Q:
I work a pretty boring city government job that I like fine but usually in the past have just sort of clocked in and out of and left behind when I return home. Lately though, I find myself getting really excited to go to work in a way I never have been, and it’s all because of a newish hire who I’ve been spending a lot of time with. I’m not in a supervisor role over her, and our positions are more or less lateral, though I initially took on a bit of a mentor role for her since I’ve been in the job a while and she’s new to the sector.
I have two problems I’m trying to work out: First of all, I cannot figure out if she’s flirting with me or not. We talk a lot at work and also outside of it. I’ve never texted a coworker this much before. At work, we already have a bunch of inside jokes, and we find excuses to hang out during the day between meetings and spend so much of our time messaging each other even when we’re sitting literally a few seats down from each other. Another coworker even made a joke about us being “work wives,” which I was kind of annoyed about because that coworker is super straight and annoying but whatever. It seems like even other people are picking up on some sort of vibe.
I’m pretty sure *I* am flirting with her…or at least kind of trying to! I’ve never been great at flirting. But even just this chemistry I have with this coworker feels 1,000x easier than when I’m intentionally trying to hit on someone in more of a dating context. But then I start to panic a bit, because that’s my second problem: I don’t know if I’m being messy. And if she’s being messy. I’ve never gotten involved with someone at work, and I know it happens, but it also seems to come with a lot of risk and drama too. I haven’t even looked at any workplace policy yet, but I’m pretty sure we don’t have any rules against involvement so long as no one is a direct supervisor. It’s not that I’m necessarily worried about it being *morally* wrong. More like I just don’t know if I want to get involved in something with someone I work with and am looking for advice on thinking through worst case scenarios here, because right now I’m just sort of consumed with feelings of liking her and wondering if she likes me, too. Help!
A:
It’s hard to know without specifics, but the cadence of your letter and the fact that not only are you sensing vibes but others are too makes me think: Yes, this coworker is flirting with you. Especially if the energy you’re giving is flirtation and she’s matching that or increasing how much she’s talking to you versus pulling back — it sounds like the feelings are very much mutual! So let’s start by operating from that assumption and talk through what it means.
Yes, you’re right, getting involved with a coworker can be messy. I’ve done it in various configurations. I wouldn’t say it ever went great. Even when someone isn’t a supervisor, there are sometimes built-in dynamics that make it complicated. You didn’t go into this too much, but I’m a bit curious about this mentorship role you played — not because I think it’s a dealbreaker for something romantic to develop, but because I wonder if it could impact the potential for a relationship in a way that should be addressed early on. Because also, and I’m sure you could see this coming, a key here is going to be communication. Before you can even get to the point of pursuing a relationship or even casual dating/hookup situation with this coworker, you’re going to first have to talk to her and likely outright ask her if she’s interested in you. Which I know is hard to do! But even though, again, it sounds like there are palpable vibes, you have to get on the same page.
If it turns out she isn’t interested, I don’t think asking her will ruin the workplace dynamic you already have going on. It’ll just clarify some things. If you decide you want to pull back as a result, that’s okay. And ultimately that’ll be better in the long run than living in the weird limbo space you seem to be in right now. So, now, let’s say you broach the topic and it turns out she is interested. There’s still more communication to be had. It’ll be good to set some boundaries up right away, including addressing how you both feel about your workplace dynamics and how you want them to shift or not shift were you to become involved outside of the workplace. You don’t have to do a ton of future planning at the onset, but it’s good to talk out your feelings, expectations, and even hesitations about getting involved with a coworker. Understand that those feelings might shift, too.
Listen, I’d be a hypocrite if I said you should never be involved with someone you work with. It happens. And it isn’t always a disaster either! But I think you’d be setting yourself up for failure if you jump into something without acknowledging there could be some awkwardness and hardships along the way. Chemistry at work doesn’t always translate to chemistry in other contexts. If you’re already texting each other a lot outside of work, then you’ve experimented a bit with other contexts, but it’s unclear to me from your letter if you’ve also spent actual time together outside of work, which would really be stepping outside of the familiarity of your current dynamic. Maybe you could even try hanging out as friends first, see how that goes, and go from there.
There’s so much risk attached to any time we want to shift a relationship dynamic — whether it’s getting involved with a friend, a coworker, an acquaintance, etc. If the workplace chemistry is what matters most with you and you can see yourself being happy with things remaining at that, then sure, keep things the way they are. But the fact that you’re writing this advice letter makes me feel like you’re uncomfortable with the current situation and seeking a shift. And the only way to figure out what that might look like is to talk to her.
Also, check that workplace policy just in case! I doubt you want to risk your actual job for what seems like mostly a casual flirtation at the moment.
You can chime in with your advice in the comments and submit your own questions any time.
Ooh, I just love a good workplace flirt! It makes a dull environment really pop.
It’s good practice for *you*, to be sure. You get to feel more comfortable with yourself flirting, and once you have that base feeling, you can call on it in other situations that are less ambiguous.
For the workplace flirt, I do have some caveats, based on oodles of experience.
Some people (cough cough *straight*) don’t realize they’re actually flirting, and are shocked when you tell them; not much for introspection, they think it’s all you.
Or they’re play-acting, like improv.
Or, in some cases, strangely, it’s actually a power dynamic playing out. I had a mentor-mentee situationship that was really her trying to top me, professionally-speaking. Sour persimmons !
These situations can be awkward if you’ve developed feelings.
Check if you’re feeling vulnerable. Because to me that’s the tipping point, when you have the urge to expose yourself to a potential rejection. Many of us are conditioned to equate having feelings with being rejected, and that’s not a good scene. There’s some very helpful advice on Autostraddle on “Should I tell my crush how I feel”, etc.
You could consider just letting it be fun, in the moment, without worrying about what it means. The Truth will out, as they say.
Flirting is wonderful and powerful ! Revel in your power !