How to tell a coworker that you would like to date them?

Question

I think I'm in an intricate and precarious May-June/May-July situation.

A woman colleague, let's call her Mary, seems to have a crush on me.

She has:

• clung to my arm while walking,
• tried to coyly sit right beside me in the corner at the company group meal,
• asked me if I like her or if I would be interested in older women,
• fawned over the young guy sitting behind me, like patting his head whenever I could catch a glimpse of the two, possibly in an attempt to make me jealous while also revealing something about herself,
• asked me a "what do you see" question that analyzes the personalities of the test takers, going over the positive aspects and agreeing with most of them except "good at expressing one's innermost feelings",

and she did all of the above in the presence of several coworkers and a C-level executive, who I'll call Eric.

Mary works at site A, sometimes visiting site B where I work as she oversees the project that I have been part of. Now I've been reassigned by Eric to work on a new project full-time, and I would be sitting behind Mary. He hasn't told me the details of the new project, just that they needed me, a rather inexperienced newcomer, to "put off fire", and if I remember correctly, he also jokingly said something along the lines of "I'm finding it hard to manage Mary, please help me".

Also, today I asked Eric if I could take a day off (so I could seek professional help from here, though I didn't give him a reason), to which he promptly and gladly granted permission, adding a "wish you good luck" at the end of the message. I find this highly unusual and amusing.

As amusing as this situation might be for reminiscence, I'm really anxious and feel that I, an introverted Chinese male dullard in his late twenties with virtually zero dating/life experience, lack so many necessary skills to properly reciprocate the affection of such a fine lady. I'm also wary of the effect on productivity whether this relationship works out or not, not to mention possible gossips and hard feelings from coworkers. And there's still the possibility that everything is just my wishful thinking, a setup for entertainment or just a means to lighten up the mood.

Going by the statistics, an office romance where the woman is older and has a higher education level than the man rarely ends well, though none of these really concerns the naive me now.

So far I have mostly been a bit cold and avoidant with her, i.e. no idle chit-chat, unless guided by Eric or initiated by Mary. I initially didn't have strong feelings for her and when I realized I do, still wanted to avoid office romance and remain "professional", but it is getting increasingly harder and inhumane to continue this route.

This seems to upset her sometimes. On the other hand, on the most recent account, I decided I couldn't concentrate anymore when she sighed after a short silence and came over to chat with the guy behind me, so I turned my body facing them and listened to their conversation, which quickly shifted towards me and I could see she was more talkative, playful and radiant for the rest of that day (don't know if it's a conscious effort on her part or not, but she also looked more appealing almost exactly a month ago).

I've heard from either Mary herself or a colleague, that she isn't married yet and doesn't seem to want me to have an impression that she is "boisterous". I've also heard people ask about her boyfriend, but I don't know the details.

Question

I would like to tread carefully to get on her good side and not upset or disappoint her if possible. So, how do I tell Mary that I like her and ask her to go out with me without getting permanently awkward or sounding creepy?

Answer 1

The age difference is not the problem. The problem is that you are being positioned to have an in-office affair with a woman that is related to others in power.

First, find out if it is part of a pattern. It is unlikely that you are the first of Mary's interests. It's even more odd that a company would "help" her be "managed" by arranging close proximity of potential sexual relations. Odds are she has more power than you estimate, and if you can see what happened to the others she has had interest in before you, you'll probably find out what will happen to you (and how long it will take) there. Hint: You're not going to be somehow different, so don't trust in your optimism that it will go better for you.

Then, if you decide (against better judgement) to play such a game, just remember that she's managed to get you transferred to her team (indirectly, but she still managed it) and that when things go badly, they'll go really badly. Odds are you will be the one that leaves in a bad way, as if they were going to get rid of her, they would have done it by now. Relationships are harder to form with such imbalances of power, and without care, generally are formed in unhealthy ways.

As for professionalism, she's perfectly happy not being professional about it, if she's perfectly happy carrying on in the workplace as you describe. Asking her to become professional about it is asking her for something that she's not doing, and likely doesn't value doing.

After reviewing all of these concerns, if you still want to ask her out, at least you'll have a better picture of what you are in for. It is easy to dream up successful scenarios, but you should really weigh the costs of unsuccessful scenarios with the likely hood they will happen. You don't want to be the guy that got his promotions due to who he's sleeping with, and then got fired for the same thing (after she's had her fun).

And Eric doesn't have your back. His "put off fire" is "make Mary so busy she can't disrupt the others on the team". He thinks you'll do it for the sex, but that's not a way for you to build a reputation as a person who gets projects done.

To explain the "related to others in power." Let's say you see a pretty girl, do you think you can talk your manager into getting her assigned to your project for the primary purpose of dating her? I would think no, so whatever she's got, it is a strong relationship (not necessarily a healthy one) with those in power. Do you think you could even get a seating arrangement near a girl of your choice? Probably not.

How to play your way out of this situation? Be clueless and hopeless. You said you have very little experience, so use the lack of experience to make her tire of you being a doof. If she flirts with you, panic. If she makes eyes with you, fail to notice. Eventually she'll find her next target, and you'll get a bit of breathing room.

Answer 2

Well she gave you a lot of positive sign. The only "problem" is the professional environment. If you want to have a romantic relationship with her, you should try to develop it outside of work. You just need one action to extract her (and you) outside of this context : simply ask her for a drink, one evening, just both of you. Looking at what you said she'll understand. In doing that, you can : - just develop your relationship in the right context, which is your goal - give her a simple , drama-free way to reject your offer

If she reject you, there shouldn't be any awkwardness/creepyness after that since nothing was explicit . That's the key here, you just use "standard" code of conduct to make yourself clear without being awkward. Just take it as it is and let go.

If she does not, just go to the pub (or whatever you chose) with her, there's a lot of chance that you'll be successful in what you seek, given her behavior with her until now. Even if not, this is now an extra professional relationship, so there should be no embarrassment either.

I won't try to discourage you in doing so. Work relationship can give you a lot of problems, but that's not your question and it really depends of you, her, and the workplace. If it can go well, and if you want to try your chance, I think you should just go and I hope everything will be alright.

Answer 3

First off, in the office romances have a problem. A lot of relationships don't work, but when it's a person at your place of employment, the aftermath becomes very uncomfortable and potentially job threatening. Employers don't like this because it's an unnecessary interference with what the employees are supposed to be doing. Harsh words after a breakup are not uncommon. Harsh words after a breakup in the workplace have serious consequences.

Your boss Eric also threw you a clue: "I'm finding it hard to manage Mary". Uh, in what regard? That's not a good sign. You also have to wonder why he's putting you near her, when he probably knows about her behavior towards you. Maybe she's been coming on to him, too, and he just wants her attention diverted elsewhere.

Now, for some experience I learned the hard way. I don't know that it applies to your situation, but suspect that it might.

Like a lot of software developers, I was socially awkward in my college and early employment years. The idea of actually telling a woman I was very interested in her scared me to death. (She might say no thanks... how awful) My curse was that I must not have been a bad looking fellow, because I had more than one sharp looking young lady throw herself at me in a manner similar to what you describe. It was very flattering, at first. It was also emotionally easy... I didn't have to do anything, didn't have to run the chance I would be rejected. She was doing all the pursuing, and not wasting any time.

Problem was, after a few months, they threw themself at someone else. Happened three times in a row. Naive me thought 'this was serious', and all of the sudden, that great attention I was getting, started going to someone else. That's what some people do, just move from one person to the next. Your job is to weed them out, so you don't get your feelings all munged up... like I did.

This is not a matter of a woman 'being aggressive', but how quickly she's being aggressive, when she probably doesn't know you all that well. It is quite possible she's doing it for reasons other than those that make for a long lasting relationship... you share a lot in common, or you have long discussions about anything and don't want to stop conversing.

Same holds true for men: women I know have told me that men who get overly aggressive very quickly are usually just after quick sex, or they're compensating for strong personal insecurity. Neither of those situations makes for a happy long term relationship.

For all you know, she might be going through a midlife crisis, or having a 'cougar moment', and you're her equivalent of a middle aged man buying a BMW M3.

Without knowing the individuals involved, just the actions, I see a very familiar pattern of behavior that I have lived through. No matter what it might seem like right now, there is a possibility that this won't last, and it can go sour for reasons that you have no control over. (I'm bored with this one, let's go find another) Just as it doesn't matter what you do, she's interested in you now, it won't matter what you do if she loses interest. She's still going to leave.

Be careful letting yourself get attached to someone you don't know all that well, just because she's showering you with attention. It has been my experience that she may end up showering someone else with all that attention, in the near future.

If you want to be happy with a person, you'll have to do what I had to do: get over that nervousness, look for elements of commonality in the person you're interested in, and work up the nerve to ask her if you two can meet after work. And just go have a good time, without being forward, and see where that leads you. When I did that, I met a wonderful woman that I shared a lot in common with, and she was a knockout beauty, too. I was the one guy at a boring party that wasn't overtly hitting on her, we found that we shared a love of dry British humor, and as I left, she insisted that I take her phone number and call her to resume our interesting discussion.

We just celebrated our 26th wedding anniversary, so that worked out quite nicely.

Answer 4

she oversees the project that I have been part of

Well that is a problem. Imagine the role reversed. You are the middle-aged male manager and she is one of the new young female recruits. Do you think you would get away with flirting among all the young girls and being hands-on?

There are some problems here. Clearly, this is favoritism and sexist- though your company clearly gives a free pass to women who do this behavior so shame on them. History has shown that successful companies are led by competent management. A competent manager strives to respect everyone, is respected in-turn by everyone, helps increase productivity, identifies problems and provides solutions, leads by example, looks out for the well-being of all their subordinates, and is fair. A competent manager does not show favoritism and does not date subordinates. Nor should subordinates receive 'signals' from managers.

Bear in mind if you date this person you are connected by association professionally and personally. You could become "that guy", where you are judged solely on that relationship and your entire work ignored. Your promotion could either become more difficult, or if you get promoted- it appears as favoritism ("she promoted her boyfriend").

The managerial relationship aside- successful relationships tend to require a little bit of separation. You need breathing room and time alone to be a productive person. This is almost impossible if working in the office next-door and seeing this person daily. There are a lot of nice, flirty women out there, in and outside of the office. You don't have to date this person, and dating a coworker is often advised against (just do any internet search on this topic).

Remember your job is important and you receive a salary in compensation for fulfilling your contractual duty. Dating a flirty manager is not part of that duty. Trying to date her appears unprofessional and only makes your job harder as you try to juggle both professional and personal relationships.

How to tell a coworker that you would like to date them?

Tell them you would consider it in a normal circumstance, but since they are your coworker/manager the relationship should remain professional.

Answer 5

I think Edwin Buck's answer is very good, but it's possible it could be overly pessimistic about your chances if you "play such a game". It's also possible they're overly optimistic about your chances if you choose to abstain.

The vast majority of these relationships that I've heard about went the way Edwin said, so I'd recommend doing the suggested homework: find out what happened to other men she showed interest to like this. But also find out as much as you can what those men were like, because how similar you are to them could indicate how similar this will go for you if you take her up on her interest - or fail to.

Your fourth point on what she's done suggests that there probably won't be a long term option, unless her lack of focus on one target is due to biological clock desperation. Don't think that she's showing attention elsewhere just to get your attention. Some women do that, but most of them are in high school or college. Those that persist in that sort of behavior tend to be drama queens, because seeking jealousy is a good way to ask for drama.

My next suggestion is to prepare yourself for the worst: start saving as much money as is feasible, keep your resume updated, prepare yourself as much as you can psychologically for things going poorly, because you may not have any additional warning indicators. Even if all of her exes were promoted as consolation awards for the loss of her affections, you could still be treated differently and fired.

Even if you opt to not pursue her, you could wind up fired. If she's able to get a C-level to play matchmaker for her, she probably doesn't feel like she's taking any career risks whatever she does with you. Normally, moving where you sit would be a job for your boss or your manager. Unless the company is so small that either you are reporting to a C-level as a newcomer or your boss is, having a C-level do it is a power-play.

That having been said, it's also possible that this is a golden opportunity. The most likely good experience from this would be career advancement and some good learning experiences.

You could also wind up like my prior boss (he retired), who met his wife like this. She had been looking for a smart, non-submissive supporter of women's rights who didn't want kids that she could get along with, and he happened to be the first one she found. I'm not suggesting Mary is like that - Mary is her own person, and as I don't know anyone IRL who's in her 30s and in Asia, I guarantee I don't know her. But it's possible she has a type she's trying and failing to find.

Even if her interest indicates that you aren't going to be with your current employer much longer, you may still be able to leverage the situation to pick up some skills or details for your resume that will help you secure a better next job.

TL;DR: you live in interesting times, good luck. I recommend being the best person you can be, because I have personally found that a good reputation tends to work about as well as anything to protect from things going wrong. But the results of your research about who she's been interested in before will probably be a better guide than anything specific I can say.