Sometimes Ass Backwards Works Better Than Forwards

Timing Is Everything When Dating

His text came out of nowhere last week, though a welcomed surprise.

The last time we’d had a lengthy conversation I’d been somewhat of a bitch to him. It was nearly two months prior, after my ego had been bruised during our short-lived attempt at friends with benefits.

At the time he’d wanted sex and I wanted sex with a side of something he wanted no part of. When I’d found the courage to question him about why being physical with me was okay but actually dating me was not, he was brutally honest about the fact that he simply didn’t feel that way about me.

I wanted to scream at him for using me, but I knew I was ultimately to blame.  I’d willingly made the choice to play friends with benefits, until I realized the game wasn’t for me.

That’s when we ended it.

Afterwards I distanced myself from him. My ego couldn’t take being his friend when I wanted something more.

That nose-dive into friends with benefits wasn’t the first time we’d knocked boots.

About a year before that we’d spent the night together at his place.

At that time in my life my heart belonged to someone I could not have – which meant every man I met while I still spoke to him was a rebound. I’d sleep with most of them once and never speak to them again – but there was something different about him.

He somehow managed to stick around even after our one night stand – often giving me advice and consoling me through some of my shittiest days as a single parent.

He’s a genuinely good guy.

We have some things in common given the fact that he’s a single parent, raising his daughter – who’s the same age as my son –  all alone.

We didn’t continue sleeping together, but we did become friends. We’ve even hung out with our kids.

Since our lives are pretty busy working and raising our children alone, we haven’t been the type of friends that talked every day – but we always reach out to each other every so often with a text or a tweet to say hi.

I can’t explain it, but he always just got me in this weird way few do.

I’m not sure if he was interested in dating me the first time we slept together – but obviously the timing was wrong for me.

And when I found myself interested in dating him this past April, the timing was wrong for him.

I’d pretty much given up on there ever being anything romantic between us until I read his text last week.

“I wanted to know if you would like to go on an actual date with me…”

I didn’t know if it was the best idea to say yes, because in my mind I felt that if a real relationship was going to work between us the sparks would’ve flown for both of us at the same time already – but after a little nudging from him I finally agreed.

I didn’t take the whole thing too seriously – which I guess was a good thing.

This past Tuesday we had one of the best dates I’ve ever been on.

Sure there were moments where it was completely awkward given we were doing things ass backwards. Going from sex to courting isn’t easy – especially when you inadvertently wear day-glo underwear to play blacklight miniature golf and show your date and several strangers a preview of your lady bits – but I think we were both crazy enough to pull it off.

I don’t know where things will go, but we have a second date next week.

It’s been a long time since I’ve had a successful first date that led to a second.

I guess timing really is everything.

And sometimes, ass backwards works better than forwards.

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Related posts:

  1. Lessons In Online Dating: ‘Spin Your Web’ & Don’t Be A Lazy Ass
  2. Just Say No To Casual Sex And Friends With Benefits, If You’re Like Me
  3. Adventures In Friends With Benefits

1 comment

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  1. Amanda Jillian says:

    I’m very glad to see he is the one with the day glo panties mishap. That’s awesome =]

  1. And Then It Was Real - Sex, Lies & Bacon » Sex, Lies & Bacon says:

    [...] Timing is everything. [...]

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