WARNING: An advice column from someone totally unequipped to give it.

Welcome to ‘Ask Rosie’, the space on Mamamia where you can contact me with your etiquette/relationship/general life problems (including but not limited to eyebrow crabs) and ask me what I would do. Consider it my selfless Oprah-esque gift to all of humanity. Cliche cliche etc etc sassy advice cliche.You’re welcome.

Let’s get into it:

Dear Rosie,

There is this guy at work that I’m kind of interested in and I’m fairly certain he likes me too. We flirt a lot and even had a sneaky drunken pash once. I know that if I made a move we would probably start seeing each other, but I just have so many doubts, especially since we work together. What happens if it doesn’t work out? I want to take a leap here, but I just don’t know…

What would you do?

– Jess

Okay Jess, I’m going to tell you a little story. It takes place in 1998. It was a simpler time; Chumbawamba was awesome and everybody was doing that sex-hand thing on car windows after seeing Titanic.

I was a fresh-faced 7th grader, covered in freckles and many, many years away from understanding out how tampons work. You know those cool girls you remember from high school? The ones who were pretty and had boyfriends and knew all the words to the talking part at the beginning of ‘Never Ever’ by All Saints? I was not one of those girls. I was awkward and shy and partook in super cool activities like studying and watching television.

It was under that backdrop of 90’s awesomeness that I developed a major crush on a boy. His name was Stephen and he was smart like me and kind of lanky and I loved him. I may or may not have practised kissing him on my sister’s Baby Born (a disturbing image, I know, but it just had a more realistic mouth situation going on than my teddy did).

Now, given my aforementioned awkward demeanour, naturally I assumed that me imagining his face while I made out with toys was as far as this thing was going to go.

But then he gave me a note. (Technically his friend passed my friend Melissa a note on his behalf and she then passed it to me but that was just the way things worked in Year 7.)

It said:

“Dear Roseanna,

I like you. Will you go out with me?

Stephen”

First of all, my name doesn’t have an ‘e’ in it, but I considered it a glorious poem on par with Shakespeare nonetheless.

Now, Jess, this is where my life hit a similar crossroads to the one you are facing with drunken pash work dude right now. I had the chance to begin an epic romance with Stephen that would no doubt involve lots of hand-holding and lips-only kissing.

But I chose the other road, Jess. I chose the other road.

I freaked the fuck out about the note. I was too embarrassed to admit that I liked him, so when Stephen’s friend asked me if I got the note (while he stood hopefully to the side), I said that I had but that I had thrown it away. Then I swished around on my Colorado school shoes and went to class.

I still can’t explain why I did that, but I always regretted it. I mean, I don’t want to paint with a broad brush here, but I’m sure if I had just gone for it, Stephen and I would have had one of the great romances of our time. Like Britney and Justin. Or Oprah and Gale. A couple of years later I went away to boarding school and never saw him again. If that’s not a heartbreaking tale of star-crossed lovers, I just don’t know what is.

So, Jess, my advice to you is this: If you like the guy, don’t over-think it. Just go for it. You don’t want to spend years regretting all the hand-holding and matching double-denim ensembles that could have been.

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Have you ever dated a colleague? Any advice to share? 

If you want Rosie’s advice on something, email her at rosie@mamamia.com.au and put ‘Ask Rosie’ in the subject line. Of course it will all be completely anonymous. And she’ll only judge you behind your back.