Should You Ask Out a Coworker? 6 Questions to Ask Yourself First

The following is a very thoughtful, thorough response to our post “Should He Hit on a Coworker?” from reader Barbara Arthur, a self-proclaimed “middle-aged female who used to work in career-oriented management positions but now chooses to work ‘just a regular job’ because she thinks management jobs suck (so thinks she can offer various perspectives).” Since the advice is gender neutral, we’ve gone ahead and made the pronouns gender-neutral; our other minor changes for clarity and flow are in brackets:

People warn about workplace romances all the time. Thing is, people meet at work all the time, too — and many a happy relationships spring from that! One of my favorite stories from the place I’ve worked the last couple of decades: people keep gossiping, often not very nicely, about how (names changed) “Sally and Dave sure seem to go out to lunch together a lot.” Sally is my friend; she and Dave met at work years before I started there. They got married. People don’t even seem to notice they have the same last name! [So it can work out. You just need to ask — and answer — the right questions first:]

1. Does the company where you’re employed have any policy prohibiting dating coworkers? If yes, and you want to keep your job, don’t ask them out. You’ll jeopardize your position — and even, possibly, theirs, even though they’re simply an innocent bystander. Management in some companies are real assholes and don’t listen to reason, no matter how clear reason is. If [there’s] no policy prohibiting — well, it depends. Let’s keep going…

2. Are you a job person or a career person? In either case, is it a permanent job you’re attached to or a career-oriented position that you are either attached to or that could lead to even better positions? If so, don’t ask them out. Now, if it’s “just a job,” you’re not that attached to it, well, it depends. Let’s keep going…

3. Just how attracted to/into them are you? There are “other fish in the sea.” Sorta. Frankly, your odds relate to what kind of catch you are, and we don’t know you. Plus, even if you’re the greatest catch, those fish aren’t always so easy to find if you’re working all the time! That’s a big reason why there are so many workplace romances. Thing is, [you run the risk of] making things awkward if they say no — or things being even more awkward if they say yes and things don’t work out. Stuff of workplace legend there. Granted, you’re into them enough to [read this post]. But how seriously have you thought about this yourself? You’d better be interested in them enough to be wanting a pretty serious relationship if you’re considering asking a coworker out — [otherwise] just forget it.

4. Tired of reading yet? Then you’re not serious enough about them. Don’t ask them out. Wanna keep reading? OK: here we go!

5. Now, if you are serious about your intentions, then what about the you-can’t-tell-if-they’re-into-you thing? There’s a couple of ways to find out. Subtly. That’s key. You need to do your groundwork. You can do it yourself, but [it’s] not recommended. If you have to do it yourself, it’s pretty simple. Talk to them. Do they ask you questions about yourself? Your interests, what you’re doing over the weekend, about your family, your dog, anything? Those are all signs of interest and possible attraction. If, after striking up a couple of conversations, do they approach you to talk about anything, ask you for help with anything? That’s a good sign. Do they [fix or] flip their hair when talking with you? Or — a biggie — do they touch you in any way…a tap on the shoulder, slapping your arm when laughing–any kind of touching is a sign of attraction. Nothing’s guaranteed, but positive feedback with those things ups your odds and gives more assurance of a “yes” when being asked out.

But what you really need is a wingman/gal. Have someone else talk to them about you. ***Do NOT have your wingperson ask them if they like you!**** NO!!! Simply have your wingperson talk to them — starting to talk about something completely different, then casually bring you into the conversation — and see what their reaction is. First, simply have your wingperson note their reaction to your name being mentioned. Have your wingperson pay close attention to that. Do they seem to have a positive reaction, neutral, flat, negative? Even no reaction is a reaction (although not a good sign). Then, have the wing person say something positive about you — and have that W.P. pay attention to their reaction about that (same thing: positive, neutral, flat, negative). Then — maybe (and this takes talent…and is only necessary if the wing person hasn’t been able to figure anything out yet) — have said wing person mention something just a tiny bit negative. But do it in a really offhanded, and best of all, humorous way. (For instance: “Did you see when [So-n-so] bumped into the wall and spilled their coffee? Cracked me up!” Do they seem surprised or even possibly defend you? (For instance: surprised: “Gee, anyone could do that” or, even better, defending: “I’ve done that before; it hurt!” or “That’s kinda mean; anyone could do that.”) That’s a really good sign. But if they agree or even share their own negativity, well, that’s a big red flag — but it’s good to know right off the bat than continue to wonder or to pursue something that’s a no-go.

Understand: this all needs to be done subtly, all woven into a very casual conversation, not at all like an interrogation! But a good wing man/gal can be your greatest asset in a situation such as this. And, not to be sexist, but a woman works particularly well. Women dish about guys all the time. So, while a guy can do this for ya, if you can get a gal pal to, she may well be able to get a lot further…she may even get to the like/don’t like territory…but only if the object of your interest goes there first. If they find out that your wing guy/gal has been scoping them out for you, they may be flattered — or they may be creeped out.

6. So, here’s the bottom line: just how important is this person to you, and what’s your priority — your life or your job? You leave your job and go home — and home is where your relationship is. Companies will have policies. Dating within the workplace will have pitfalls — and possibilities. Other employees will have attitudes (and will gossip; it comes with the territory). So — how important is this person to you? Once you know that, you’ll know whether to ask them out.