#1034: “My coworker messaged me on a dating site.”

Hi Captain,

My question is not exactly high-stakes, but I’m having some anxiety about this situation all the same, and not sure what to do.

I (she/her) started using OkCupid recently, and a couple days ago, my coworker (he/him) who I don’t know well but see around often (we work at a very small company) sent me a message. I know it can be fun to send a couple silly messages back and forth when you see your friends on these sites without making it weird, but I don’t think this is that.

Anyway, if I see coworkers on dating sites, I think the polite thing to do is just ignore it and move along, so I was not super into the fact that this guy messaged me but I figured he was just being kind of socially obtuse. His message implied that he was going to ask me out “until he realized who I was,” which made me immediately uncomfortable. Dude, if you realized that, why did you message me anyway and tell me that?

I felt like ignoring him might make things weird at work, so I just messaged back noncommittally (like, “Ha, look who it is”), hoping I could move the conversation to peter out without making it awkward. However, things got awkward anyway, because coworker continued sending messages despite my polite attempts to disengage (“[Cool, unsolicited weekend plan you shared] sounds fun. Anyway, see you Monday!” …and then he’d send another message trying to continue the conversation.) I read and did not respond to the last message.

I’m sure I should communicate that I feel uncomfortable chatting with a coworker on a dating site, so do you have any scripts for that? Or would it be better to just block him and pretend it never happened? In hindsight, I feel like there are other things I could have said or done to end the conversation sooner, but that’s only now that I know I wasn’t able to end it without confrontation. It might be useful in general to know how to stop an inappropriate interaction like this in the future, so what would you have done?



Hello OkAwkward!

It’s not inherently weird to be on the same dating site as other people you know in other contexts. It feels weird because the illusion of privacy has been punctured for a moment, but it’s not actually that strange. The awkwardness is in what people do about it.

I believe I have shared the story of the Shadowy Dating Juggernaut where Commander Logic and I and both of her roommates and a few other friends in the Bespectacled Bookish Brunettes of Chicago Knitting Circle And Culinary Society were on OkCupid at the same time, right? It was inevitable that streams would cross and one of us would bring a dude we were dating to a party and watch him slowly figure out where he knew the rest of us from…because if you liked one of us enough to write to you probably liked all of us…and that we all knew each other….and that we had definitely had been trading notes about him behind the scenes in the name of safety, solidarity, and hilarity.

When seeking romance (etc.) on the great wide Internet it is inevitable that we will run across people we know in other contexts. Like you, my strategy has been either to totally ignore it or to be like “Oh, ha, look who it is. See you at work, Work Person!” and then drop the conversation completely. Whether I ignored or said something depended a lot on context and the vulnerability of what was on display in their ad. “My mom and my friends say I’m funny and I like long walks on the beach and living life to the fullest” guy got a “hey, hilarious that we’re both here, good luck bro!” Someone revealing kinks or more explicit sexual content or desires just got ignored and in some cases insta-blocked more so that I wouldn’t make THEM uncomfortable or feel like they were being monitored. Mostly my attitude was “No shame, no foul, and no gossip unless you do something actually creepy.” And if it ever came up at work, I’d be like “Whoa, awkward, right? I won’t talk about it if you won’t, and heyyyyyyy good luck out there buddy!” #don’tcrossthestreams

Another true story: Years ago colleague who was new in town messaged me once on OK Cupid and we went for a friendly coffee before we knew we’d be working together. Then we got assigned to co-teach a class. Upon being “introduced” at work, we never mentioned or even hinted that we had met each other before in any other context. Yay professionalism!

If your coworker has got overall good intentions and is also feeling awkward about what to do next like, “aaaaahhhhh, I started this, do I have to keep emailing her now back and forth forever, ugh, so awkward?” he will gratefully take your lead. And if he’s not taking your lead, like now? Then don’t reply to anything else via the dating site, or, reply once to say “Hey, let’s wind this conversation down, I’m not interested in connecting here, see you at work” or “Hey, let’s block each other here so it’s not super-weird to have a coworker hanging out whenever we log in, ok? Good luck out there!” and then block him. Blocks are not mean. Blocks are often necessary to make a social site usable.

Then, keep work conversations only about work and wait for the awkward levels to normalize.

And, if your colleague won’t drop the subject and starts bringing it up at work, making you feel like he’s monitoring your dating and sex life, and making your life weird at work? DOCUMENT THE EVERLOVING SHIT OUT OF IT. America needs about 100,000,000 uncomfortable training sessions led by HR right now.









76 thoughts on “#1034: “My coworker messaged me on a dating site.”

  1. Aside from the stuff the Cap mentions, people have pretty different ideas of how to use dating sites (and even just how to date) and that can make for a lot of weirdness if people with different outlooks encounter each other. Before I was an old married and in the early 2000s wild and wooly online dating world, I viewed online meets as a more elegant equivalent of an initial meet in a bar or park. I’m there to have an initial meet with someone and decide if there is enough reason to have an actual first date. I didn’t waste time with folks I had major deal breakers with or negative compatibility, but I didn’t see myself as able to learn much more than that up front. Sometimes I’d connect with someone who wanted to have a deep interpersonal understanding of each other before ever seeing each other face to face, and there’s be some challenge there since I was of the “let’s suss out our chemistry sooner than later” person. Sometimes you meet people who are only looking for casual encounters, ones who are or are not open to meeting new friends, ones only on the marriage track, etc and so on.

    Which is a long winded way of saying maybe this work person thinks absolutely nothing about using this as yet another twitter for casual chit-chat. I’m about done in this world with giving my fellow men a presumption of good faith when it comes to their interactions with women. But this seems like a situation where there’s not an equally bad faith interpretation to his actions. He’s confined himself to stuff that would be benign hallway chit-chat and he’s done it in a place where you can just ignore it or even (presumably) block him. Even just calling it socially awkward is predicated on identical views about encountering people you already know in real life and workplace dating.

    I can’t speak for any other man in the world, but back in the day if someone had said to me “peace out, it makes me feel weird to have causal coworker chitchat in a venue I view as for dating so let’s not engage here anymore” I would have just chalked it up to a difference in dating attitudes. Assuming I didn’t agree, that is.

    1. I don’t know…he did imply he would have asked her out before he realized who she was. Sounds like testing the waters to me.

    2. Hopefully co-worker is not messaging LW on the company dime! He may need some education in the lack of online privacy and the employer’s right to monitor all communication (if they’re in the US).

  2. Captain gives great advice, as always. Let me chime in with the blocking-is-you-friend choir that I’m sure is forming around this post as I type. The amount of friend-friends I’ve block on OKC at first glance of their profiles, that I was too embarrassed to read, is surely in the double digits. It was never even mentioned between us afterwards. Go forth an block fearlessly and without guilt.

  3. I was on dating sites. I would think nothing of blocking a coworker if one came my way. My private life and my work life are two very different arenas and the two shall hopefully never meet.

    That said, if a coworker got to me first, I would keep it polite and professional with a “Oh hi! Funny meeting you here! See you at work!” That’s the shutdown to further conversation online. If anything is said in person, I told the truth, “Well, I’m on there, but I hafta say, I don’t date coworkers. I like to keep the worklife and the private life separate, you know? (with a knowing wink like I”m positive he feels the same). (And that was the truth – my personal rule not to date coworkers). Tone of voice is no different than, “Should we use the Helvetica font or the Times New Roman?”

    If you don’t make it weird, it shouldn’t be weird. But if they insist on making it weird -especially at your actual workplace – that’s what HR is for.

          1. @whingedrinking out of nesting.

            I had a prof who dinged for font choices, but that was because he spent like 20 minutes explaining serifed fonts with examples, and the told us we had to use a serifed font. He made the rules very very very clear.

          2. Angel, I get it if he made the rules and expectations extremely clear. I once had a teacher who refused to let us use the word “very” under any circumstances, except quoting other people who were “stupid” enough to use it. Grrr.

            However, I’ve also had teachers who played a game of “guess what I’m thinking,” and would ding you for the most ridiculous things, including getting the answer right (with PROOF!), while the textbook had a verifiable typo (He wanted us to ignore the known truth, and parrot back the typo, even though he, himself, admitted it was wrong).

            IME, grades do not indicate true intelligence, or even true expertise in the subject matter for that class. Grades indicate how good you are at pleasing that teacher.

      1. My handwriting was (and is) a teacher’s nightmare. I’m sure they were just grateful when I did not have to handwrite. I feel bad for the poor profs who had to grade my exam blue books. In other words…they would not have card about the font!

  4. My ideal coworkers-on-dating-sites is: We recognize each other from the pictures, and we all instinctively recognize that crossing the streams is awkward, so we don’t like or message one another on the site, never mention it in person, and basically pretend it never happened.

    But expecting everyone to be instinctively on the same page as me doesn’t tend to work well in the real world. So, my realistic coworkers-on-dating-sites expectation is: If the other person likes or messages me, or mentions it in person, or otherwise acknowledges it happened, I get to tell them, “Wow, what a coincidence! I’m not comfortable with dating a coworker, though. Good luck, see you at work!” As long as they cut it out at that point, we’re all good.

    If they continue to message, I get to block them without feeling bad about it. (I could do this at any time, of course, but I personally need some kind of guideline for when to not feel bad about it, or I would always feel bad about it; this is one of my guidelines.) If they continue to mention it in real life, or if they bring it up at work ever in any context: “I don’t like to mix dating and work. Please stop talking about my dating life.” At this point, I’d document any further mentions, and ask for support from manager and/or HR if they don’t cut it out after that very clear boundary was set. (It’s never gotten that far, but I like having a plan for just in case it does.)

    1. When you block someone on most of these sites do the messages all disappear from your view? Could be worth screencapping stuff as a just-in-case someone doesn’t take the polite brush-off and you need to show evidence to HR.

      1. I have no idea, honestly, but if you needed to I’m betting you could unblock and get access to old messages again, screenshot them, and reblock. Blocking generally doesn’t mean the old stuff gets deleted–just hidden.

  5. I don’t think LW has spelled out clearly that she does not want to date Co-worker.

    “Funny meeting you here, but we work together. For that reason alone, I’m not interested in dating you” ought to do it.

    The rest of her statements sound like hinting or teasing or flirting around the work situation. This situation calls for bluntness. THEN stop responding to anything he says on the dating site unless it’s to go broken record mode on the same sentence given above.

    Continue being absolutely normally professional when at work.

    1. I agree – I think this needs a simple but very direct boundary that I don’t see has been set yet. Tell them you’re done chatting on OK Cupid (or wherever – not being on dating sites my coworker line is Facebook) and then block them.

      1. My go-to line with Facebook is just, “I never add coworkers on Facebook,” which has always worked well for me. I think because I state it as a blanket rule (which it is for me), so people are less inclined to take it personally.

        I’m not on dating sites, but wouldn’t something similar work here? Just a quick, “Hey, I don’t chat with coworkers (or people I know from other things) on OKCupid. See you at work, though!” Or if you want to block them, just explain that you auto-block coworkers on dating sites so things don’t get weird.

    2. I definitely get the vibe that the coworker is trying to date her, too. The coy little “I would ask you out if we didn’t work together, but we do, so I won’t, which is totally why I’m messaging you on this dating site, tee hee!”

      1. That struck me as a possibility too; maybe the continued chit-chat is purely being sociable or maybe it’s a keeping the communication open in case LW might actually be interested. In a fair and just world men would take the hint from a lack of enthusiasm in short order and piss off, but for everyone else there’s block.

        An explicit “I don’t feel comfortable communicating with a coworker via this” and/or a “I don’t date coworkers” is something that would be a nice above and beyond, but certainly nobody is owed that.

        1. Yes. I think OKCupid is a bit different from Tindr and other dating sites (although I haven’t actually used match-dot or plenty-of-fish so I dunno for sure about them) in that it was set up to also allow or encourage meeting new friends, participating in forums, and general chat with a plausible-deniability of whether or not the chatting was with intent to find people to date. So I think the LW should say “I don’t talk to co-workers on OKCupid” rather than just “I don’t date co-workers” – otherwise the clueless-colleague might think/rationalize it was fine to keep chatting on OKC just like they’d chat if they frequented the same coffee shop or commuter-rail station.

    3. I don’t know. To me that sounds *very* blunt and could be misconstrued (deliberately or otherwise) as rudeness, leaving the LW to have to do a whole lot of work and ego massaging if they need to preserve a good work relationship with this person. It also leaves the LW open to the classic rejected-bloke-on-a-dating-website move of ‘Urgh, well of course I didn’t want to date you, I was just being friendly, jeez, up yourself much?’, which again, awkward for ongoing working relationship.

      I thought the Captain’s soft nos were a perfect balance between subtly but clearly deflecting dating-type interest, and letting everyone save face enough to minimize awkwardness at work.

      1. LW here. Thank you everyone for your thoughts! I’m replying specifically to this comment because this is exactly what I had in mind when I shied away from the very direct “I won’t date you” route. This sort of plausible-deniability scenario can be pretty difficult to navigate when you want to directly communicate a lack of interest just in case, but the other party hasn’t directly communicated any interest in you. His message did appear to be trying to gauge my reaction (as some others here have pointed out), but I would still feel awfully presumptuous to just assume that he wants to date me. For this reason I much prefer the “Hey, I actually don’t want to chat with coworkers on here; nothing personal!” route that the Captain suggested.

        If anyone wants an update: I sent back something along those lines and I am pretty sure he saw it but didn’t respond (the site indicates he’s been online since then), and I don’t want to keep feeling anxious about this or feel like I need to check his login times to make sure he saw it (that feels creepy?), so I ended up just blocking him. I’m hoping he won’t bring it up at work and it will all just blow over. Luckily we don’t interact a lot on the job.

        Finally, I really need to repeat this mantra: Blocking is not mean! Thank you, Captain!

        1. Yay, you! Hopefully his silence was just him respecting the “let’s not talk on here any more” boundary.

  6. I keep getting suggested as a match on dating sites to a good friend of mine and they get suggested to me. It makes sense! We’d be a good match if we hadn’t both already decided that we’d kill each other in anything long-term or in depth. We’ve even had sex a couple of times!

    With them, what I did when they showed up for me on OKCupid AND Tinder is I sent a brief jokey message that was mocking bad dating site messages, they sent me one back, and we left it at that and kept up normal communication elsewhere.

    This is a bit different because we’re already very close and intimate and nothing revealed on their profile was a surprise to me and I doubt mine was a surprise to them. Workmates are trickier, but I think a ‘hey, I’d rather not talk on a dating site with someone I work with’ or similar would be fine with a reasonable human. Both of you go around with the slightly awkward knowledge that they are in fact a squishy human with squishy human wants and desires and needs, and hopefully you both put that knowledge in the little ‘not my business’ box where it belongs in a work environment.

  7. “His message implied that he was going to ask me out ‘until he realized who I was,’ which made me immediately uncomfortable. Dude, if you realized that, why did you message me anyway and tell me that?”

    It’s a neg. He sent it to you hoping that you would reply and either let him know you’d be also be into it except Work or you actually are into it, even though you work together. If you are not into it, he’s counting on your professional courtesy or supposed fear/shame of being outed to coworkers for being on a dating site to continue the dialog with him even if you might not want to.

    1. Does it have to be a neg? Or trying to pressure/shame her?

      I think it was definitely a message that, if she didn’t find the work thing a problem, he’d like to know. Because hey, maybe they’ll not be working together, and then he might really ask her out.

      And it might be a way for him to say, “hey, i saw you were on the dating site, and so am I, so now we both know.”

      Oh sure, it might be–so of course, be alert. But see what other info comes your way.

    2. How is that a neg? I’d read it as the opposite (a pos?): you’re a woman I find attractive and would like to date, and the most important reason I won’t attempt to do so is that we’re coworkers, not because there is anything wrong with you.

      It could indeed also be an attempt to date her anyway. But it could equally be a slightly awkward ‘fancy seeing you here’. I think I would just stop replying and see if that helped.

      1. That’s how I interpreted it too. On the surface as a “oh hey, your profile was neat enough that I thought you were dateable! Whoops, we’re coworkers though!” and perhaps a low key “…unless you want to?” implied

        1. Yeah, I read it like that too, as a question rather than pressure. From the letter it sounds like she isn’t interested and just wants to stop the conversation, so I think something like ‘I don’t really like chatting to coworkers on dating sites but see you at work :)’ would probably be how I’d go. Probably with a block shortly afterwards to reduce embarrassment. I might even tell them I was blocking them to avoid both of us being embarrassed, or I might just go ahead and do it.

  8. I’d try to close the door firmly on any kind of romantic context *and* anything he could negotiate about, like whether he does or doesn’t find it awkward to chat with you there or see each other in the pool. Maybe “Okay, well, I have a strict ban/block policy on coworkers here to keep those two aspects of my life separate, so while this was a fun coincidence, let us never speak of this again. 🙂 See you at the office!” If you think it’s useful, you could wait to see if he’s got a response before you block–doing it right away has the advantage of sending a clear message, but there’s information if he responds with “Okay, cool” versus negotiation or “But whyyyyy” nonsense. But definitely blocked before you see each other next.

    He gets no more than one pass on bringing it up at work, which should get a firm “I thought I was clear, we’re not going to talk about that” before it goes to HR or the boss or whoever you’ve got at a small company to deal with personnel issues.

    1. I think this is pretty dramatic. One pass and you run to the HR? If the person doesn’t get it, how about telling them that you will go to the HR if it happens again instead of running to the boss over it? If I was in management, I’d rather not have to know about or deal with this kind of personal business unless really necessary. I wouldn’t be surprised if it was “held against” the complainer even if not overtly.

      1. I have been management. There were plenty of things I’d have rather not have dealt with, but that was my job so I did it.

        How many times should someone have to be told no before they should be expected to listen? Two? Ten? Once online and again in person seems like one more than is absolutely necessary; this isn’t a baseball game where there’s a promise of three strikes before you’re out.

        As far as the possibility that involving HR might result in inappropriate retribution against the reporter I would be shocked if there’s a single woman in the workplace who needs to be reminded of that.

        1. How many times should someone have to be told no before they should be expected to listen? Two? Ten?

          Exactly! The idea that a grown man capable of holding down a job can’t understand a No is not just ridiculous but profoundly insulting to men. Small children get told no repeatedly until they get it, adults should only need to hear it once. I just don’t understand why people think grown men need to be protected from the obvious and predictable consequences of their freely chosen actions as if they’re small children who don’t know what they’re doing.

          With the caveat that I’m not a manager, if I were I’d want to know if one of my employees was incapable of respecting a no like a grownup. If a grown man has to be smacked down repeatedly like a badly trained dog, I don’t want him on my team. When else will he refuse to respect a no? When I tell him he can’t leave early? When I tell him he can’t have the assignment he wants? When I tell him that the work he turned in needs changes? Even if he never escalates to open sexual harassment, I’d still rather hear about it and know to keep an eye on him than be surprised by a serious team issue that I should have known about.

        2. You must have far more knowledge than me about the readership of this column and the bent of all HR departments.
          Personally I’d prefer to keep my job, stay low profile and not complain about something so inconsequential as e-mails I can ignore or block.
          I only speak for myself in my profession, of course.

          1. So now you’re gonna add “women should just ignore it” to the suggestion that women are unaware that retribution against reporting sexual harassment is a thing? I cannot wait to see what you’ll toss on here to make the trifecta.

          2. Can we end this subthread? @Bydabayou literally no one is suggesting going to HR as a first stop or before attempting to block or otherwise handle the situation oneself. It is only coming up as an option if the perfectly reasonable step of blocking/ignoring a coworker on a dating site or saying “I’m not interested in dating you” has unreasonable work repercussions.

          3. Pleases don’t put words in my mouth Don Whiteside. Learn to speak for yourself, not me, not every single woman in the workplace. Thank you.

          4. And please stop posting in a discussion when I ask you to, @bydabayou. How many times has some condescending generalization you’ve made been called out here and turned into an argument? Is it every time or only every other time? (Don’t answer that. It happens a lot.)

            Nobody loves running to HR about stuff like this. Nobody suggested it as a starting point or instead of dealing directly with the dude. All Don did was say that you can go to HR if your own attempts to shut it down don’t work. That doesn’t make you weak or a time-waster or a bad team player. Also, people who hit on their coworkers take a risk when they cross those streams. There’s a reason workplaces discourage it and/or have rules about it. Can the risks accrue to men who won’t take no for an answer for fucking once instead of to the women who are the object of these advances? I think it would be cool if “Shit I should probably leave her alone, it might become a work issue if I make her uncomfortable” became the default setting.

      2. Uh, not dramatic. If LW follows the script, the guy has been told nicely online that they want this to be the end. If the niceness is somehow misinterpreted as encouragement (because society) and then brings it up at work, he will then be told a second time not to discuss dating stuff with her. At that point, he does not need or deserve a warning that she actually really really means it and will involve someone to whom he will actually listen.

        I wouldn’t want to have to deal with this as a manager either, which is why I would be pissed at this guy for bringing this into the office. It is 100% his fault, and that is how I have dealt with it in the past. (My situation was my direct report making dirty jokes to a lower level guy–both presenting as cis-het, if it matters. Yes, the lower level guy could have told him no a bunch of times with increasing insistence, but that was not his responsibility. Mine was to shut down my direct report, keep an eye out for continued problems or retaliation, and be prepared to terminate if there were.)

    2. Yup. One “ok, so I’ma block you on this b/c it’s weird to have coworkers on my dating profile, peace,” and then a block.

  9. I work in a really small department. A co-worker and I both got divorced (from different spouses) at the same time and we began using dating sites around the same time as well. We had one awkward “soooo I see we just got matched on this site!” conversation in person and we both agreed “nope, it would be a bad idea for us to try dating for a lot of reasons, so let’s mutually unmatch each other and just pretend that we don’t exist in those shared spaces.” Many years later, we are still co-workers and friends and he’s married to someone he met through online dating.

  10. There’s a joke this reminds me of:

    Jews do not recognize Jesus as the Messiah.
    Protestants do not recognize the Pope as the leader of the Christian
    Baptists do not recognize each other at the liquor store.

    There are precedents for this. Your co-worker isn’t following them. If you’re not comfortable telling them to knock it off, (or you do and they don’t, ) block them. It’s not like they can complain to HR that you’re not replying to their OKCupid messages. (Well, they CAN, and wouldn’t that be a great bar story for the HR employee!?)

    1. To be fair, the precedents for coworkers and dating apps aren’t universal. Some people are fine with dating coworkers, and therefore see no problem with chatting with them on dating sites. I saw this a lot in my last workplace, where the company was big enough and employed a big enough chunk of the local population that plenty of people ended up dating other people within the company. In a scenario like that, most people don’t want to work with the person in the next desk over, but many are fine with dating someone who works in a different area of the company…and how close is too close varies a lot from person to person, as it turns out.

      1. Yes, I think that’s actually a reason meeting a coworker on a dating site is awkward – because there may be no cultural concensus on whether or not dating coworkers is a problem or not.

        Some situations are a clear no, like dating up and down the management structure but for more horizontal situations where there isn’t an actual ethical problem, everyone seems to have different preferences. Some people date and even marry coworkers, others see it as almost incestuous and would never consider it

    2. Hah! Such a true-ism! (I grew up Catholic with parents who worked at a Baptist university in Texas –I heard that joke AND witnessed it playing out in the liquor store a lot).

  11. Is it inherently wrong to ask a co-worker out either on a dating site or by some other means? I’m currently happily dating a co-worker after meeting at a non-work social function, having fun being social with them, and then asking them out. It didn’t occur to me that it was not an OK thing to do.

    As far as I can tell where the writer’s co-worker went wrong was messaging her in a way that was unclear and likely to result in confusion and awkwardness. Seems that he should have either:
    1) Clearly asked her out in a way that gave her the opportunity to say “yes” or “no”. Obviously if the answer was “no” he should drop it and move on.
    2) Don’t message her at all and never even mention that you saw her profile.

    Is this about right or am I missing something fundamental that would make it inappropriate to ask a colleague out in the absence of a supervisor relationship or a specific work policy against it?

    1. I don’t think it’s inherently wrong but I also think that people should do what you outlined – make a clear ask – and also be prepared for an “ugh no we’re at work” reaction. Like, recognize that’s a risk and be able to take no for an answer. If rejection is going to make it hard for you to be around the person, leave them alone? If you supervise them or are senior to them, leave them alone? And, If you are a relatively privileged person (I.e. A man asking out a woman) think hard about the gender dynamics in your industry and whether you want to contribute to women feeling objectified and pressured at work. Think of yourself in terms of a gauntlet the object of your affection is running vs. a singular well-intentioned person.

      1. Think of yourself in terms of a gauntlet the object of your affection is running vs. a singular well-intentioned person.

        Thiiiis! Guys, you are not the only man to think it’s amazing and sexy that a woman programmer can program and be a woman at the same time. Leave the one woman on the team alone. Don’t hit on the receptionist or admin assistant either – she’s not flirting, it’s literally her job to be pleasant and helpful.

      2. This.

        Also, if you’re a heterosexual guy, and you look around and your workplace is 75-80% male, then you’re probably not the only one hitting on your female coworkers.

        One person doing it is annoying, and not to be minimized, but when a woman ends up dealing with 10-20 “joking” conversations about their looks, their femaleness, their dating life, the “if I were 20 years younger” jokes, the flirting banter, every single month? It gets oppressive, fast.

        And if you’re one of the women, you run out of funny, cute, light-hearted soft no’s reeeeeally fast.

        And honestly, it’s not the woman’s job to keep men’s attempts to hit on a work colleague from being awkward. It’s work, not a singles bar. That crap should be awkward.

        1. I think it’s also important to note that random_username started asked this person out after hanging out in a non-work social situation. That’s a pretty big difference than asking someone out while you’re both at work (which I’d find inappropriate in pretty much every case).

          1. And I met my current husband at work. And we now still work together, fairly often, in a different industry. But we stay away from PDAs at work, enough so that someone who worked with us both on one 8 year long project didn’t even know we’d gotten married in the middle of it.

            Work’s not the place for private stuff, and DH never made our private relationship a workplace issue. And neither of us asked the other out at work.

            I was replying to Captain Awkward’s response about the awkwardness of getting hit on by a work colleague, not random_username’s post about hooking up after hanging out in a bar. I agree there’s definitely a difference between the two.

            But I still felt it was important for someone getting ready to ask a colleague out, to realize that even if you only approach someone you work with in a social situation, they may still have a knee jerk reaction to being approached. Because whoever is lower down the chain of command, even if they work in different departments, can find their commitment to their jobs and work ethics being questioned, even if they keep it professional. Especially if they’re female.

      3. I’m okay with the baby-step-plausible-deniability option at work–I got kind of asked out that way at work, and once I realized what happened, I was glad that we both had the fig leaf that he was asking a new buddy out for a group bike ride and I just wasn’t interested in cycling. But the pseudo-asker has to take any negative response as a rejection of the hidden romantic intent, even if it’s still possible that I would have loved to bang the guy but was just not into bikes. No “Well, if you don’t like bikes, how about coffee instead?” No “What I actually meant was….”

        Just like an overt inquiry, a covert inquiry needs to stop dead if not given enthusiastic agreement. It’s up to the receiver to volley back if they change their mind or realize “Whoops, he might have been interested, maybe I should invite him out for paintball.”

        1. I’m still not a fan of this at work, even with your caveat. It seems too risky that the askee doesn’t realize it’s a fig leaf and really does just want to make some friends and ride bikes. When that gets cleared up down the road, it’s going to be way more awkward than a direct “would you like to go on a date sometime?” “No, thanks.” conversation would be.

          And on the other side, as a woman-type person I would love a universally understood “all workplace romantic overtures will be exceedingly direct” because I would love the freedom to accept social invitations from cishet dudes knowing that they are 100% platonic. And if I was a cishet dude, I would like to be able to connect with colleagues on that same assuredly platonic level.

          1. Yeah, when I was a girl studying in a majority male STEM degree program, this really messed with my ability to make friends. I would have class-friends, and we would chat or joke around in labs and seem to get on well, but every single time I suggested anything outside of class to a male acquaintance, walls would slam up.

            It was lonely.

            I wish I had known better how to clarify I was just trying to make friends. My experience was far from the stereotype of the nerdy girl always being hit on. Much the opposite.

    2. You’re missing a few fundamental things that don’t add up to “never ask out a coworker” but do add up to “think really hard about whether you should do this, and err on the side of ‘no.'”

      1. You have to keep seeing each other.
      – If s/he says no, you now have to see someone who rejected you every day. You get the daily reminder of someone who didn’t want you, and they get the daily reminder of the fact that you might resent them for the rejection, or might not be able to work professionally with them because of your romantic/sexual interest.

      – If s/he says yes, it can go worse. Whether the date goes bad, whether the relationship goes bad, whether you had an argument the night before about the dishes, you still have to work with each other.

      2. You’re probably not the only one to ask, and at least a few of the other ones were creeps.

      – The person has probably been asked out repeatedly at work: by the person who didn’t let it go and kept pestering them, by the person who implied that saying no would be bad for a career, by the person who pretended to be just a work friend and then grabbed his/her ass, etc. Most people who try to dip in the company ink are sexual harassers and creeps. You’re now in a category that generally adds up to “people that have made his/her life at work more difficult,” so your advances are probably not going to be appreciated.

      1. ” If s/he says no, you now have to see someone who rejected you every day.”

        Good point, I hadn’t considered this because it wouldn’t be an issue for me.

        In fact, I think it would be more difficult for me and more weird* for them if I was [attracted to a person but not pursuing it] rather than [asked for a date and got a “no”] because in the second case I would (and have) just shrug and move on.

        I realize that this will vary from person to person based on how somebody deals with a rejection. I’m solidly in the camp of “no big deal, glad I tried, back to normal”. There are 6+ billion people on Earth. I assume the vast majority of them would not want to date me, so when there are literally billions of people in the “no thanks” camp what difference does one more or less make?

        *Not saying I’d deliberately make things weird, but there’s likely to be some emotional/behavioral leakage anytime somebody is interacting with a person they see as a potential romantic prospect, even if they’re trying to be 100% professional. When somebody at work is crushing on me I much prefer they just say something about it and clear the air rather than leave me to pick up on flashes and hints of interest that sneak past their professionalism filter.

      2. And your #1 – if she says yes, it can go worse can affect your #2 – You’re probably not the only one to ask. Because those creeps often assume that if you’ll go out with one person at work, you’ll go out with ANYONE at work.

        The creeps often seem to assume they’re not creeps, and the 45 year old guy from accounting you barely know but always seems to drop by making off color jokes = the hot guy your own age who you have a secret crush on. In their mind, if you agreed to go out with the hot guy you like, then you have no good reason to turn down the creepy guy you don’t.

  12. Oh, hey, I recognise this game he wants to play; it’s called Just Good Friends.

    “I know we’ve ruled out dating up-front, so let’s just be friends. And because we’re just good friends, completely platonic friends, I can jokingly flirt with you. Isn’t that funny? It means nothing, of course. It’s what friends do!”

    It’s avoidant as hell, and for the same reason it’s hard to argue against. You wouldn’t tell him he can’t be your friend, would you? After all he’s such a nice guy…

    Which is not to say he’s *intentionally* being manipulative. Odds are that the main person he’s trying to fool is himself. But still, don’t feel guilty about cutting that shit off as abruptly as you want.

    1. Oh, I know that game too.

      I didn’t get the sense that you meant “avoidant” as in “avoidant attachment”, Tattie, but that wording made a lightbulb go off for me. It’s absolutely avoidant as hell that way too. The Ruled-Out Flirt Buddy is total catnip for avoidants. For a really devoted avoidant, it’s even better than a romantic relationship. (Besides, stereotypically a strong avoidant on a dating site would be nursing a bruised heart over their Perfect Ex, the same one they drove away with criticism and withholding.) How lovely for an avoidant, to get that flattering attention at their convenience without ever having to worry about being called on for any kind of meaningful connection. How safe, to know that if it ever looks alarmingly like it means something, they can back out in a hurry and leave you holding the bag like a chump.

      There are reasons why avoidants wind up overrepresented in the dating pool.

      Nothing good comes from playing that game.

      1. I did mean avoidant attachment, McStabbity, but reading up on it, I was more thinking of the “fearful avoidant” style whilst you seem to be referring to the “dismissive avoidant” style. I could see both types of person making use of very similar tactics though.

        Folks, it’s OK to be avoidant– that doesn’t make you a bad person or unworthy of love. But these games need to be consigned to the bin. They only end up hurting you and the person you want to get close to. (Ask me how I know…)

  13. I am the complete opposite in the sense that I can’t imagine ever dating someone who is NOT from work. I’d give anything to find my Ms. Right in my workplace (preferably someone with the same degree as I have — I’m in academia).

    That said I fell in love with someone from work who is the complete opposite — will never mix work and personal life. I didn’t know that until I asked her out and she literally freaked out (and months later I had to hear the whole “we are coworkers” crap).

    Maybe this guy doesn’t have the same values as LW and he just can’t figure that out if she doesn’t tell him that. LW, just set your boundaries, this guy clearly was testing the waters but he isn’t a mind reader.

    1. I’m always so amused by the very dramatic split I’ve observed in people with advanced degrees. Some cannot imagine dating someone who doesn’t do the same thing they do. Some (me) are horrified by the very thought. It’s kind of a fun split.

      1. The biggest problem with this is what happens if you don’t both get tenure? Or one of you wants to go admin or is in a faculty-adjacent field, and the only way to move up is to MOVE? Which is common, as we do tend to die in the traces. The two-body problem is real… My life would have been much less complicated if one of us was in something portable and non-academic, even though we actually managed to get an almost ideal resolution to this. This time.

  14. His message implied that he was going to ask me out “until he realized who I was,” which made me immediately uncomfortable. Dude, if you realized that, why did you message me anyway and tell me that?

    Yeah, that seems weird to me too, especially in light of dude going on to refuse to take a hint. He clearly understands that many people don’t feel comfortable dating a coworker but seems to be trying to maintain some sort of plausible deniability by not outright asking you if you are interested in dating him. If he had gone on to take a hint and end the conversation I could see that first message as an attempt not to make you feel pressured, but something about hinting that he would date you if you were willing to date a coworker and then refusing to let the conversation drop seems weird and kinda pushy.

    1. Yes. I would take the initial sally as (if OKC still shows “who viewed your profile”) as lampshading “oops, yup, that was I who viewed your profile, haha, small world and we’re squishy meatbags in it, how weird, I am subtly working in reassurances that you come off as fine in your profile in case you’re anxious about that and I am bringing this up because ignoring that it happened might feel creepy and stalker-y, ooh, is that five-layer dip?”

      But… pushing. Dude. Don’t push.

  15. I feel like blocking is too much off the bat. Honesty 1-1 is the best policy. If you aren’t listened to after being direct, then you can consider further steps. There are some people who would be okay with their coworkers wanting to date. So, I don’t think it’s fair to expect the other person to know your intentions from the get-go.

    1. You can absolutely block in a friendly way, with a quick message explaining why.

      It’s a dating site. If you know you don’t want to date someone, being shown their profile repeatedly reduces your chances of seeing profiles of people you may want to date.

      Blocking just helps the site work. No point in _not_ blocking or hiding anyone you know you don’t want to date.

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