Can I suggest my colleague we share a hotel bedroom?
April 24, 2015 10:38 PM   Subscribe

A couple of weeks ago a female coworker I hadn´t had much contact with approached me (male) in a more-friendly-than-usual way and after chatting for a while told me she would be interested in attending a seminar she knew I was attending out of town. She asked me if the two of us could travel together. We did and spent the day together at this event sharing the trips, breaks, and meals.

I sensed she was flirting with me at times, even though she recently told me she has a boyfriend who lives with her. Late at night when I was back at home she texted thanking me for taking her to the event and saying she had had a nice time.I suspect she might be experiencing trouble with her partner, which would partially explain her sudden interest in spending out-of-town time with me (I am, incidentally, the only heterosexual man in her small department at work). There is another related event out of town two weeks from now, and my colleague and I have registered to attend. Since this next event will be two days long, I told my colleague it might be more convenient for us to stay overnight at a hotel in the town where the seminar is being held. She agreed, and I agreed to find out about costs. The thing is that I am attracted to her, and I feel she might have been showing signs of interests toward me. So, the question is: would a fb suggestion to share one room with two single beds (initially, for the sake of money-saving) be too forward? I think it might be a test to see if she is really interested in a more intimate sort of contact.
posted by Basque13 to Human Relations (69 answers total) 2 users marked this as a favorite
would a fb suggestion to share one room with two single beds (initially, for the sake of money-saving) be too forward?

I think so. If she told you that she has a boyfriend who lives with her (and you don't know for certain they have an open relationship) then it's inviting drama to try to get involved with her. And it's definitely more-than-flirting to suggest you share a room. Look at it this way: if she's not interested in you (despite whatever you have perceived) and agrees to share a room, you've put her in a weird situation. If she is into you, then you're not really fooling anyone, though I guess it's a bit more subtle to be all "Oh hey we're saving money!" And if she's into you the fact that you each have a room would not be a hindrance to you getting together though, again, it sounds like maybe a bad idea.

Generally speaking male and female colleagues in general business situations who don't know each other don't share rooms. There are certainly exceptions (and I've shared rooms with male colleagues but never ones that I was maybe sorta attracted to) but that's the rule of thumb. So I would not suggest this. I'd suggest just talking to her "Hey I sort of like you what is the deal with your boyfriend" and doing this in a more open and honest way.
posted by jessamyn at 10:46 PM on April 24, 2015 [22 favorites]

Best answer: Absolutely not appropriate. You must get two hotel rooms. If one of them goes unused, which is possible (but not advisable - that's a whole other mefi question) then the money lost will be worth it compared to the price you'd probably pay in dignity and reputation for suggesting you share a room. Just, no!
posted by hazyjane at 10:47 PM on April 24, 2015 [128 favorites]

No. Get two separate rooms and don't suggest otherwise. It is easy enough to end up in the same room if both of you really want to hook up.

....although honestly, even if it turns out she does want to, hoping to hook up is probably not a wise idea. She has a live-in boyfriend, she is your colleague, and her "flirtation" may well be just her being nice.

Just be pleasant and professional and play it cool.
posted by aka burlap at 10:47 PM on April 24, 2015 [18 favorites]

No. Leaving aside the issue of whether or not it's a good idea for you to get romantically involved with your co-worker who would be cheating on her partner, you do not want to be stuck in the same room together if one or both of you becomes uncomfortable with the situation at any point. Hang out in the hotel bar, or even in one of your rooms if you must, but you should each have a room of your own to retire to.
posted by mbrubeck at 10:49 PM on April 24, 2015 [11 favorites]

There are very few circumstances in which opposite gender coworkers sharing hotel rooms for work-related events is appropriate. This is 129% not among them.

Even if the two of you end up sleeping together before this trip, you should have separate rooms at this event.
posted by jacquilynne at 10:49 PM on April 24, 2015 [18 favorites]

No, this is really creepy no matter how you spin it. Two rooms, communicate clearly. Even if one room goes unused for some portion of the trip, nothing you get up to would make having some private space for each of you a bad idea. Even if it's just for her to have a place to make some private phone calls or whatever. Either way you need two rooms. If it's a matter of expense, is work paying for these trips? That makes it even creepier imo to suggest getting one room.

If you want to gauge her interest in you and her current relationship status, ask her with words.
posted by Mizu at 10:51 PM on April 24, 2015 [12 favorites]

No, not appropriate.

Don't get me wrong - if you want to pursue a relationship (or fling) with this woman, by all means. All signs point to her being into you. But this is a weird boundary-crossing way of trying to tease information out of her. I agree with others suggesting more direct and honest communication.
posted by O9scar at 10:56 PM on April 24, 2015 [1 favorite]

Response by poster: is work paying for these trips?
No. Even though the seminar is on an issue related to our profession, attending was my own idea. I am paying for all my expenses. So is my coworker for hers.
posted by Basque13 at 11:01 PM on April 24, 2015

For the love of god, no.

This is a surefire way to kill any interest she might have in you.
posted by Tamanna at 11:16 PM on April 24, 2015 [6 favorites]

posted by Eyebrows McGee at 11:26 PM on April 24, 2015 [38 favorites]

Tamanna's right. Setting aside the dubiousness of asking her (morally, professionally) and looking at this only from a pragmatic point of view, it's against your self-interest to suggest this. It's moving a million times too fast and if she IS into you but she has a boyfriend she needs to either kick to the kerb (or psych herself up to cheat on if that's what you want) this overly forward move on your behalf will rupture your mutual flirtation. You need to be a bit more gentlemanly here. Play the long game.
posted by stevedawg at 11:31 PM on April 24, 2015 [4 favorites]

Well, if you happen to know what the cost is for one room with two single beds, then you have the answer if she suggests "saving some money". There's really no way to bring it up though, you have to let her. AND it's a bad idea if you work together.
posted by ctmf at 11:45 PM on April 24, 2015 [2 favorites]

Are you kidding me? No.
posted by mgrrl at 1:24 AM on April 25, 2015 [1 favorite]

Ugh please don't do this. Even though it is completely her responsibility to remain faithful to her partner, testing the waters with her to see if she will cheat on him is a shitty thing for you to do. If you had a live-in girlfriend, how would you feel if a male coworker was trying to get her into bed?

If she's interested in you, hopefully she would pursue you once she is single. Until then, keep your relationship with her professional.
posted by kinddieserzeit at 1:40 AM on April 25, 2015 [4 favorites]

It's a unanimous no.
I don't know how this wasn't already obvious to you.

Take some time to look after your head. Happy, well people don't do this kind of thing.
posted by stellathon at 1:41 AM on April 25, 2015 [18 favorites]

Jesus Christ no.
posted by feckless fecal fear mongering at 1:46 AM on April 25, 2015 [3 favorites]

No, completely inappropriate and likely to kill any possible interest she had in you.

Suggesting getting a hotel room together (which is essentially what you're doing) after going to one professional outing together reminds me of the dudes who send you a dick pic after you've casually answered their first message.
posted by colfax at 1:47 AM on April 25, 2015 [26 favorites]

I mean seriously, this is inappropriate for two reasons, either of which is way more than enough to say no.

1) She is a coworker. Don't shit where you eat. This goes quadruple if you are in any kind of supervisory position, no matter how tenuous.

2) She has told you she has a boyfriend and you do not know for a fact that they have an open relationship.

Stop crossing boundaries and keep work relationships professional.
posted by feckless fecal fear mongering at 1:53 AM on April 25, 2015 [18 favorites]

One of the great things about AskMe is sometimes I'll see an answer that is deeply counterintuitive to my initial thinking. When I think about that response, I can see the sense of it and I like to think that over the years, this community has helped me get into a Devil's Advocate position and I can see many sides to a a situation that I would haven't thought of on my own.

When I try to play Devil's Advocate here, let's say you DO suggest sharing a room, I come up blank.

Dear God, in a million years don't do this. It's wildly unprofessional and somewhat bonkers. Opposite gendered coworkers don't share hotel rooms, ever.
posted by kinetic at 4:40 AM on April 25, 2015 [23 favorites]

Of course not. It's concerns me that you even need to ask, makes me think perhaps you might be misinterpreting some signs as well. Separate rooms, and proceed with extreme caution.

Perfectly OK to offer to book the rooms, and ask if she has any special requirements for hers.
posted by dickasso at 5:15 AM on April 25, 2015

no no no no No No No NO NO NO NONONONONO.

What's with this "plausible deniability" stuff? Why can't you just ask her out? I strongly suspect you are afraid she will turn you down. So, you want a situation in which you two are together in an intimate way - because what's more intimate than changing clothes, brushing teeth, and being asleep? And you are hoping that the pressure of the situation will inspire her to be intimate in other ways too, ways she wouldn't have been had you asked her straight up for a date. Dude. Ew. She doesn't need a push to be attracted to you.

posted by chainsofreedom at 5:27 AM on April 25, 2015 [14 favorites]

Trying to casually sleep with a coworker in a small department is generally a pretty terrible idea. Sleeping with a person in a long-term live-in relationship is generally a pretty terrible idea. Combining these two terrible ideas doesn't make them into a better idea.

Don't shit where you eat. If she breaks up with her boyfriend and moves out, and if the two of you end up in job roles where if this doesn't work out, you won't have to work closely with each other, then maybe consider asking her out on a date. But definitely do not try to have an affair with a non-single coworker on a pseudo-business trip by casually suggesting that you share a room based on your perception that she might be flirting with you.
posted by decathecting at 5:48 AM on April 25, 2015 [5 favorites]

She's a colleague with professional advancement interests. You two get along. She doesn't want to sleep with you.

Proceed under those assumptions and pretend that you think she is a professional person who has her life together and wants to attend a seminar and not have a cheating fling with a colleague. See her as a peer in the workplace and only proceed with this friendship if you can do so professionally. If you come across another out of town event, suggest it to her but do not go yourself. If someone asks about her at work say, "Oh yeah, she is a really smart and driven person, I've been really impressed at her take on things. She should move up the ladder quickly." Never let anyone else at work get a hint of impropriety.
posted by amanda at 6:16 AM on April 25, 2015 [10 favorites]

Yeah, hell no. That suggestion could go sideways really fucking fast.

Two rooms. You may end up using only one. But start with two.
posted by Cool Papa Bell at 6:37 AM on April 25, 2015 [1 favorite]

Every step of this is a bad idea, including having an affair in a small department to pursuing someone who has a live in boyfriend.

But if you are going to go forward with this (which it sounds like you are), don't jump straight to room sharing. Stay with separate rooms and even if you guys hook up you still both have private places to shower, etc, plus full deniability at every step.
posted by Dip Flash at 6:39 AM on April 25, 2015 [1 favorite]

Good Lord, no way, get two rooms and stay professional.
posted by amro at 6:44 AM on April 25, 2015 [3 favorites]

Best answer: Everyone here is being kinda prudish, but straight up suggesting this room share isn't going to work. Try mentioning in person to her, "Man these hotel rooms are expensive huh? Did you get yours yet?" and see what happens. She might suggest cutting costs with one room. If not, nbd. If you like her, and can be chill about it, maybe you guys could get together, but the advice to be cautious is good. Flirting is one thing, actually leaping into an affair or breaking up with her bf is another. Keep in mind she just might want the attention and friendship, and be OK with that if that's the case.
posted by Potomac Avenue at 6:45 AM on April 25, 2015 [3 favorites]

I think it might be a test to see if she is really interested in a more intimate sort of contact.

Ask her out for a drink after work sometime. Either to discuss something further or to unwind.

Don't go the hotel route. That's not a test. That's the real deal.
posted by RainyJay at 6:47 AM on April 25, 2015 [2 favorites]

Even if you guys are going to hook up (which is a bad idea), suggesting that you two share a hotel room is not the way to get there. I'm flabbergasted that you don't already know that.
posted by J. Wilson at 7:04 AM on April 25, 2015 [5 favorites]

I am super-paranoid about the appearance of propriety at work. I cut back on weekend work when a married male colleague came on board and started working weekends- I won't be there alone with him because people will likely talk shit about why our cars are the only two in the lot on a Saturday, and while I am the sort who doesn't really care what people think, my job is stressful enough without layering gossipy bs on top to deal with. And if I were the woman in your question and was going to a conference with a male colleague and had a boyfriend at home, not only would I not share a room with him, but if I thought he was into me, or if I were into him, or if I thought people might think either were the case, I would stay at a different hotel altogether. If you care about this person at all as a human being, you would not put her in such an awkward shitty position to ask something like this or even think it. Your scenario had given no indication of why you think she's flirting or why you would think she would be open to having sex with you other than that she spent time with you at a work-related conference and had her meals with you. Wtf man! That is what colleagues do at conferences! It doesn't mean they want to bone, it means it's too weird or there's not enough time to mingle with other attendees. Unless she's been super forward in a way you omitted, bear in mind that her mention of a live-in might be her way of noting that you are getting flirty and trying to tone it down while staying friendly and professional so as to not compromise her entire fucking career. Bear in mind that for women, we still hear other people voice the shittiest things, like wonder who we fucked for a promotion or allude that our powers of persuasion lie in our face or cleavage or between our legs instead of in our minds, our training or our years of experience. Layer on top of that, we can't be friendly and professional to the only person we know at a conference and then be classy and polite enough to send him a thank-you-text without him assuming we want to fuck him so badly we'd derail our live-in relationship and perhaps our career. Jesus. Just no. Please never put another human being in a situation like this. In the event she is into you, which I'm very sorry to say, but I don't think she is unless there is something you didn't post, she can make a move just as easily if you have two rooms as one. (By which I also mean, don't make a move at this conference.)
posted by mibo at 7:21 AM on April 25, 2015 [63 favorites]


Moral issues asides, even if she did fancy you, a man who would approach me like that is the opposite of sexy. You're basically telling her "You know I'm gonna bang you so let's get straight to the point and save us some money in the process, alright honey?".

Not very charming.
posted by Sijeka at 7:24 AM on April 25, 2015 [20 favorites]

I thought i recognized your screen name. NO. unequivocally, NO. Do NOT make this suggestion. For the excellent reasons everyone has listed above.

This woman is not hitting on you. She told you about the boyfriend because you're apparently not getting her hints that she is not hitting on you. Because you're reading her friendliness as flirtation and she does not want you to do that.

And aside from that, dude. You have GOT to stop pursuing the most inappropriate, unavailable woman who happens to be in your life at any time. You gotta maybe do some work and get to the bottom of why you turn up on AskMe time after time looking for advice on pursuing people that under absolutely no ethical circumstances whatsoever should be pursued by you.
posted by We put our faith in Blast Hardcheese at 8:00 AM on April 25, 2015 [60 favorites]

Look, even if you're right and she actually is coming on to you (which, from your questionable judgement in past AskMes I'm not sure is the case) this would be like jumping to step 10 while skipping steps 1-9. If you're at this conference and she asks you to get drinks after dinner, then mayyyyybe you're at step 2: flirt a little and find out what her actual relationship situation is. Don't try to run before you walk.
posted by MsMolly at 8:23 AM on April 25, 2015 [5 favorites]

Oh, sweetie. No. Just no.

mibo is absolutely right about the propriety thing.

So I'm a lady. Several jobs ago, I discovered my coworkers had assumed I was hooking up on the regular with a male colleague just because we kept similar hours and would walk to the subway together after work. There was nothing there: I literally never saw him alone beyond those ten minutes a day. The people I worked with were otherwise lovely, professional, smart people, and yet they were all super judgmental of me. They had talked about this issue with each other! They freely commented on my integrity. My male coworker received no such judgment or comment. And this was in a large, progressive US city. I was (and still am) astonished.

Women especially have to be careful to avoid any sense of impropriety. So if you like and respect her, don't suggest this.
posted by mochapickle at 8:43 AM on April 25, 2015 [12 favorites]

(a) god no, but just as importantly, (b) she is not interested in you. She told you about her live-in boyfriend as a way of making it super super clear that her friendliness is professional, maybe at best that she's potentially interested in being friends. For god's sake, don't put her in a situation where she's trapped in a strange city with you after shooting you down just because you can't take a completely standard social hint.
posted by you're a kitty! at 10:08 AM on April 25, 2015 [10 favorites]

Absolutely not.

Seconding someone else to get therapy or get help - I am genuinely confused as to how this could be considered an option for you. There are things that are between the lines and are blurred based on society's behavior and asking friends and family helps decides on those ambiguities.

And there are things that are clearly communicated (I assume you work in a standard workplace) as unacceptable behavior.

I am kind of offended, actually, as a woman that you would think this is remotely appropriate to ask a woman with a boyfriend, who has communicated that to you, and a coworker on top of that, that you share a room. At the root of it's disrespectful to her and no consideration towards what she has said.
posted by pando11 at 10:15 AM on April 25, 2015 [10 favorites]

A world of NO. You don't even know that she's interested in you -- what you take for flirting might just be friendliness on her part. Even if she has been flirting with you, that doesn't mean she wants to sleep with you! And just think how incredibly awkward a situation it will be for her if you suggest sharing the room to save money, she takes you at your word that you really only want to save money -- how do you think she'll feel when she discovers that you were actually just hoping to get into her pants? Terrible idea. Don't do it. Just don't.

(I, too, have been in the situation of having people assume I was having an affair with a male coworker -- we were friends, yes, but that was all! We chatted at work a lot, I house-sat for him and his wife once, I spent time at their house socially -- with both of them -- and there was NOTHING romantic going on at all. But still, I found out later that people were gossiping like mad about us, and it SUCKED. You do NOT want to put her in the position of being office gossip-fodder.)
posted by sarcasticah at 10:56 AM on April 25, 2015 [1 favorite]

I'm going to gently, nosily bring up your Ask.Mefi posting history. You seem to have asked the following questions in the past:

- Is it appropriate for me as a 30 year old professor to get romantically involved with an 18 year old student who I taught in a night school for high school drop outs?
- Should I get involved with a woman who has listed on her FB profile that she is in a relationship?
- My coworkers seem to be brushing me off and I don't know why.

I don't know if there's a connection here, but it's your life - Is there a connection? Also, no no no no no no no, don't do that. Ick. I can't imagine how violating this proposition would feel for your coworker.
posted by mermily at 11:12 AM on April 25, 2015 [8 favorites]

This event will go badly for you. I would reconsider attending. At the very least I would find other colleagues to attend along with you both, given that the seminar is related to your field in general.

I understand that you are getting some kind of fix from her friendly attention and entertaining the notion of intimate activities with her, but you have already mentally gone too far -- this will not go well for her OR for you. EVEN IF you do not share a room, she will soon find herself stuck in a position where she has to reject you, to regret/withdraw her collegial behavior, to have her heart broken about a woman's ability to be treated non-sexually in her career... or to be "successfully" preyed upon by you. If indeed she is having trouble with her partner, that is LESS of a reason to try to advance a sexual/romantic relationship with her, not MORE (!!). It means that she is vulnerable. Good people undertand this and do not try to use it to their advantage.

You must get a grip on your attraction to her and erase from your mind the possibility of "intimacy" with her, ever. If it turns out that she IS considering you In That Way, this is MORE true. There is no chance of this proceeding in a way that will not cause turmoil in her life and in both of your jobs. There is absolutely nothing in your post that indicates that you are the love of each other's lives for whom any of this would be remotely worthwhile. Stop it. Now. If you need to limit extracurricular time in her company while you get a grip on your attraction so that you can interact with her respectfully as a colleague, recognize that in yourself, stop rationalizing that you may have a shot at her and that such a hypothetical shot is worth the damage you will cause or, frankly, worth even wasting your mental time on her instead of a much, much more suitable potential partner who is (A) single and (B) not a co-worker.

Please don't let any thought of "Oh, but those MeFites don't really understand how she was looking/talking to me, and our workplace is actually pretty chill, and I woudln't have to work with her directly if an affair/relationship goes badly" convince you that our unanimous advice is wrong. Your inability to understand it should be a red flag to yourself, and you should care about yourself enough to want to benefit -- for your own good!! -- from working with a trained professional to unlock it. Let them prove us wrong if that's really the case.

I wish you the best of luck. Meanwhile, please, for the love of any god, leave this woman alone.
posted by argonauta at 11:31 AM on April 25, 2015 [8 favorites]

Following on from argonauta, I'd like to point out that such emphatic unanimity is really, really rare on AskMe.
posted by feckless fecal fear mongering at 11:35 AM on April 25, 2015 [10 favorites]

Following on from argonauta, I'd like to point out that such emphatic unanimity is really, really rare on AskMe.

Holy crap, that's totally true. You could ask about the ethics of handing out free hundred dollar bills and get more disagreement than you're seeing getting here.
posted by Cool Papa Bell at 12:09 PM on April 25, 2015 [10 favorites]

My impression is that you have a history of thinking that women who are talking with you for work-related reasons are possibly flirting with you and potential date material when they probably aren't. I suggest from here forward you try to err strongly on the side of assuming women you meet in some kind of work-related context are just talking to you for work-related reasons and not because they want to hook up with you.

Unless this woman tries to drag you off to bed, I think you should assume you have been friend-zoned and she is being all chatty and relaxed BECAUSE she doesn't think of you that way. Your life will go better if you stop assuming that every woman who is nice to you for 3 nanoseconds wants to jump your bones. That is usually what men are thinking. It is usually not what women are thinking.
posted by Michele in California at 1:12 PM on April 25, 2015 [10 favorites]

In case you need another voice to add to the chorus: no. There is no circumstance under which this would be appropriate. It would not be appropriate even if she suggested it; it would not be appropriate even if you were already actively having an affair. There is no sign here that she is interested in having an affair with you. Given that the two of you are colleagues, a romantic relationship is incredibly inadvisable under any circumstances. Given that she is in a long-term partnership, it would be beyond gauche for you to approach her with the idea of starting an affair. In short, every single aspect of this is a titanically objectionable idea even when considered separately. Taken together, it approaches Sharknado levels of bad idea.
posted by KathrynT at 3:47 PM on April 25, 2015 [4 favorites]

Everyone here is being kinda prudish, but straight up suggesting this room share isn't going to work.

Yeah, I am a little surprised at the number of "no mixed-sex roommates" answers (and it's occasionally come up at work) -- the specific gender, sexual orientation, and/or availability of your roommate is irrelevant as long as what you have is a professional relationship.

In my professional career, I have had a rotating cast of 3 regular roommates for meetings -- two women and one man (I'm a man). The only reason any of these worked is that I had no romantic interest in any of them; while we are friendly (chatting or emailing relatively frequently and getting together for a drink when our paths cross), my relationship with each is largely professional. Hooking up is not on anyone's agenda.

Additionally, outside of work, I have an ex who comes to visit me from another city about once a year and who shares a room with me at a convention. That situation works because the ex, the ex's husband, and I all understand that, while we are old friends, we are not romantically inclined toward each other and nothing of a romantic or sexual nature is going to happen.

Any of these roommate situations would go quickly bad if sex entered the picture, and I am of an age where maintaining productive professional relationships and old friendships is much more attractive than a quick fling (followed, almost certainly by drama and regret). This is part of being an adult and having adult relationships.

tl;dr -- it is possible to have healthy roommate relations with colleagues, but only when everyone's motives are completely clear and "above board." The situation you are describing is likely, at best, leave you frustrated and embarrassed, and, at worst, cost you your colleague's respect and friendship (and, not unlikely, your general colleagues' respect and friendship). It's not worth it; not for you and certainly not for this woman.
posted by GenjiandProust at 3:54 PM on April 25, 2015 [4 favorites]

I started off thinking against the grain here*, but the later comments here changed my mind. It's pretty clear this is an issue that has come up several times for you and it appears you have difficulty reading the intentions of women you find attractive (so do I, but usually the other way - apparently I'm oblivious to actual interest in me).

Unless she has been absolutely unequivocal in expressing her desire to take things beyond a professional friendship, don't even think about or hope for anything more. By 'unequivocal' I mean she actually needs to say something very close to 'I want to fuck you'. With actual words, not just your perception of her behaviour. The overwhelmingly most likely scenario is that she is interested in being 'work friends' and absolutely nothing more. That she would agree to share a hotel room is almost certainly because she doesn't desire you in any way and (this part is important) has no idea that you feel this way about her. If she had any desire for you or was at all interested in you or thought you felt this way, she would be far less likely to be interested in sharing a room.

Don't do this - it will most likely put both of you in a horrible situation. Your apparent propensity for mis-reading social situations (one I sympathise with a great deal, as someone who is largely socially clueless) dramatically increases the risk of things going horribly wrong.

*because I don't think there's anything wrong with colleagues sharing a hotel room if they get on well and it doesn't have to mean anything beyond saving money. I also don't think there's anything intrinsically wrong with romantic relationships between co-workers, although it's rather risky in many situations. I'm aware this is not the prevailing view on both counts and am also a bit surprised at the prudish nature of many comments here.
posted by dg at 4:00 PM on April 25, 2015 [5 favorites]

Response by poster: Get two separate rooms and don't suggest otherwise. It is easy enough to end up in the same room if both of you really want to hook up.
That's the sort of level-headed and hysteria-free observation I was seeking. I'll move ahead along those lines. The 2 of us will most likely have a private dinner together once we leave the conference. By bedtime, I guess it will already have become clear whether we'll share a room or not.
posted by Basque13 at 4:04 PM on April 25, 2015

The thing is that I am attracted to her, and I feel she might have been showing signs of interests toward me.

Your attraction to her is clouding your objectivity. She's being nice and friendly, as colleagues often are to one another. You work together, so you attend work-related events together. Overnight accommodations are a practical consideration for a weekend-long work event. This all makes perfect sense in the context of work. But you are taking these cues out of context, and reading them as flirtation. Because you're attracted to her, and you want her to be attracted to you too. This is a pattern in your AskMe questions.

I know suggestions have been made under your previous questions for you to go to therapy and gain a better understanding of your interactions and relationships with women. Have you? You really, really should. You're still young and have time to figure this out, but it doesn't seem like you're making much progress on your own. And you've got to stop viewing the women at your workplace as a dating pool. Even men with plenty of dating experience and social accumen need to be careful when mixing work with romance. You are almost guaranteed to make a huge mess of things if you try dipping your pen in the company ink. Just DON'T. The fact that you view answers that don't play into your fantasy narratives as "hysteria" is pretty concerning as well.

So, the question is: would a fb suggestion to share one room with two single beds (initially, for the sake of money-saving) be too forward? I think it might be a test to see if she is really interested in a more intimate sort of contact.

First of all, this is absolutely the worst idea. Even if she is into you, going about it this way is so incredibly disrespectful and tasteless. Too forward? More like totally vulgar and offensive. So much so that I'm going to say, on her behalf, that any budding attraction she might feel toward you would be doused out by such a question. Like, "Hey, I know you have a serious boyfriend and all, but I want a piece of that. I know I could use my grown-up words and express my feelings in a way that might preserve some shred of our professional relationship and mutual dignity. But I'm really most interested in shielding my fragile ego under the guise of convenience and frugality, and also the assumption that you're easy and have no respect for your boyfriend (all things a woman really wants to hear whilst being propositioned). Whaddaya say, wanna bang?"

And don't "test" women - if there is something you want to know, ask them. If you are too afraid of the answer to ask the question, then maybe you don't deserve to know.
posted by keep it under cover at 4:06 PM on April 25, 2015 [13 favorites]

Basque13: "That's the sort of level-headed and hysteria-free observation I was seeking. I'll move ahead along those lines. The 2 of us will most likely have a private dinner together once we leave the conference. By bedtime, I guess it will already have become clear whether we'll share a room or not."

This is ringing all sorts of alarm bells for me, even as the person who thinks it's generally OK to share a room with a colleague and that romantic workplace relationships are not automatically bad. Despite all the advice to the contrary (advice you ASKED FOR because you weren't sure this was a good idea), in your mind, you're just blindly moving ahead with your plan and cherry-picking one comment you perceive as saying 'go for it, dude' among a wall of comments saying 'bad idea' to justify it. If you're just going to ignore the advice, why did you bother asking for it?

It seems clear that you have laid out a plan of attack aimed at getting into the pants of a woman whom all signs say is not interested in you. If you go ahead with this, you better hope she's generous enough not to bring down the consequences of your plan on your head when it almost inevitably goes horribly wrong.
posted by dg at 4:50 PM on April 25, 2015 [33 favorites]

Not only should you not do this, but you should seriously consider the consequences of this blowing up in your face. Like, getting reported for sexual harassment and fired because you're doing this with a coworker at a work related function. The only mitigating thing you have on your side is that your work isn't paying for the hotel, and that's pretty flimsy.

I have seen people get in serious trouble with their school or work for a lot less.

I am not one to hysterically overreact. I'm also not someone whose automatically against doing stuff with a coworker, and also someone who thinks it's the responsibility of the person in the relationship to cheat or not cheat.

I just think this is a really bad idea because even disregarding the(imo legitimate but, just for the sake of conversation) points above about this being gross... you are opening yourself up to serious risk here by thinking with your dick like a high school kid trying to get it on in the drama room closet.

And even then, the shameful fuckers i know who would smoothly pull off this kind of thing would always get their own room, and it would just be a thing that "randomly happened!". The air of plausible deniability and MTV-ad-style by chance quality of the whole endeavor.

You shouldn't do this because even ignoring that it's an awful idea for other reasons, it wont work. And you could also get in serious fucking trouble with your employer.

And yea, i could seriously rant about the whole "hurr durr of course she wants to fuck me" thing, but i didn't even have the energy to go there.

Oh, and i have to second this having more consensus than a "my house is on fire, should i call 911?" question would have.
posted by emptythought at 5:01 PM on April 25, 2015 [10 favorites]

Do you want this woman to want to speak to you again? Are you interested in being friends with her other than the possibility of her sleeping with you?

Because being creepy at a conference is a good way for her to just decide to fade out in the future. And your update:
The 2 of us will most likely have a private dinner together once we leave the conference. By bedtime, I guess it will already have become clear whether we'll share a room or not.
is super-creepy.

I mean, dude, women should get to socialize with their male colleagues at a conference without the assumption that the only reason they want to spend time with the male colleagues is because they're interested in sex.

Nothing you described about the interactions at the first seminar sound like she's interested in you.

It sounds like she was polite, and friendly. Polite and friendly does not equal "want to have sex with you".

"Wants to go to career-related seminars" does not equal "problems with her partner".
posted by leahwrenn at 5:17 PM on April 25, 2015 [18 favorites]

You're just barreling ahead into a situation that's going to make this woman feel totally grossed out and disrespected. Just FYI.
posted by you're a kitty! at 5:17 PM on April 25, 2015 [16 favorites]

I didn't add this in my post, but you're a kitty! brings up a point that made me realize...

What you're planning on doing here, even in the update, is exactly the kind of thing a friend of mine would tell me over beers in an ugh-what-do-i-do-now sort of tone. If you do this and it backfires like it will, then she's effectively trapped at the conference with you having it be awkward as fuck for the rest of it. Even if she has her own room, she still has to see you every day and fly back with you and interact with you normally and "professionally" after you've made shit awkward as fuck.

You won't really have to own it, is the fucked up part. It'll all be on her.

I think you need to own now how terrible you could make this for her, and how she'll feel like there's nothing she can really do until it's over once it happens.

Creating that kind of situation is something the shittiest creepy people do.
posted by emptythought at 5:32 PM on April 25, 2015 [29 favorites]

That's the sort of level-headed and hysteria-free observation I was seeking. I'll move ahead along those lines. The 2 of us will most likely have a private dinner together once we leave the conference. By bedtime, I guess it will already have become clear whether we'll share a room or not.

Oh, COME ON, dude. Of course this is the comment you like. I remember your screen name; I rolled my eyes as soon as I saw it come up and knew it would probably be another one about an unavailable woman (either co-worker or student, probably in a relationship) who hasn't actually expressed interest in you, but around whom you've already built plans and fantasies. Please, please listen to the MeFites who are telling you they see a pattern in your questions, and talk to a therapist about the way you relate to women. We're not being hysterical (what are the chances that every single response but one is from a "hysterical" person?); we just recognize your type from other places in our lives and are trying to steer you away from being the creepy guy women try to avoid. I know you've seen therapists before, but I think you need to tell one that your presenting problem is you can't differentiate appropriate crush material from inappropriate crush material and would like to find a way to stop looking for a girlfriend in every woman you meet.
posted by Yoko Ono's Advice Column at 8:28 PM on April 25, 2015 [16 favorites]

Also I notice one of your tags is "reboundrelationship." She has a live-in boyfriend and there's no confirmation she wants to end that relationship, so I mean, you're not even putting the cart before the horse here. You're putting the cart in another time zone from the horse.
posted by Yoko Ono's Advice Column at 9:09 PM on April 25, 2015 [13 favorites]

Just to drive home (one more time) the consequences you're looking at: if I were your coworker, I would have zero reservations about disclosing to my friends, our mutual colleagues, and our boss my upset about how "I agreed to go with Basque13 to a conference to further my professional development, and based on the fact I was friendly about spending time with him one on one at a different professional event, he actually called me to ask if I wanted to 'save expenses' on sharing a single hotel room, even though he knows I have a live in partner."

You will never, ever wash off the taint of "creep" ever again at this workplace or within the same social circle, if there is ever any overlap outside of work. And in many workplaces, this could additionally be written up as sexual harassment.
posted by blue suede stockings at 10:02 PM on April 25, 2015 [12 favorites]

Here's yet another way to think about this situation: by telling you outright that she has a boyfriend (double points for living together) (triple points for saying so to someone who is a coworker)--without any explicit qualification of "but it's effectively over" or "but we have an open relationship" or "but I can't help finding you wildly attractive"--she knows that a reasonable listener will therefore consider her unavailable. Off-limits. If somehow that it is actually NOT her desire or intention for you to assume that, she knows that the onus is 100% on her to initiate any kind of intimate activity. She would not use subtle "maybe-he'll-sense-that-I'm-maybe-flirting-at-times."

Are you truly unable to have a level-headed and hysteria-free ability to put yourself in her shoes and see this? To grok that NOTHING in her behavior suggests that sexual overtures or feelings from you are welcome or invited, and how awful it will be for her (and, at best, fruitless for you) to misjudge this? This is not an insult, from her or from the commenters here, nor some prudish quashing of your potential fun -- it is simply a straightforward, rational truth about how adults interact with one another, especially in a professional setting, plus first-hand knowledge of how truly badly things go down when what someone is telling you is discarded in favor of your entirely self-centered desires and intentions.

I am relieved that you seem to have decided against suggesting a shared room. I am troubled that you still do not see how wrong it is to approach this event, that dinner, this person, primarily as an opportunity to get laid -- and that you do not see (or care about) the grim likely outcomes if anything but that happens between you two.

I have no agenda in saying this other a genuine desire to try to help you avoid disappointment, difficulty, and harm. I've shared rooms platonically with coworkers, I've had sex with coworkers, I've had rebound relationships, and I've been in open relationships -- and I am telling you straight-up that this woman does not want these things from you, that it's understandable but wrong to consider or approach her for any of those things, and that for your good AND hers you need to drop it, now. Your apparently sneering dismissal of the risks being pointed out here ("hysteria?" really?) makes it seem all the more likely that your urges are eclipsing your ability to rationally assess this situation and/or any of the consequences as you play out the steps ahead.

Please give our advice some additional consideration.
posted by argonauta at 10:38 PM on April 25, 2015 [11 favorites]

I sensed she was flirting with me at times, even though she recently told me she has a boyfriend who lives with her. Late at night when I was back at home she texted thanking me for taking her to the event and saying she had had a nice time.

One final thing: I--as well as any other woman--cannot tell you how many times since puberty a man I have had zero (or even negative) sexual interest in/attraction to has been utterly convinced I am "into him," "flirting," or "totally sending him signals" just because I have been kind.

I mean, men old enough to be my father I had felt "safe" with because I thought it was clear any time we were spending was strictly platonic mentorship or "like a non-creepy uncle" time; men I literally had to be pleasant with because I was in a co-worker or service industry relationship with; men I found hugely physically unattractive and intellectually stultifying and had absolutely nothing in common with, to the point that a stranger on the street wouldn't have paired me with as a plausible happy match, but whom I had been casually friendly to when other women might not have been, etc. These were men convinced I was sexually open to them (and sometimes pulled things like you are contemplating) to the point where they felt betrayal and actual rage when their propositions were rejected.

All I'm saying is, testosterone and feelings of attraction--particularly if you've been lonely or intensely looking for a girlfriend without the results you want--is a hell of a drug, with regards to reality perception. Do you have any male peers or father figures you can reality check with on this once and awhile?
posted by blue suede stockings at 4:29 AM on April 26, 2015 [20 favorites]

The 2 of us will most likely have a private dinner together once we leave the conference. By bedtime, I guess it will already have become clear whether we'll share a room or not.

I'm confused. This is pretty much text book sexual harassment. How is this not obvious? You've invited your female colleague to a work event with the specific aim of getting her alone to try and have sex with her. Sure, you're not going to straight up jump her, but that's still your end goal here and she won't know about that until it's too late. There is nothing professional or acceptable about this, it's just flat out predatory and wrong.

If you want to go out with her then just ask her out on a date. I'm not some kind of prude, I don't think there's anything wrong with dating colleagues (as long as it's kept out of work) and it's up to her to decide what's up with her boyfriend. But you need to be up front and open about what you want and to move it out of the professional arena. Right now you're not doing either of these things and that's never a good way to start any kind of relationship even without the whole work place harassment angle thrown in.

This is such an easy situation to solve - just ask her out like an adult. The only reason I can think of why you wouldn't do that is you think she'll say no, in which case the whole getting her alone at a conference thing instead is extra icky.
posted by shelleycat at 4:42 AM on April 26, 2015 [19 favorites]

The 2 of us will most likely have a private dinner together once we leave the conference. By bedtime, I guess it will already have become clear whether we'll share a room or not.

What? No.

When someone says they are in a relationship, they are saying "I am not available for you to be interested in and I am not interested in you." Period. Leave. Her. Alone.
posted by feckless fecal fear mongering at 6:25 AM on April 26, 2015 [10 favorites]

Have you considered the practical reasons for not sharing a room? For my part, I would never share a room with a coworker. Propriety aside, I want a place where I can brush my teeth and do my hair and remove my makeup and even - heaven forbid - make noises in the bathroom without an audience. No way in hell am I going to let people I work with witness that. Especially if, hypothetically, they were someone I wanted to hook up with. Why would I abandon the mystique? And why would you want to put that weird pressure on this situation, even if you are reading it correctly?

You're not thinking this through. Consider also that if you haven't thought of these very simple logistical issues, you might not be giving due credit to the very valid points every other commenter in this thread has raised.
posted by AV at 6:46 AM on April 26, 2015 [4 favorites]

I'm going to say no. I'm also going to nth that, whatever you think is going on, there is a 99.99% chance that she is not flirting with you.

I was on the periphery of a situation like this recently and it was unpleasant for everyone involved. Please don't make things worse than they have to be.
posted by daisyk at 9:51 AM on April 26, 2015 [1 favorite]

I'm a woman professional. I travel often for my job and go to a few conferences a year, and my male colleagues often also attend. I am comfortable with my colleagues and don't think of any of them as creepy, but if a male colleague asked me to share a room I would go to my boss and report sexual harassment.

That you are planning to isolate her and hit on her at or around a work event away from home is predatory. Please stop trying to tell yourself that it's okay.
posted by bile and syntax at 12:39 PM on April 26, 2015 [15 favorites]

This is your idea of a test to see if she'd be amiable to more intimate contact? Are you nuts? Are you from another culture? I can see this happening in France, unfortunately. But this is so far from appropriate in the US please don't do this.
posted by lillian.elmtree at 1:11 PM on April 26, 2015 [1 favorite]

Are you from another culture?

I suspect he is, but I am not really clear what other culture would see this as acceptable (ignored and allowed, yes, but acceptable no). Most cultures give at least lip service to discouraging sexual predation.
posted by GenjiandProust at 1:45 PM on April 26, 2015

Please don't go to this seminar with her. The 'get one hotel room' is just the cherry on the whip cream in this bad idea dessert. Your intentions are extremely disrespectful and predatory.
posted by destructive cactus at 2:39 PM on April 26, 2015 [7 favorites]

I'm a woman. I'm a pretty forward woman in terms of being direct and not coy in all forms of communication. I am routinely misinterpreted by men I am looking to network with as someone sexually available. If I am talking to a man in the course of him doing his job or otherwise networking, no, I am not looking for sex.

Even if a sexual relationship is not simply out of the question between us, NO, I am not using work as some excuse to flirt. Men like you make me crazy. And I don't mean that in any kind of positive way. I mean I am so incredibly frustrated and angry about how often I try to discuss work with a man and he turns it into a sexual/emotional/personal thing.

I am HOMELESS and men in positions to help me professionally STILL think the only goddamn reason I would talk to them is to fuck them. NO. I would like to get my sorry ass off the goddamn streets. If you have money, power and influence, your cock is not what I am drooling over here. Your professional expertise, connections, and know-how are what I am after. (I am celibate for medical reasons. I have been for nearly a decade. I am extremely open about that. Men still think I am talking to them to fuck them. I would like to slap a few of these men until my hand is blistered.)

I think you are making a really huge mistake here and if she finds out you planned this in advance, planned it so thoroughly that you even asked questions on a public forum about the best way to try to basically corner her and try to bed her, this could well destroy your career.

Even bringing up the possibility of attraction is a very delicate matter when you work together OR are in an existing relationship. She has both things going on. This has bad idea and terrible misunderstanding written all over it.

Please consider cancelling on her entirely. If you really want to sleep with her, that is the high road. Don't go at all. That may open the door to letting her know you have a conflict of interest here and it wouldn't be appropriate because of that. Going with this skeevy agenda to try to maneuver her, yeah, you are just barely short of being a flat out sexual predator here.

Be advised that I am routinely accused of being a rape apologist for being too sympathetic to the fact that there are two sides to any story and men are just human and so on. And I think what you are doing is barely short of conspiracy to commit rape. Please back out of this entirely.
posted by Michele in California at 3:03 PM on April 26, 2015 [2 favorites]

I kind of can't believe that I feel the need to defend my non-prudishness on Mefi, but it seems to be a point of contention here. I'm not a prude. I'm very forward with men in terms of my sexual interest, just ask my husband how we hooked up. I work in an office that is 85-90% male, and our office culture is very close knit and social. Going out to bars and clubs with my male colleagues is no biggie. If my male manager and I travel together for work, we get breakfast and dinner together. We give each other car rides home, to run errands, etc.

The only reason this works, and that I feel 100% safe with my colleagues and manager and am able to work well with them after mixing work and play, is that I am certain they aren't about to try anything with me. But there are a number of men at my office that I've put up my guard against, because despite me being clear about my marital status, they started taking certain liberties (why? I'm nice and friendly to everyone, and apparently that means I'm DTF right?) Getting touchy feely, forcing sexual innuendo into our conversations, and more subtle clues that only other women would understand - after spending a lifetime as an object of male sexual attention, women's spidey senses become pretty finely attuned. Men with intentions think they're being smooth? OBVIOUS. Think they're being perfect gentlemen? OBVIOUS. Think they're disguising their attraction as friendly interest? OBVIOUS.

OP, just look at how ham-handed your original idea was. If you think you're going to fly under the radar with a more subtle approach, you're absolutely wrong. Unless she is very young or very inexperienced (which would make your new plan all the more creepy), she will know exactly what you're after. For most of my 20's when this happened to me, I was confused and sad. I felt bad that I wasn't worth a man's time or attention unless he thought he was going to get something sexual out of me, whether actual sex, or some jollies and an ego boost. Since I've grown up and gotten used to it, it just makes me angry. It pisses me off that I can be as clear as possible that I am married and not open to this sort of thing, and at work no less, and certain men still feel that their sexual desire deserves to be put first. Don't do this to her. Work on yourself and you won't need to resort to weird stealth tactics to get time alone with a woman.
posted by keep it under cover at 7:43 PM on April 26, 2015 [16 favorites]

Two or three out of dozens of posts were cautiously gently negative, dozens were 'seriously, all sorts of bad idea'

Erica Jong: Advice is what we ask for when we already know the answer but wish we didn't
posted by Jacen at 12:07 PM on April 27, 2015 [2 favorites]

Dude-bro to dude-bro, that is the most un-smooth idea I've ever heard.
posted by whuppy at 2:38 PM on April 27, 2015 [3 favorites]

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