Dear Winnie,

I need advice!

So there’s this guy I work with and he’s nice and cute and I have a HUGE crush on him. We’re not close but we’re not not talking either. My question is how do I drop hints that I like him?

 A lil’ back story, I once confessed to a guy that I liked him and it didn’t turn out so well. We don’t talk anymore and I don’t want that to happen again especially when I work with my crush. I don’t want things to be awkward.

Please advise on what to do.

– Clueless Colleague 


Winnie: First things first: Do you really like him?

“He’s nice and cute and I have a HUGE crush on him.”

Here’s the thing about crushes, and how it’s different from liking someone. Crushing on somebody refers to that specific point in time where you actually only know very little about a person, yet you are infatuated with them. In fact, this phenomenon is enabled precisely because you know the bare minimum – just enough to have positive feelings (see “he’s nice and cute), which allow you to project your desires onto the object of your affection.

“We’re not close but we’re not not talking.”

The reality is, you don’t know him. What are his values? His political leanings? How do they align with yours? He could be nice and cute AND want you to stay at home cooking and cleaning for him, which, if you’re not the domesticated type, could be problematic. The point is, someone can be nice and cute and still be totally wrong for you.

I don’t mean to dampen your spirits or douse the flame you have for this fella. It’s fun to have a crush and it’s exciting to pursue it! However, given that this guy is someone you work with, I’m afraid I have to advise caution and restraint.

“I once confessed to a guy that I liked him, and it didn’t turn out so well. We don’t talk anymore.”

You don’t want to risk this happening with someone you have to see and interact with on a regular basis. Workplace relationships come with a warning for good reason. So, if you want to take this to the next level, you have to be sure that you like him, and that it’s not just a crush.

Let’s start with recognising the crush for what it is: an infatuation based on feeling, not knowledge. Crushes make you giddy. When you have a crush on someone, your mind puts an extra glaze on every little thing that is good about them, making them look like this impossible, magical dream. Crushes are not real. Once you recognise that, it removes the power from your crush so that you can start to see him for who he is.

When I was younger, among the first things that came to mind whenever I had a crush was always, “I wonder if he likes me?” As a grown woman, I learned to take my power back by reframing the question to instead ask, “Do I like him?”

We worry so much about being liked back because we want to feel validation. The problem is, we don’t spend enough time asking if our crush is even worthy of us. Nice and cute is a good place to start but is hardly enough to gauge compatibility. And assessing compatibility is really important in this case because a colleague is not someone you should have a fling with. If you’re going to date, it has to be based on a stronger, deeper connection.

“How do I drop hints that I like him?”

You don’t. Dropping hints pushes for something to develop, and I’m not convinced that’s a good idea yet. I’m an advocate for letting things happen organically, so I think you should just take the time to get to know him more. Toss out the rose-tinted glasses and start seeing him for real. See the good and bad in him. Don’t keep looking for reasons to like him more; instead, look for evidence that the two of you would be well-suited as a couple. Find a way to throw the questions in this article into your day-to-day conversations. Don’t rush anything. Ultimately, trust that what is meant for you will find its way to you and be yours.