How To Date A Single Mom. Or How NOT to…

Dating a single woman can be daunting. Dating a single mom, can be downright terrifying. But, albeit all your other intentions, you’ve met one and you like her. Really like her.

So, let’s assume for the sake of this article that you’ve moved past the novelty of nailing a “milf” (a stupid yet totally relevant word), and have begun to wrap your brain around and perhaps even embraced that this great girl comes with some, er… stuff. (I think “baggage”, no matter the negative connotations it brings, is the term), and you’re okay with the kids, minimal time to herself, baby daddy and most likely an ex that will be in her life forever, part of it all.

Before you proceed, there are some things you need to know,  both to preserve your sanity and ego as well as hers. And also, help you both to build a relationship in which this works. Like, really works.

If you’re questioning my qualifications to be speaking about this. Just so you know, I have been on BOTH sides of this challenging, yet shiny coin. I have been the girlfriend to a man with a baby (and all that goes with THAT). We made it through to the other side, had a couple of children of our own, then decided we were not meant to be together after all and now, 5 years later, I’m a single mother with two kids under the age of 8. Not only that, but I have a circle of single mom friends AND a few really good male friends who are dating, still looking for the one and are finding that a LOT of the best girls they’re meeting out there, have belonged to someone else before and has a kid or two or three (I know one with four. Yikes.) to prove it.

Okay, so you may have dated a lot of women, you may have grown up with sisters or pride yourself in being a gentleman that knows his game. But, I warn you; your usual plan of attack may not work here. What other girls have found themselves swooning over, a single mother may find herself weary of. I implore you to drop all previous learned dating ingenuity and approach her authentically and with unadulterated intentions.

Let’s do this.

1.   Don’t call her after 10.

Granted, she’s probably awake desperately trying to suck out whatever alone time she can salvage from the day, but probably too tired to talk, much less flirt. Unless she’s a drunk, in which case, I would now encourage you to re assess.

However, texting is okay in fact it is encouraged. I know I know…men don’t like to text. But it not only lets her know that she’s on your mind, but let’s her be relaxed and playful in her response. it doesn’t have to be a poem or an emotional vomit. it doesn’t even have to promote a back n’ forth about your day. A simple, “Hope you had a great day! Sleep well!” speaks volumes, keeps you manly yet thoughtful and is just a nice thing to do.

This said, never underestimate the power of a good text. Women are easy prey at night (Don’t yell at me ladies, I don’t mean it like that), but you get the text right and at the right moment, you could find yourself in a surprising, pretty intense round of sexting. Win, win.

I know that texting is not ideal and most men don’t see it as women do, which is a conversational platform. I know that texting has it’s downfalls; misread words, auto text, misinterpreted tone, but it’s important you understand that texting will most likely be a significant part of your relationship with a single mom. Time with her may be scattered and unpredictable, babysitters are expensive, your schedules may leave you unable to see each other for much more than a coffee for weeks at a time. is it ideal? No, but get over it and embrace this new relationship via your fingertips and to avoid any miscommunication, remember “K.I.S.S.” (Keep it Simple Stupid.)

2.  Do not complain about how busy or stressed you are.

I don’t doubt that you ARE busy and stressed. Life is hard. But, unless you have an unusual circumstance; like a big job changing presentation due, your mother passed away or the world has literally fallen onto your shoulders, your busy is nothing compared to her busy. Chances are, she’s got everything going on that you have going on, yet when you’re day ends, her second (maybe third) job begins. Please understand that this is not just a physically draining activity (drop-offs, pick-ups, sports, music, playdates, snack shopping, doctors appointments, lunch packing, dinner making, homework monitoring, bath time and a bedtime routine) that she does in addition to working full time, bettering herself, keeping friendships, keeping in contact with family, working out, putting gas in the car, laundry, dishes and now maintaining you, but is also a total emotional cluster fuck of worries, concerns, guilt, sensitivity and doubt (to name a few), all the while trying to raise human beings to not be total assholes (hopefully). At the risk of playing the martyr, nothing is more annoying then hearing, “Ecch! I’m SO stressed out, I didn’t get to the gym today for a swim and now I’m late to meet my buddies for a drink after work”. We don’t judge you for it. We get it. Your life is different than hours. We’ve made our choices. But, you sound like a pussy.

However, a good single mother will nurture the shit out of you while you’re stressed.

3.  Show interest in her kids.

This can be a fine line; showing too much interest is a red flag. So, when you ask about the kids, make it in relation to her. Ask questions about their personality or who has her eyes. If she tells you a story about one of them, maybe something they said or did at school, listen to her and try to see it through her eyes. No one wants to hear stories about other peoples kids. It’s boring and obnoxious and usually most kids are only cute to their parents, but if you care about this girl, you may find yourself caring about the things that are important to her. Maybe she’s trying to save the Dolphins as well and now you look for information on the slaughter in Taiji. It’s kinda like that. Take interest in the things she loves.

Meeting the kids is another level totally. For me, no one was allowed to meet them unless I felt that this person was here to stay, at least for a long while anyway. Allowing someone to not only enter my children’s lives is huge, but mostly it was about allowing someone to see that part of me, which is as vulnerable as I could get. Meeting the kids can be one of those awkward times. She may feel concerned about what to do with all of you. Do you come over for pizza night and board games? Do you take them mini-golfing or to Chuck E. Cheese? How do you stay who you are to your kids WHILE including someone else? I think that guy should make the move here. Show you care about her by saying, “Id love to meet your kids”, or better yet, “Can I take you and the kids to the arcade and pizza?” I would imagine as a guy, you will wait for her to ask you, but there’s an insecurity there that maybe you don’t want to. If you initiate the meet and greet, it gives her confidence and tells her that you really care and also gives her the opportunity to plan something, talk about it or tell you it’s too soon.

4.  Change your game.

Whatever skill set you have and have used in the first three months of dating a girl I’m sure has worked beautifully in the past. And at first, a single mother will seem vulnerable and privy to your ways. But beware, this will grow old quickly. She has been to your planet and knows your kind. I think it’s fair to say, that a woman with children has some experience with men. I don’t mean in the sack, I mean emotionally. Her time is precious. How much of it she gives to you, is up to her. But, if she finds herself feeling insecure or played or is questioning your intentions, I’m willing to bet, she will walk. Her life is full. She doesn’t have time to evaluate every little thing you say or every text you send and if she does, it will take away from her being present with her kids and she will walk.

On the flip side, for you this may be a breath of fresh air. She may surprise you with how cool she is, how understanding she is knowing how things can come up and plans change. She will be forthright with her intentions, expecting the same from you. Any shadiness or unreliability though puts her in an uncomfortable place and you will lose her. This is not a threat. This is self-preservation and ultimately a mom protecting her cubs.

5.  Beware the Scare tactic.

A single mother may feel inclined to divulge all of her ugly to you right outta the gate. This is not meant to scare you away, its more or less a way to gauge how easily you scare. How into her you are. It’s also a way of putting all her cards out on the table and hoping to find that you hold no poker face, but can handle it all. Can handle her.

Look, no one wants to date someone whose ex is still in the picture. But he is and there may be a time when you meet him. No need to puff out your chest and mark your territory, I can almost guarantee that no matter how great they seem to get along, it is SO over. But, he’s there in her life. Forever. it will be awkward at first and it does get easier, but be sure that this is something you can handle. Because if you were to ever give he the ultimatum of him or you. You will lose. Not because she chose him, but because she chooses her kids. Any good mother should want a decent dad around for their kids.

It’s important you show your strength here. Show her that you are not going to disappear. Show her you love her not in spite of everything she comes with, but because of everything she comes with. Let her know that one of the things you like about her the most is that she IS a mother, I don’t know, lay it on thick. But be careful, you don’t want her to think you harbor some weird mommy issues.

Dating a single mother comes with some challenges for sure. You have to be an incredibly strong person to make it happen. It may be difficult at times, but I promise you; if you’re fortunate enough to find yourself with a single mom and you love her? The respect and love you will receive in return will be one of devotion, kindness, passion and caring. The love you will receive in return, will be like no other love you have ever known.

Photo courtesy of Single Mom Sanctuary.