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How I Met Your (Single) Mother. And By Met I Mean Married.

So there I was, minding my own business, slowly but surely becoming “that guy” who bounced from one dysfunctional six-month relationship to the next, when I re-met a girl I’d gone to high school with. But not just any girl–a special girl whom I’d always found extremely attractive in so many different ways. I’m speaking, of course, of Caroline.

No problem, right? I mean, “that guy” has been there before, so just dust off a bit of charm and see what happens, right?

Wrong. Because Caroline was a single mom. And given my train-wreck-laden track record in the romance department, I knew I needed a different approach, especially considering there was a little girl involved. One who’d suffered the permanent scar that comes with a broken home.

Nearly a decade later, I’m still sometimes shocked that it all worked out. But it did, and I think one reason is the approach I wound up taking. I’m not saying it’s the right approach for everyone in such a situation, but I am saying that it worked for us. And it started before we ever even went out on a single date.

So, Alli, if you’re reading, here’s the step-by-step breakdown of how I met (then married) your (single) mother.

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  • Consider the Situation 1 of 12
    Consider the Situation
    This might sound elementary, but before you can even begin to forge a relationship with a single mom, you must first give real and careful thought to what it means to be one. If you're looking for a girl who just wants to have fun, I suggest you ring Cindy Lauper. Because being a single mom is far from a carefree situation. Too many people don't appreciate the level of sacrifice that comes with being a single mom. A perspective suitor cannot afford to be one of those people.
    Photo Credit: Flickr
  • Commit to the Concept 2 of 12
    Commit to the Concept
    Once I'd carefully considered and embraced Caroline's situation, it was time for me to commit to the concept. Not to Caroline, but to the concept. This was no easy task for me. I'd dated a couple of single moms before Caroline, but I knew those relationships would never go anywhere because I just couldn't envision myself as a stepdad. But by the time I met Caroline, such a concept didn't seem so farfetched to me, which was a good thing. Because one rule of thumb that I think everyone in my shoes should know is this: if you can't commit to the concept, do everyone a favor and move on along.
    Photo Credit: Flickr
  • Check Yourself at the Door 3 of 12
    Check Yourself at the Door
    Once I'd committed to the concept, I knew it was okay to (try to) court Caroline. Word to the wise, here, and just trust me on this one. If you arrive at a similar conclusion in a similar situation, go ahead and check yourself at the door. Because whatever relationship might ensue will most certainly not be about you. It'll be about them.
    Photo Credit: Flickr
  • Go Slow 4 of 12
    Go Slow
    Which is exactly why I figured I had to go slow. Because it wasn't about me. So, instead of asking Caroline out on a romantic date, I told her (and I quote) "I've decided we should be friends." I know. Lame. But gimme a break. I was doing my best. Plus, it worked. We became…friends. Coming on all hot and heavy to a single mom doesn't make sense for anyone. Especially the child.
    Photo Credit: Flickr
  • Say Hello to the Pink Elephant 5 of 12
    Say Hello to the Pink Elephant
    A divorce is like a death which means that Caroline was in mourning when we first became friends. And what kind of friend would I have been if I didn't offer her an outlet for her grief? So we spent a lot of time talking about her divorce a subject that many might be tempted to try and avoid. But they'd be making a great mistake. For it was through those soulful conversations that Caroline and I first discovered how well we communicate. In fact, Caroline contends that was a big reason why she ended up falling for me. Well, that and the fact that I'm super-hot.
    Photo Credit: Flickr
  • Date the Child 6 of 12
    Date the Child
    Even after Caroline and I realized we had romantic feelings for each other, we still kept things platonic in front of her daughter. But "friends" still do stuff together, right? Which meant that I spent almost as much time with Alli as I did with Caroline. And before I knew it, I'd fallen in love twice. JCO
  • Appreciate the Little Governor 7 of 12
    Appreciate the Little Governor
    That's not to say I never got frustrated during the process of dating a single mom. I did. I mean, there I was in my mid 30s, in a relationship where my interests always took a back seat, as I crawled at a snail's pace and dated a four-year old. But I came to think of Alli as a governor on the engine of a go kart, one that made it impossible for Caroline and me to go too fast. The little Governor demanded a slower pace and I would ultimately realize that it was a healthier one for everyone involved. Even me.
    Photo Credit: JCO
  • Get Real 8 of 12
    Get Real
    Then one day it dawned on me. I wanted to marry Caroline. I'd already committed to the concept so I knew I could do it, but I still had to connect with the reality of what was about to happen.
    Photo Credit: Flickr
  • Expect the Butterflies 9 of 12
    Expect the Butterflies
    Knowing you want to propose is one thing. Proposing is something else entirely. And during the time in between, I was besieged by butterflies, even self doubt. Can I really do this? I'd wonder. Perfectly normal. I'd be worried about someone who didn't get a little freaked out by the prospect of marrying a single mom and becoming a stepdad.
    Photo Credit: Flickr
  • Just Do It 10 of 12
    Just Do It
    Which is why you just gotta do it. Propose, that is. Since the entire relationship had been about so much more than just Caroline and me, I decided to get the Little Governor in on popping the question. She was right beside me when her mom said yes. It's the very first page of the story that is our family.
    Photo Credit: Flickr
  • Marry Them All 11 of 12
    Marry Them All
    On the day we tied the knot, Caroline wasn't the only person to whom I'd made a lifelong commitment. When you marry a single mom, you marry her children, too. That day belonged just as much to Alli as it did to us.
    Photo Credit: JCO
  • Live Hectically Ever After 12 of 12
    Live Hectically Ever After
    So, BOOM. That's it. Piece of cake, right? Now all that remains is to live hectically ever after. No. I'm not saying you're gonna have triplets a year into your marriage. Or, for that matter, a surprise fifth child just a couple years after that. But I am going to say this: no matter how large or small your blended family is, expect chaos. Beautifully unpredictable chaos. But don't worry. No matter how hectic, it'll never be enough to eclipse the memory of the magical journey that began when you met a single mom who eventually became your wife.
    Photo Credit: JCO

Read more of JCO Multiplied:
Dogs vs. Infants
15 Things Every Stepparent Should Know

The 7 Deadly Sins of Fatherhood
8 Reasons Family Road Trips Kill Your Soul Dead
Raising Pretty Girls
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Check out my personal blog over at JohnCaveOsborne(dot)com

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