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When Is the Best Time To Make A Move On The Woman I’ve Been Crushing On for Far Too Long?

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Dear KitschMix,

I have a big crush on a co-worker who is also lesbian. But the problem is I can’t tell if she might like me back or not.

I messaged her a few weeks ago and asked her to hang out with me and another co-worker outside of work, so I can get to know her a little.

We’ve been texting back and forth a few times but I’ve initiated every conversation. She doesn’t always reply right away but she also might not be the type to check her phone as often as I do. Mine is practically glued to my hands.

I found out she finds someone at work cute and I am pretty sure I am the only other lesbian (and I’m cute! hahaha). I haven’t really tried flirting because opportunity hasn’t been, but I’m trying to psych myself up to do so.

However, there is a part of me which is starting to think maybe she’s not into me. I’ve been kicking myself for not trying harder to talk to her in person but I get really nervous around her, but I can’t help it because she’s so cute!

Should I see how these upcoming plans go before I start working myself up over nothing. What do you think? Any tips on flirting or advice on my situation in general?

Before I answer your questions, I’d like to start with a little disclaimer. In general, I don’t recommend hooking up with a coworker, as the awkwardness if you break up can potentially be overwhelming. However, I’m going to answer your questions under the assumption that you guys happen to be great for each other. (Just keep in mind, that’s not guaranteed.)

Now, onto your question. I don’t think it necessarily means anything that you’re the one to initiate conversation. Some people are less apt to text, and she might just not be the texting type. (When I’m not working, I’m like you – I generally have my phone somewhere nearby. Although, to be fair, I’m working a lot.)

While it can be hard to tell if there are other lesbians around (no matter how hard we try!), there’s also no guarantee that the woman she finds cute is actually gay. It wouldn’t hurt to try your luck, because there’s a chance it’s you, and you’ll never know until you try. But hopefully you’re able to laugh it off if you read the signs wrong (because there’s a chance of that, too).

I definitely understand being nervous around the woman you like – I still get super nervous in front of my girlfriend, and we’ve been together for over two years. There’s always that slight chance that things are not what they seem, am I right?

I would recommend you see how the upcoming plans go, and maybe make a point to talk to her. You’re going to have to push yourself, for sure – but don’t let your brain talk you out of what your heart wants. Maybe you don’t jump right into flirting. (Besides, you can always do that over text messages – for me, that helps.) But get to know her, face to face, in a friendly situation – and see if it’s worth pursuing.

(Remember how I said coworker relationships can end badly? Yeah… Make sure you really want to be with her before you make a move.)

As far as flirting in general, different women respond to different flirting styles. I’m pretty keen on funny lines, but some women might rather hear about your charity work or your cat. This is another reason it’s so important to get to know her better first. Once you know what she likes, you can “custom design” a flirt plan that actually has a chance.

It still won’t have a 100% success rate, of course – but that’s OK. The way I see it, if it doesn’t work out, was it really meant to be? Try not to take the whole situation so seriously – there’s nothing wrong with being friends first and moving forward from there!

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