Coworkers: To Date or Not to Date?

[Batty Belfry]

There is a coworker I like who has become comfortable with me over the half of a year I have seen her. When she trained me for the first time, I saw that she would turn to stare at me, before quickly turning back to the tutorial on the computer. She started approaching me after I complimented her on her outfit one day. She would call me early mornings and late nights about working open shifts, play with her jewelry when talking to me, change her hair and clothes. She even wore all grey to match my all-grey attire during the winter months. One night she stopped me and made an excuse to talk to me about the calendar when really she just wanted me to talk about her matching grey clothes. She and another female coworker would talk about me too.

I took things slow to observe these signs and have not given any other compliments since. I have noticed that on certain days she would be absent during my shifts whenever I would tell her "good night" and "see you soon." For example, I sent a small box of cookies to her and the supervisors the day after Valentine's Day (she was absent on Valentine's Day), but I don't know if they ever received them, and if they did, no one knew who to thank for them.

Despite that small move to pursue her, the signs seem good, if not fortuitous. However, the supervisors she works with leave an impression on her. She has a good, intelligent, and honest nature about her, but I feel like she gets lost at times in the brainwashing veil of "work mode." I understand we are here to do our jobs, I just don't know if the signs were actually mixed signals. Sometimes I think she is only being nice because the supervisors know that she responds to me just as I respond to her. The ploy here would be to turn me into a "yes man." Other times I feel like she genuinely respects me and we share this intense energy when we are near and alone, whether we are with or without words.

I have two plans of action in mind below, but please let me know if I'm in over my head. Your advice and experience is duly appreciated.

Plan 1
I would leave a letter inviting her to coffee in her mailbox at work. A discreet way that does not embarrass, pressure, or raise the attention of others. It would be for her eyes and at her discretion only. If she brings it up, she brings it up, but if she doesn't, she doesn't.

Plan 2
I ask her out for coffee when she and I have a moment to ourselves at work. A direct approach would show confidence and attraction that I originally showed her. I have no issue talking to her and she reciprocates interest from what I've seen and heard from her.

Risks

• The office is small and voices are an earshot away.
• She reports it to the supervisors.
• The supervisors confiscate it and let me go for not being transparent.
• Pursuing her might make her feel shy, dismissive, offended, vindictive, etc.
• An office romance may lead to workplace favoritism or gossip.

I have not dated since college, which was six years ago. We are both English majors and we graduated from the same college too. I can't get to know her well in the office. I like what I see but I need to know if I will like who she'll be. I need to know how much I like her.

Should I date my coworker? Should I pursue her, pursue her differently, or not at all?

 

[onceaking]

Plan 1
I would leave a letter inviting her to coffee in her mailbox at work. A discreet way that does not embarrass, pressure, or raise the attention of others. It would be for her eyes and at her discretion only. If she brings it up, she brings it up, but if she doesn't, she doesn't.

Plan 2
I ask her out for coffee when she and I have a moment to ourselves at work. A direct approach would show confidence and attraction that I originally showed her. I have no issue talking to her and she reciprocates interest from what I've seen and heard from her.

Plan 3
Find another job and once you get a new job ask her out. That will stop this potential relationship from affecting your career.

Risks

• The office is small and voices are an earshot away.
• She reports it to the supervisors.
• The supervisors confiscate it and let me go for not being transparent.
• Pursuing her might make her feel shy, dismissive, offended, vindictive, etc.
• An office romance may lead to workplace favoritism or gossip.

Another two risks:

You bring all the tension from your relationship into work and have ridiculous fights with each other in the office (I've worked with couples and have seen this happen).
You end up breaking up with her and she goes about trying to get you fired.

If I were you I would either find another job and then pursue a relationship with her or remain at the company and forget all about her. There's too much risk with an office romance. You could end up ruining your career or at the very least lose your job.

 

[Batty Belfry]

Plan 3
Find another job and once you get a new job ask her out. That will stop this potential relationship from affecting your career.



Another two risks:

You bring all the tension from your relationship into work and have ridiculous fights with each other in the office (I've worked with couples and have seen this happen).
You end up breaking up with her and she goes about trying to get you fired.

If I were you I would either find another job and then pursue a relationship with her or remain at the company and forget all about her. There's too much risk with an office romance. You could end up ruining your career or at the very least lose your job.

I understand you. The job is not a full-time career, just a part-time job. I do not see her regularly, she and I have our own schedules. But she has aligned our schedules more than once.

I also already work other part-time jobs that I could make full-time, but that is beside the point. She does not come off as someone who is immature, despite her wanting me to comment on her outfit again. I think she, and I, are mature enough to keep work and relationship separate from each other.

That is why I think taking her out on a date would allow me to know this for certain and her better outside the workplace.

 

[onceaking]

I also already work other part-time jobs that I could make full-time

Since that's the case then I would go for it then. But I would leave the office where she works though.

 

[Batty Belfry]

Since that's the case then I would go for it then. But I would leave the office where she works though.

That's the difficult choice. For men, they have a financial clock while women have a biological clock. Where I work with her now, the schedule has been more consistent than my other part-time jobs. I will have to weigh my options closely.

I have waited patiently and have not been clingy or desperate. I want to see her be more direct with what she wants, but I realize women tend to be more implicit in their delivery, for example, through body language.

 

[Mob Barley]

After several months of knowing her it's definitely safe to ask her out. All this fear of being reported to HR, in the worst case scenario, most likely will not happen. If it does you can easily explain the situation with all the text you two have exchanged.

There was a coworker who I was instantly attracted to. I trained her on the job, we did several shifts together and I asked her out like 3 different times within the past month. First time she said yes but the time she was available didnt work for me. Second time, she says yes but walks that back saying she's tired. Third time she's like going around the question. The 3rd time I was kinda hurt and I let her know this. After several hours of no response I said " I guess I should fuck off then lol", knowing she's literally always on her phone. It seems like she left for a new job now.

The sexual tension between us felt great but I think I got overly emotional. She called me on the phone crying about some other guy while on a skateboard and that felt like she really wanted me to be apart of her life. Also told me she'd be down to take an international trip with me this year so it felt like a major green light, all gas no brakes. Small part of me wants to reach out again just to see how she's doing

 

[Batty Belfry]

After several months of knowing her it's definitely safe to ask her out. All this fear of being reported to HR, in the worst case scenario, most likely will not happen. If it does you can easily explain the situation with all the text you two have exchanged.

There was a coworker who I was instantly attracted to. I trained her on the job, we did several shifts together and I asked her out like 3 different times within the past month. First time she said yes but the time she was available didnt work for me. Second time, she says yes but walks that back saying she's tired. Third time she's like going around the question. The 3rd time I was kinda hurt and I let her know this. After several hours of no response I said " I guess I should fuck off then lol", knowing she's literally always on her phone. It seems like she left for a new job now.

The sexual tension between us felt great but I think I got overly emotional. She called me on the phone crying about some other guy while on a skateboard and that felt like she really wanted me to be apart of her life. Also told me she'd be down to take an international trip with me this year so it felt like a major green light, all gas no brakes. Small part of me wants to reach out again just to see how she's doing

Today, she and I were the last ones to leave the building. In that moment, I could have asked her out for coffee sometime, but instead I waited to see if she would say anything else. She just repeated what she sent in an email to me about next week's schedule and working over spring break. Could she have been nervous? Sure. Has she been distant through her use of professional speech that feels scripted? It feels that way.

I am tempted to see what she says and how she reacts to a date, seeing how she is giving the elephant in the room a cold shoulder. A direct approach I think is the best way; at least I will get an answer in person.

 

[Batty Belfry]

I talked with her about updating my availability to work another day in the week before I asked her out for coffee and she said "it would be inappropriate."

I know she didn't say yes, and I know she didn't say no, but I am not convinced she completely rejected me. I also am not going to force to convince myself she still likes me or is still interested. There is definitely a work veil she is protecting and, I think, using to hide certain feelings.

It would be silly, even neglectful (to some), to quit my job to date someone. I don't think quitting is the right move here by the way. I don't plan on finding ways to change her mind. I made my move, was cordial about it, and moved on.

It is unfortunate, for her, for me somewhat, but I asked and I was comfortable doing it.

 

[Mob Barley]

I talked with her about updating my availability to work another day in the week before I asked her out for coffee and she said "it would be inappropriate."

I know she didn't say yes, and I know she didn't say no, but I am not convinced she completely rejected me. I also am not going to force to convince myself she still likes me or is still interested. There is definitely a work veil she is protecting and, I think, using to hide certain feelings.

It would be silly, even neglectful (to some), to quit my job to date someone. I don't think quitting is the right move here by the way. I don't plan on finding ways to change her mind. I made my move, was cordial about it, and moved on.

It is unfortunate, for her, for me somewhat, but I asked and I was comfortable doing it.

Telling her that you'd rearrange your schedule for her, before a 1st date, does seem too thirsty. At least you got to ask and see how she responded. Definitely worth the shot. Quitting definitely isn't the right move haha! Keep it cordial with her and try to find someone else.

 

[onceaking]

I talked with her about updating my availability to work another day in the week before I asked her out for coffee and she said "it would be inappropriate."

I agree with her. If I was really into a co-worker I would try to find another job but I know that's quite extreme and I'm looking for a new job so I know it's not easy to just get one. Anyway, you've asked her so it doesn't really matter now.

 

[Batty Belfry]

@Mob Barley I didn't change my schedule to date her, I did it to add another stream of income. You are right, if I were to change my schedule for her, it would be thirsty.

@onceaking When she told me it would be inappropriate, I didn't argue. I told her, "I get it," and she replied, "Thank you." No complications at work. She either is not wanting a relationship, already has one, or is more distracted/interested in the job. It is confusing considering her aims to impress me with her attire, her proximity to me during my shift, talking to me about work when ever she gets the chance, etc. But again, I cannot read minds or get a confession. It is up to her whether or not she has something to say now. Good luck with landing your new job!

I also disagree with the "dating a coworker is taboo" camp. I think coworkers can date each other if it is mutual, measured, and unrelated to work. I don't hold it against her for not wanting to date a coworker either.

Better to choose the woman who chooses you.

 

[Ngo27]

It was nice to read about your potential dating at work situation. Being in a similar situation, I'm feeling something more for a coworker who became single few months ago. She may already have me in friendzone since we worked together for a few years. I am not sure about pursuing the relationship since I am working on changing career currently. There's also the lack of dating experience on my part. Please share your advice and thoughts.

 

[Batty Belfry]

It was nice to read about your potential dating at work situation. Being in a similar situation, I'm feeling something more for a coworker who became single few months ago. She may already have me in friendzone since we worked together for a few years. I am not sure about pursuing the relationship since I am working on changing career currently. There's also the lack of dating experience on my part. Please share your advice and thoughts.

@Ngo27 I'm glad you could relate to my situation.

I have not dated since college. I was inexperienced and naïve back then, but with experience comes awareness. I was rusty getting back into courting and dating, but what restored me was a slow approach.

Before I asked her out, I was working with her for over a few months. During that time, I was building attraction and connection with her. Conversations revolved around work mostly, she never shared anything personal, but we got comfortable working alongside each other. She trained me for the job and I was listening, but not engaging, in small talk so much. I noticed she looked at me and slowly turned back to continue my training. What made her more interested in me was when I said she looked good in her outfit. I said this the day before holiday break, which gave her time to think about that moment. The day I got back to work, she was not there; a supervisor said she was on lunch break. The following day, she shows and I do not talk to her as I clock in, but she walked up to me, stood squarely in front of me, and said hello with a deep smile and look in her eyes. After that, she started to change her outfits more, her hair, and even started matching the colors I wore.

The moral here is to give a genuine compliment genuinely. Do not say it if you do not mean it. Also, do not shower her in compliments either. Take your time and observe how she interacts with you and others.

For her, she understood how important work was. For example, I was running late to work one day, so she had to cover for me until I got there. I professed that I was working another job and got stuck in traffic. I apologized and she forgave me. When we were talking, she was standing much closer to me too, playing with her necklace.

I knew she was interested in me, but I was doubting whether to pursue her too. She would not open up as much as I did, and I suspect it had to do with keeping her mind on her work, but had I not asked her out, I would not have gotten an answer.

Also, people say no for many reasons, but do not dwell on the "no" or the "why." Do not wait for someone who does not choose you. Do not wait for someone to change their answer. People can change over time, a "no" can become a "yes," with the right understanding, actions, and needs. Otherwise, expecting or waiting for someone to date you is like expecting or waiting for a dog to meow.

My dad always told me, "If you don't ask, you don't get." But again, give each other breathing room, learn about each other through innocent, personal questions. Turn those answers or quirks into teasing to build attraction and connection. After enough time has passed between yourselves and you have gotten to know each other better while at work, decide if a date and a romantic relationship is something you want to have, then ask her.

I also asked during a busy day, saying, "I know you're busy, but I'd like to take you out for coffee." Just like that; I could have added, "I'd like to get to know you better," but brevity is better in these situations. See how she reacts, but be cordial about it. Don't force the issue or negotiate, be flexible and move forward with mutual respect and understanding.

Every situation comes with its own varying conditions, so take my advice only if you think it applies or would help your situation. Feel free to contact me here or through direct message.

- P.S.
A career change does not hurt your chances with her either. No conflicts since you would both work for different companies. After getting to know each other better at work, you could casually bring up your wanting to change careers to her to see how she reacts. But the career change has to be for you. Do not change careers just to date her or if she is not interested. If she is still interested before and after you have changed careers, think over pursuing her and stay in touch. Then you could see about asking her out.

 

[Coub]

What's improper of asking out a coworker? I think I live in a different culture... This is just a coffee and if you don't want to get closer it doesn't mean you won't be able to cowork effectively anylonger. We're just humans. My parents and many other people met in their workplaces. Unless you're not able to distinguish work time and free time then there's nothing wrong and you did the right thing. It's always better to give it a chance if you feel like it than regreting it for rest of your life.
What about students dating their teachers? In university for example. Do you think it's inappropriate too? Student is teacher's client!
If both sides feel like giving it a go then live the moment.

 

[Armin1]

Hello buddy
I think women don't wait forever for you to make a move. She did her job and you noticed she's interested in you. Next is your turn and if you don't use it, makes her a little uncomfortable because she would think that she's not enough and that feeling of interest converts to hate (for a while, of course, then every thing will get good but she's unavailable for you forever) or she might think you're not brave enough. So I f you like her too, make a move before it's too late)

 

[Batty Belfry]

@Coub The intentions were good, but I respect her for not wanting to mix work and a relationship. She does prioritize work over relationships from my time observing her.
@Armin1 I definitely see that female perspective. I don't want to play the "what if?" game now, but I realize acting on those signs earlier could have made a difference. I was taking it slow because I did not want to rush any of our decisions or jeopardize our professional ties. I also only complimented her once, which was a brave move in the first place. I did not have her reciprocate interest beyond her looks or work ethic, but that could be her acting on her ego and privacy. I did ask her out however, and could she have changed her mind about me during my slow approach? Sure, but I don't dwell on that and my expectation is not to change her mind moving forward. I just want a relationship that is reciprocal. I respect her and respect myself.

 

[Armin1]

Very good attitude. I like professional people like you. I would say stop thinking and give it a try. A normal day go ask her out, and speak about your feelings. Say what exactly had told us, That you like her, and you did dewelld because you didn't want to mix career stuff and so on.
What is the worst thing that would happen? She says "no, thank you, I already have plans" which is good for you too, because she gets out of your mind.
But what if she says yes, and every thing goes well and she was "The ONE" for you, and you're relationship was so so good and enjoyable?
So it worth trying.
(Sorry for my poor English. I know it's on your nerve)

 

[Batty Belfry]

Very good attitude. I like professional people like you. I would say stop thinking and give it a try. A normal day go ask her out, and speak about your feelings. Say what exactly had told us, That you like her, and you did dewelld because you didn't want to mix career stuff and so on.
What is the worst thing that would happen? She says "no, thank you, I already have plans" which is good for you too, because she gets out of your mind.
But what if she says yes, and every thing goes well and she was "The ONE" for you, and you're relationship was so so good and enjoyable?
So it worth trying.
(Sorry for my poor English. I know it's on your nerve)

@Armin1 Thank you for the kind words. Your English does not bother me, it is very good.

You are saying I should ask her out again sometime, but share my feelings and intentions not to mix career and relationship with her when I ask? I should reciprocate exactly this, what she said to me, back to her?

I did only ask her out once, but when she said it would be inappropriate, I took it as a soft no, but a no nonetheless. She could have not been ready for a relationship, she could already be in a relationship, or she could be recently single. All these things I cannot know without her opening up to me. Since I have opened up to her and showed my interest by asking her out once, asking her out again may or may not be advisable.

Letting her be, giving her time to herself, gives us room to see how we interact and behave again and moving forward.

I might act on her signs sooner, if they show again, and I might ask her out again, if she shows more interest or opens up to me more. I still like her, I've just been given mixed emotions about the situation. I will not let my emotions control how I do my job or how I treat her though.

 

[Ngo27]

@Batty Belfry I like taking a slow approach and it's time I ask. During the time we worked together, we've talked about various things such as movies and fitness. I waited a few months for myself to ponder about my intentions on dating and for her to settle after becoming single. Recently, I asked her to watch a movie together since I have a coupon.
I feel it's time I enter the dating scene especially after these 2 years of pandemic. Starting with someone that I've established rapport makes it more comfortable than browsing on dating apps.

 

[Batty Belfry]

@Batty Belfry I like taking a slow approach and it's time I ask. During the time we worked together, we've talked about various things such as movies and fitness. I waited a few months for myself to ponder about my intentions on dating and for her to settle after becoming single. Recently, I asked her to watch a movie together since I have a coupon.
I feel it's time I enter the dating scene especially after these 2 years of pandemic. Starting with someone that I've established rapport makes it more comfortable than browsing on dating apps.

Glad to hear you making progress @Ngo27 You have to look into someone's eyes and feel something good. You cannot do that over an app. The point of the first date is to see if you both enjoy each other's company. See what is in her heart and in her head, and the same goes for you. Reciprocate, respect, review. Let us know how you get along.