Dating…with Children PART 2: The Childless Other Person

So, you’re smitten with a parent…but half of those kids’ chromosomes are not from you. Yikes.


Not yikes! Shame on you! We’re awesome!

OK, no shame, really. It’s totally acceptable. In my opinion, any aversion to dating a single parent is just as superficial as being primarily attracted to a certain skin color or body type. And the stigma of single parenthood is just as archaic as Jim Crow laws. Unfortunately, the philosophies still prevail today; they simply lurk under different headings  <ahem bathroom & gender ahem> [don’t get me started]  or are introduced with false acceptance such as, I’m fine with it, BUT...

Save your big but.

Abstaining from single parents is simply your preference. It’s also something you can get over – if you want to. But the cool thing about dating is that you get to date who you want. So if you’re likely to avoid dating a parent, that’s OK. This article is not for you. You can also jump onto chats like these and connect with your fellow brethren.

Ok ok ok, maybe I’m a little bitter. But still. I’ve been burned. I’ll venture to average about 90% of men I’ve dated since my divorce that either went ghost or ended things because I’m a mom have come back, regretting their judgmental rush to rule me out. Well, as I’ve said before: 1. I’m awesome (along with many other single parents) and 2. I will not be back-burnered while you look for something better. Because when you come back feeling silly and want another try, this is what I’ll say: Nope.

And I might sing this song.

And I might make this face.


On the other hand, if you are brave enough to think about entering into a relationship with a single parent or if you are already in a relationship with a single parent, here are some things to consider:

  1. It’s OK to say you’re not ready. So, yes, you are head over heels for a single parent. Praise Baby J. But you’re terrified to meet the kids. What if they don’t like you? What if you don’t like them? What if they’re naughtier than you expected? What if xn?

Remember, you have a voice. If things are moving too fast for you, just speak up. Slow does not mean no. No means no. Asking to slow down isn’t rude or rejecting; it’s valid and healthy – especially for the kids. The same way kids deserve two happy and healthy parents, they deserve the happiest and healthiest version of YOU as the significant other. If you’re really with your Best Match, they’ll understand and respect your pace.

Asking to slow down isn’t rude or rejecting; it’s valid and healthy – especially for the kids.

  1. Acknowledge what you’re in for. I’m reading this incredible book right now called Everybody’s Normal Till You Get to Know Them by John Ortnberg. A section in the very beginning stood out to me and will stay with me forever:

A friend of mine was ordering breakfast during a recent trip in the South. He saw grits on the menu, and being a Dutchman who spent most of his life in Michigan, he had never been very clear on the nature of this item. So he asked the waitress, “What exactly is a grit?”

Her response was a classic. “Honey,” she said (in the South, waitresses are required by law to address all customers as “honey”), “Honey, they don’t come by themselves.”

Grits don’t exist in isolation. No grit is an island, entire unto itself. Every grit is a part of the mainland, a piece of the whole. You can’t order a single grit. They’re a package deal.

“Call it a clan, call it a tribe, call it a network, call it a family,” says Jane Howard. “Whatever you call it, whoever you are, you need one.” It is not good for man to be alone. Dallas Willard says, “The natural condition of life for human beings is reciprocal rootedness in others.” Honey, you don’t come by yourself.


None of us come by ourselves. Even if you’re an anti-single-parent dater, you still have to deal with your lover’s mother(s), father(s), sisters, brothers, grandparents, aunts, uncles, godparents, cousins, best friends, work friends, kinda-friends, dogs, cats, lizards, fish…germs. Everyone comes with an arsenal of people and connections and microorganisms that you’re going to have to navigate anyway. So kids aren’t going to be that much more added to the circus for which you’ve already bought non-refundable tickets.

Kids are a lot of work. They’re needy. They’re loud. They’re rude. They’re dirty. They’re messy. But they’re also hilarious. Compassionate. Honest. Adorable. Gentle. Affectionate. And they’ll teach you more about life than any fancy professor with a ton of letters after their name. You’ll feel drained, overwhelmed, terrified, uncertain, and you’ll probably doubt your decision at least three times a day.

But children are, unfortunately (or fortunately?), temporary; just like any season, phase, and quite frankly, all of life. So enjoy the ride. Savor the moments. Take pictures. Smell the rain. Remember how tiny their hands are in yours. Remember how soft their fingertips are as they touch your face. Remember that joyful giggle.

As I mentioned in PART 1, the kids will grow up, move out, chase their own dreams and start their own families. At the end of the day, you’ve just completed one of the grandest adventures with your Best Match and Life Partner. Isn’t it amazing what you two can accomplish together? It will be worth it.

Remember how tiny their hands are in yours. Remember how soft their fingertips are as they touch your face. Remember that joyful giggle.

  1. Remember what we’re NOT. Single parents are not charity cases. We don’t want your pity. We don’t want favors. We are strong, resilient and dedicated. We are fierce and driven. We’re survivors. We don’t need you to be our hero because we’ve already become our own heroes –for ourselves and for our children. Please don’t date us thinking we need you or that karma is going to come rain goodies on you because you’ve taken in what others have kicked out. Remember that we’re just souls hoping for passionate unconditional human love like any other single person. If you think you’re doing some noble deed by dating a single parent, please leave us alone.

Remember that we’re just souls hoping for passionate unconditional human love like any other single person.

  1. Know your role and know your value. You are engaging in a partnership with someone that could be – or is – your Best Match. Your role in their life and family is their Best Match. You are not a substitute parent (and PLEASE don’t even entertain the temptation to compete with or one-up the other parent). You are not a babysitter. You are not a disciplinarian. If you feel a lot of pressure to fill roles outside of significant other, speak up. Of course, joining in a lasting partnership involves sharing some responsibilities, but take a step back and consider how your presence lands in the kids’ world. It’s better to slow down and limit your time with the kids than to impose and confuse them. Remember that your presence might make them feel guilty; like they’re cheating on their other parent by enjoying your company. More on the kids point of view in Part 3…

Your role to the children varies, depending on their age and developmental stage when you enter the scene, but you are always meaningful. As your relationship with the kids grows, you can be a huge asset – especially to older children. For teens in particular, you might be their preferred adult confidant and listening ear; they might open up to you more than they would their biological parent, trusting that you will guide them without shaming them. You can be a very powerful positive influence for them when they need a consistent and reliable presence the most; something really meaningful, filling a unique space between friend and parent.

Joining in a lasting partnership involves sharing some responsibilities, but take a step back and consider how your presence lands in the kids’ world.

  1. Communicate – comfort level and expectations. I personally hold to the One Year Rule. When you have kids and you’re dissolving a marriage in the state of Illinois, you’re required to take an online course and pass an exam on successful co-parenting. It was actually very practical! (High Five, State of IL!) When it comes to significant others, the course recommends the One Year Rule; that you and your significant other have been consistently and officially dating for at least one year before making introductions to the kids. This is to protect the children – from confusion, from having too many inconsistent people coming in and out of their home, from getting attached and then getting heartbroken when you break up, from setting their relationship norm to a standard of “shallow” and “temporary,” and so forth.

If one year is too long – or not long enough – speak up. As I mentioned in another article on starting a relationship off right, holding back your fears or reservations only plants seeds of resentment. Communication is the foundation to any relationship, no matter how intimate or minuscule. So speak up. Discuss. If you’re not comfortable sleeping over, say so. If you don’t want to watch the kids, don’t. If you’re not ready to be alone with the children, let it be known! Your successful and loving relationship with your significant other’s kids revolves around you being comfortable enough to be your Best Self. Those adorable kids deserve to receive the best version of you when you’re together.

At the end of the day, you’ve just completed one of the grandest adventures with your Best Match and Life Partner. Isn’t it amazing what you two can accomplish together?

So talk about the big things with your partner and check in to make sure you’re still on the same page. Coordinate schedules, make sure you have date nights, make sure your interactions with the kiddies are balanced – neither imposing nor scant – and if the other parent is in the picture, you’d better figure out how to cooperate with them, too! Grits, man. Amirite?


Check back soon for PART 3: The Kids.


why do men go crazy around the holidays part I

is it just me or do single men go insane this time of year?

it can’t just be me noticing this and I’m going to talk about it in my next webisode. I have my own stories.. what are some of yours?

Can’t wait to hear more and try to figure these beautiful creatures out…

email me here:

or message me on fb here:


so, what, then, is a serious relationship?

Yes, I finally heard from Sir Crickets… the one that left me high and dry after I confessed my readiness to take the next step.

Now in all truth, I didn’t confess like a normal adult. This is my first big step since my divorce and I turned into a Disney princes as soon as I realized we needed to DTR. I pulled away from him and said, “OMIGODILIKEYOUSOMUCHANDICANTDOTHISANYMOREWHATAREWEDOINGGGGGG?” and I literally ran away.

Quite literally. Had I been in glass slippers, I would have left one right in the middle of Chicago Ave.

And I haven’t seen him since.

((please feel free to laugh))

I sent him an email and several texts the next day apologizing for acting like a teenager, and ultimately asked to just talk like normal people.

*Cue the weeks of silence.

I exposed my heart. I made myself emotionally vulnerable. And it backfired. I don’t do it often. And man does it sting when I do…

Here’s the deal with me. I keep most people on the superficial level. I’m fantastic with first impressions. I impress people. And then I sneak away alone at the end of the night. On purpose.

I’m very selective about who gets in. Into the real me. Mostly because I’ve been the token, I’ve been excluded, I’ve been rejected for a significant part of my life.

The majority of my relationship with my father was the recurring empty promise of him visiting for birthdays, concerts, recitals. Never showed.

Crushed expectations.

In fourth grade I had a birthday party at a roller rink. I invited my class. I invited the third graders. And I invited the fifth graders. And I sat there for an hour on my birthday in an empty party room, waiting for everyone to show up. And no one did. Not one. I was in denial until I overheard the event planner tell my mom she could have a full refund. The woman walked over to me and gave me a pathetic poor puppy look and a balloon. I just stared at her.

Crushed expectations.

From that moment, I maintained my outward bubbly personality. I kept face. But on the inside I gave a big EFFYOU to the world. I like being busy. I deliberately spread myself thin. I join as many groups as possible. That way, if there’s a party I don’t get invited to, I’m not hurt. Hey, it’s cool – I didn’t know them like that anyway.

I’m slow to trust. Very slow. But once you’re in, you’re in. And when I love, I love hard. You can’t make me not love you anymore. I’m a beast like that.

In fact, I think it’s incredibly curious that Urban Dictionary has me figured out so well…


Female, sexual appeal that may be difficult for her to embrace, leaving her with an awkward approach. Likes stability and feeling safe. Loyal and committed to the ones she loves. Passive aggressive. Loner at times. Tendency to be a hermit. Loves to be acknowledged. Curious about her purpose. Religious at heart, stubborn. Slow to trust but quick to love.

Octavia will stay with the one she loves even though she questions her choice and trust for him. She is the type to break up or stop a fight before it takes flight. Her insecurities may lead her to come across as awkward because she’s self-conscious


It actually is kinda creepy.

But I digress. Sir Crickets.

He says, “I had stopped considering you would be interested in something serious quite a while ago and my brain doesn’t really move backwards.”


So two months of a pattern that would suggest we were leaning towards something serious turns out to be a complete farce.

“I thought we were just having fun,” he said.

I was so confused, I actually had to write a poem about it. I normally don’t like poetry. Yet somehow, when I’m really aching, poetry just does it for me. Very cathartic. Check it out:


You said I was amazing.

You said I could have a key.

You said you wanted me for my errrrythang.

You said you didn’t want to share me.

You said I felt like heaven.

You said I looked like an angel.

You said it was cute when we randomly matched.

You said I was the only one that orders steak properly.

You said your bed was too big without me.

You said we were kindred spirits.

You said we were the same person.

You said I made your heart grow two sizes bigger.

You said.

You said.

And when I said I’m ready…

You said nothing.

So then, what is a relationship?

Now, for the rest of this story, I leave Sir Crickets alone. In all honesty, I’m not here to bash him. I’m not now and never have been mad at him. Not my style. I think he’s a marvelous person and would love to see him again some day.

But what, then, is a serious adult relationship?

A relationship is a thing.

It is a seed.

Aight yall im boutta preach. PRAYCH! (Matthew 13)


This is also partially inspired by the sermon I heard at church Sunday: Whaddup Soul City Chicago!

The soil cannot sow its own seed. The seed must be carefully placed by a loving hand.


Yeah. Heard?


The seed is not the attraction, chemistry, passion, likes, dislikes, similarities, experiences, jokes, scars, memories—this is the soil. Two people that can’t keep their hands off each other and can’t stop giggling when in the same room: the soil.

But the seed…The seed is the deliberate decision to turn all those fantastic emotions into something strong, healthy and lasting. You can have good soil with hundreds of people. But that seed. That seed is special. It’s not a feeling. It’s not an emotion. It’s not sex. It’s not a child. It’s a decision.

When do relationships fail? When there is no decision. When two people are just kind of letting things happen. Or when someone stops cultivating it.

I know, I hate those DTR talks just as much as the next dude. But are we really just each other’s’ play things? Is that what all this is? Are we all just toys here for each other’s physical and emotional pleasure? Or is the physical pleasure one of the perks to searching out that one person you want to invest in? What makes someone worth the try?

For me, dating is like an audition. Or a sales call. Or a job interview. It’s not just about having directionless fun with a person over the course of several weeks or months just because you need someone to hook up with.

((To be honest, this is probably why some arranged marriages work; they decide to make them work.))

If you already know you’re not going to plant the seed, move on. Plenty of fish. I can get good soil anywhere. Mmmhmmm dat good dirt, baby.

And if I know I don’t want to make a decision with you, I’ll go find the next soil. Simple.

Now, back to Sir Crickets. Where did we fail? For me, I was slowly advancing him to the last interview, whereas I had lost the job a month or more beforehand and I never got the memo.
I got straight up played yall.

*Cue Taylor Swift – Blank Space

And The Good Pastor? Well, let’s just say we planted the seed…but as it grew, what I thought would be a pumpkin, turned out to be an apple. We were growing two different things. Talk about crushed expectations.

Before this horticultural metaphor gets too out of control, here’s, the moral of the story:

A serious relationship is a decision. Not a feeling. It’s not something you lose. It’s not something that fades. It’s a deliberate decision to give each other a shot at something more.


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