If my affinity for the male “species” didn’t start at birth, it began soon thereafter. My mother loves to tell childhood stories about it.

While my sisters cried like banshees whenever my mom left the house, I pitched a fit until my father took me along with him to construction sites, my building blocks in tow.

While my sisters joined my mother and other visiting wives in the kitchen during football season, I plunked myself down in the middle of the living room with the men, watched the games, and “sneaked” sips of my dad’s Budweiser.

On one occasion, I crawled up into the lap of my oldest sister’s high-school boyfriend (he was 15 years older), pointed to the peach fuzz that lined his upper lip, and declared:

“My mommy has one of those.”

I’m not sure whose face got redder after my mustache comment: my mother’s or his.

Beyond the Stereotypes
If you’re the labeling kind, you might choose the word tomboy to describe me, but you’d be wrong.

Yes, I enjoyed many traditionally male activities, but I participated in them wearing flowered dresses and ribbon-tied pig tails. Strawberry Shortcake rocked my world – in fact, she metaphorically vomited all over my adolescent bedroom.

This dichotomy of prissy vs. masculine continued from preschool to college. I cultivated amazing friendships with girlfriends, but I always gravitated to hanging with the boys (see Falling in Love at 4 Year’s Old).

Thankfully, they didn’t rebuff me, and some of my best friends became guy friends over the years.

Then I hit my 30s and my experience with the opposite sex transformed into a “curse of the naive.”

Case-in-Point #1
After spending an evening with my long-time friend Leah, her husband and several of their friends, I found myself and one of the other older (an understatement) gentleman (a misnomer) as the last folks standing. Both he and I hadn’t quite finished our drinks and were engaged in a lively discussion

I’d met him and his live-in girlfriend before, so I didn’t flinch as the others departed. His body and personality reminded me of a Santa-Claus-come-to-the-Southeast type. Harmless.

We wound down our debate and swigged the last of our beers. Then he declared:

“Kim, I’ve really enjoyed our talk and think you’re very attractive.

I’d really like to make love to you.”

I choked down the bile in my mouth.

“Well, I’m flattered and enjoyed our chat, but I’m not interested in you that way.”

I braced for a fight, but he took my comments in stride. We paid our bills and exited the bar.

He followed me to my car, parked just outside the door, chatting amicably along the way. Then he leaned in for a kiss.

It all happened so fast that I can’t remember exactly what Kung-Fu-style moves I used to dodge his jolly advances.

The next thing I knew I sat safely behind the wheel, doors locked; Dirty Santa appeared in my rear-view mirror. Rudolph and his shiny-nosed reindeer be damned, I thought as a drove off!

Case-in-Point #2
A few days later, I sat in my house with a male co-worker. We had hung out many times before as part of a larger job-related friend group. That, plus the fact that he’d recently exited a horrible relationship, fed into my delusion that our friendly gathering would remain so.

When he later embraced and kissed me, it caught me off guard. But truth be told, I responded in kind – I found him hot despite the red flags.

A WTF Debrief
I called Leah that weekend and explained all of the happenings. We’d been friends since kindergarten. I knew she’d put them in perspective.

Her revulsion to dirty-Santa’s behavior matched mine. But she expressed a much-less-shocked attitude about my co-worker encounter.

Ultimately, my childhood friend shared this insight:

“Kim, after years of you wanting to play in the boys’ sandbox, you just need to understand that now men want to play in yours.”

 

 

Leah’s declaration set off a domino effect. The words of my 20-something ex-boyfriend echoed in my mind:

“Kim, men and women can never truly be friends. You might think these guys are friends, but they would have sex with you in a heartbeat, given the chance. Stop deluding yourself.”

Playing in my sandbox? Not truly friends? Say what?!?

My 30-something self made several adjustments in response. Those changes resulted in a small number of f-yous and at least one post-sex high-five with a college buddy. Beyond that, merry asexual sandbox play and real dating exchanges have ensued. But so much for sweet, sweet friends with benefits!

What do you think? Was I delusional – both as a child and as an adult? Do you think boys and girls or men and women can just be friends or friendly? If so, under what circumstances? If not, when does it change?

(This post is one of 30 30-somethings I’m writing for the weekly countdown to my 40th birthday. Celebrate with me as I share other lessons or humbling experiences from the past decade.)