steps up and offers to do something to lessen the load. It doesn’t have to be a grand gesture of babysitting for hours on end while I take a spa day (although I would never say no to that) but can be as easy and as sweet as offering to read Ben a story before bed so that I can catch up on client calls.

Expect to have “The Talk” early on

Many men balk at The Talk in any relationship, even if they want the relationship to have some longevity. The Talk doesn’t mean that I want to push some guy to commit to a lifetime with me. Quite the contrary. I’ve found that The Talk is a great way to discover what page everyone is on. To be blunt, I don’t want to waste the time that I could spend with Ben on a guy who may or may not be into me for the long-term. It’s always okay if we want different things, and it’s okay to want something casual. Just be sure that I know that.

Understand that a single mom will be sad sometimes

When my son goes off to his dad’s, I’m always sad. The sadness is fleeting and it generally only lasts for a few moments each day but it’s something that I’ve learned to recognize as a normal part of a single mom’s attachment to her children. Very few of us single mothers got married and started a family with the idea that at some point, we would have to give up 50% of our time with our children. That’s a bitter pill to swallow and it’s a lot of time to miss out on. Expect a single mom to be a little blue now and then, especially around the holidays. It’s not “Prozac sad” but there’s definitely a sense of melancholy that can drift into and out of a single mom’s day without reason and certainly without notice.

You will, at some point, have to be involved with the children

Most single moms and single dads are hesitant to take this step until everyone is certain that the relationship has some staying power. Hesitancy is good in this case and should be honored. When the time is right, treat the occasion delicately, and treat it with the respect and appreciation it deserves. The first-time meeting WILL be nerve-wracking for you, and it will be for me as well, but I would not have you meet Ben if I didn’t want you to be part of our future.

It happens: The kids might not like you

Unlike dogs and kids, boyfriends, girlfriends and children don’t always mix well. Kids can be resistant, they can be jealous, they will be uncertain and they can be nasty. This has happened to me and it’s not fun. I always say that there is a window of time to capitalize on the innocence of children in this situation and it generally occurs between the age of two and six. In fact, it’s been my experience that you’re pretty much golden during these years because kids in this age bracket, by and large, welcome any new stranger into their lives with open arms and open hearts. Believe me, my son has been in love with every girl that my ex has dated and he has been equally accepting (if not less effusive) to the men that I’ve introduced him to (just two).

I think at some point, children realize that you are a threat to their mom’s time, you are a threat to their relationship with their dad, or you are just simply a threat that they don’t welcome. Let Mom handle this one. If this relationship has longevity, she will work on them. Keep being genuine, but most of all, have patience. With time, those kids will learn exactly why mom is so crazy about you. Hey, you got this far, didn’t you? Don’t back out now.

Know that you are likely getting a real prize

If you are considering a relationship with a single mom, it may seem at first like you are taking on more baggage than all the lost luggage claims that United processes in a day. It doesn’t have to be this way, and don’t go in thinking that. Single mothers are among the most mature, responsible, and loving people on the planet. They are always juggling something, but are adept and even good at slowing down the pace to sweep up a crying child and provide nurturing or to gather everyone together for a healthy meal and create some semblance of family and routine. Go in open-minded, patient, understanding, and most importantly, sincere. If this relationship is meant to be, the rest will fall into place.