What is a clever/low pressure/indirect way to ask out a co-worker [UPDATED]

[Mac0908]

40M here. Been getting to know a co-worker of mine for a good few months now and we've built some nice momentum talking more and more. I know she enjoys talking to me as I make her laugh quite a bit and she has come to me on a few occasions for conversation as well which I felt has been a good sign as most female co-workers are very brief and keep distance from single men in the office. Sometimes our conversations have gone on for well over a half an hour so these are definitely not quick 4-5 minute generic work chit chats. But while there is very good general chemistry between us, for the life of me I still can't tell if I'm just a co-worker she enjoys talking to in order to pass some time, or if she may have some slight romantic interest. In more recent memory I've thrown some subtle flirting into our chats but she never seems to pick up on it  or just doesn't choose to flirt back. For example I joked about how I may be getting a new position one day soon and then she would "Never see me again". She simply laughed and smiled. I should note that we do NOT work in the same area together everyday which is a good thing. More like once every two weeks. So if she happened to say no it wouldn't be that weird.

For more context, she is 29 years old which while not crazy, is significantly younger than me. I wouldn't care of course, but I have a hunch she might. We have never even exchanged phone numbers (no need to) and the only time I ever referenced hanging outside of work was when I nonchalantly and semi-sarcastically mentioned how we will celebrate with a drink when she gets her promotion to which again, she laughed and smiled, quickly said ok, before we quickly moved onto another topic. We have also never gotten lunch or coffee during work. I considered asking her to walk with me to get lunch one day, but that would likely be a mistake as other co-workers would see us leaving together which I wouldn't want and I'm almost certain she wouldn't be crazy about either. It would just feel weird. So that's out of the question.

So, I've come to the conclusion that I should just simply ask her out. She likely isn't getting a promotion anytime soon and I don't feel like waiting for such a thing. That said, this is still work and this woman is not exactly making this easy for me lol. So does anyone have any very clever ways to ask out a woman or hint at making plans, etc, so it comes off super casual and indirect? And lastly, what would a good realistic get together look like? Its even more difficult bc she lives rather far from me (solid hour) so its not like I could say I want to check out a place near me and she should come. It would have to be some specific place we picked thats sort of in the middle of us. In addition, she also works super late (much later than me), so even going out after work somewhere is out of the question ((ugh)). I have been thinking a good idea may be to GAUGE her reaction about getting together first, in the sense of saying something along the lines of "So when are we going out for (insert activity or drinks)??". But, I feel that could backfire as it could put pressure on her as in she'd feel like I'm assuming she's already ok with going out with me. I guess the vibe would really have to be perfect.

Thanks in advance.

Edited yesterday at 08:56 PM by a LoveShack.org Moderator

[Gaeta]

So, you want to invite her out on a date but without her knowing it's a date lol

Start with inviting her out to lunch. You don't need to walk there together, just tell her to meet you at XYZ at such time. 

How is that going to work if you want to date her but don't want people around to know about it. 

Reading through the lines I don't think she is interested in you further than an office friendship. Men often think because we chitchat and laugh at their jokes it means we're romantically interested in them. I got in trouble a few times just for being friendly like this. 

[Sony12]

Yeah generally when people are interested in a coworker romantically and want to go through with it they make it very obvious. Just friendly chat at work is often just that-friendly chat at work. 

Edited November 28, 2024 by Sony12

[Mac0908]

54 minutes ago, Gaeta said:

 

Reading through the lines I don't think she is interested in you further than an office friendship. Men often think because we chitchat and laugh at their jokes it means we're romantically interested in them. I got in trouble a few times just for being friendly like this. 

 

34 minutes ago, Sony12 said:

generally when people are interested in a coworker romantically and want to go through with it they make it very obvious. Just friendly chat at work is often just that-friendly chat at work. 

True. I don't know if she is interested in me in anything more than office friendship. So you both could be absolutely right. Maybe there is no romantic interest at all. But, what I do know at 40 years old and 19 years of being in multiple professional environments is I have never had "chit chats" like this. Very lengthy, consistent conversations everytime we see each other revolving around everything from work to hobbies to family, etc. The only thing we've never spoken about is our dating lives. Though I do know she's single, of course.

Like I had alluded to in my post, one thing I've noticed for certain is 99% of the time, usually there is always this underlying thing at work where more attractive, (and mentally stable at least), women seem to keep their distance from men, myself included, whether they are single or not. Its mostly because they do not want to give men the wrong idea even in the slightest. Meanwhile this woman has gone out of her way to come to me and chat on a few occasions. Again, I know this could go nowhere, I'm just making some points. I should have noted though, that she does seem a little "odd" and different in the sense that she is the overly friendly type in general, still lives at home with parents, and I just get a bit of a sheltered vibe from her. To be honest I wouldn't be surprised if she were never in a long term relationship. That sort of thing. Just seems a tad inexperienced in life is the vibe I've gotten. I cannot say if she speaks to any other single men like she does me, because she works mostly with women and married men.

Edited November 28, 2024 by Mac0908

[Gaeta]

As an experienced 40 yo man, why would you be interested in a 29 year old woman still living at her parents? She's younger but she's not a kid anymore and she never felt the need to spread her wings beyond her parent's basement? 

[Mac0908]

2 minutes ago, Gaeta said:

As an experienced 40 yo man, why would you be interested in a 29 year old woman still living at her parents? She's younger but she's not a kid anymore and she never felt the need to spread her wings beyond her parent's basement? 

Damn, quite the typical overly harsh and critical online forum poster aren't you? Parents basement? Not quite. And if you must know, given the catastrophic state of housing prices go, particularly in the area we live in (big city area), kids moving out is becoming more and more difficult. 2 grand a month for a nice 1 bedroom anyone? Yes, that's accurate. She's also not making an extraordinary amount of money. But I digress now.

But to be real with you about something you are trying to say, I'd be lying if the one thing that's a bit of a turn off for me is just how much "older" I feel sometimes when talking to her. I don't mean this in a sense of me looking older as I do think I have a youngish face, but more just learning about her and realizing just how much more experienced I am in certain areas. That all being said, it doesn't take away from our great chemistry we seem to have when conversing and getting to know each other. I would never NOT go on a date with someone like her just because she's never lived on her own. Is it ideal? No. But its not a dealbreaker...

[Sony12]

28 minutes ago, Mac0908 said:

 

True. I don't know if she is interested in me in anything more than office friendship. So you both could be absolutely right. Maybe there is no romantic interest at all. But, what I do know at 40 years old and 19 years of being in multiple professional environments is I have never had "chit chats" like this. Very lengthy, consistent conversations everytime we see each other revolving around everything from work to hobbies to family, etc. The only thing we've never spoken about is our dating lives. Though I do know she's single, of course.

Like I had alluded to in my post, one thing I've noticed for certain is 99% of the time, usually there is always this underlying thing at work where more attractive, (and mentally stable at least), women seem to keep their distance from men, myself included, whether they are single or not. Its mostly because they do not want to give men the wrong idea even in the slightest. Meanwhile this woman has gone out of her way to come to me and chat on a few occasions. Again, I know this could go nowhere, I'm just making some points. I should have noted though, that she does seem a little "odd" and different in the sense that she is the overly friendly type in general, still lives at home with parents, and I just get a bit of a sheltered vibe from her. To be honest I wouldn't be surprised if she were never in a long term relationship. That sort of thing. Just seems a tad inexperienced in life is the vibe I've gotten. I cannot say if she speaks to any other single men like she does me, because she works mostly with women and married men.

Making friendships at work is more important to some than it is to others. For some it is a way to help them get through the workday. However it usually doesn't mean that they are interested in being around you outside of that office environment. Usually when they are interested in selling you outside of the office environment they will say as much.

[Gaeta]

8 minutes ago, Mac0908 said:

Damn, quite the typical overly harsh and critical online forum poster aren't you? Parents basement?

Those are questions that need to be asked no? 

Yes you are more experienced and maybe some of it because of your 11 years older but also because you have a life experience normal for a 40 yo man and she is behind on the life experience a woman of 29 should have. 

All that being said, I am not telling you to not date her, I am pointing details here and there you should pay attention to. 

On a side note: People often bring up the economical situation for staying with their parents till 30+. This is just an excuse. Most early 20sh want their independence, they go live with room-mates, they learn how to fetch for themselves, how to make economical sacrifice to get by monthly, they find better paying jobs and they slowly better their situation. All this struggle is GOOD. It makes them resilient, resourceful, independent. 

To get back to your question. You like her, ask her out. There is no way around it. If she says yes then wonderful! If she says no then nothing lost and you know where you stand. 

 

[Mac0908]

Update to an older thread about a co-worker I've gotten to know for a good few months. Though we only spoke to each other once every 1-2, sometimes even 3 weeks, we progressed to a very nice little work relationship, having great conversations and laughs everytime. I never really got to the point though where I felt she was definitely interested and considering we work for the same company, I wanted to at least see some interest before I'd make the move to ask her out. That said, one night at work she went out of her way to come all the way back to my office which was unprecedented for her consindering all of our convos were either at her desk or common areas. She had on several occasions approached me in common areas. But back in my office, it was a quick convo, but I viewed it as a great sign. Ironically, about two weeks later, she got a small promotion at work. Before the interview two weeks ago I had wished her luck via text. She said thank you and liked my text. I found out she got the job in the morning just yesterday. Last night, she actually texts me saying "Hey, I got the job btw". I took this as my opportunity...

I wrote "Congrats!! It finally happened. We should grab a drink at some point in the next week to celebrate  "

Her response was over two hours later, saying "Thanks. I'm so happy I don't have to do (her specific job duty) anymore   "

No acknowledgment of my comment about drinks. No thanks but I'll pass. No white lie. No NOTHING.

To be honest, even though she's quite a bit socially awkward of a woman, I was shocked, not to mention pissed, and kind of hurt. After many months of treating her so well at work, her being sweet as hell to me, us having great fun conversations about everything, this was what I was left with.

Any thoughts to make me understand what may have happened would be appreciated...

[basil67]

58 minutes ago, Mac0908 said:

I was shocked, not to mention pissed, and kind of hurt. After many months of treating her so well at work, her being sweet as hell to me, us having great fun conversations about everything, this was what I was left with.

I'm sorry it didn't work out, but dude, you're sounding really incel here!   Treating coworkers well should be default.  It's Respect 101.   Surely you don't treat the rest of your coworkers badly?   Being able to have fun conversations and her being sweet is a work friendship, and I daresay she's friendly to all. Let's be clear,  women do not owe you dates because you treat them well.

You do have a right to be disappointed that she doesn't want to date you,  but you have zero grounds to be pissed or hurt that she only sees you as a friendly coworker in a workplace.  And given she is simply a coworker, it's OK that she chose to dodge responding to your invitation for drinks.  One should never feel obliged to have awkward personal conversations with another coworker. 

This whole awkwardness is why so many people advise against dating in the workplace.

Edited yesterday at 09:14 PM by basil67

[Mac0908]

20 minutes ago, basil67 said:

I'm sorry it didn't work out, but dude, you're sounding really incel here!   Treating coworkers well should be default.  It's Respect 101.   Surely you don't treat the rest of your coworkers badly?   Being able to have fun conversations and her being sweet is a work friendship, and I daresay she's friendly to all. Let's be clear,  women do not owe you dates because you treat them well.

You do have a right to be disappointed that she doesn't want to date you,  but you have zero grounds to be pissed or hurt that she only sees you as a friendly coworker in a workplace.  And given she is simply a coworker, it's OK that she chose to dodge your invitation for drinks.  One should never feel obliged to have awkward personal conversations with another coworker. 

This whole awkwardness is why so many people advise against dating in the workplace.

The only thing I was disappointed, pissed and upset about was that she didn't acknowledge my invite for drinks. I guess I should have made that more clear. I 100% would have been fine if she politely/respectfully declined, but instead I was essentially ignored. I'm sorry but after developing somewhat of a significant work relationship with her for a substantial amount of time, I can't get behind how she handled my invite.

It may have been "OK" for her to dodge the invite if I lets say just met her a week and a half ago, but I met the woman a year and a half ago and got to know her relatively well over the last 5-6 months in particular. I'm just being honest in that it felt very cold and now I almost feel as if there would be some underlying awkwardness between us if we ever see each other in the future as opposed to if she just acted mature and gave me a white lie or polite rejection.

Edited yesterday at 09:33 PM by Mac0908

[basil67]

But this is a workplace, not a social situation.  She shouldn't be put in the position of having to deal with unwelcome invitations for dates in the first place.

[Mac0908]

11 minutes ago, basil67 said:

She shouldn't be put in the position of having to deal with unwelcome invitations for dates in the first place.

"Unwelcome"? That's subjective. I became somewhat close with this woman over the course of the last 5-6 months. No offense at all, but you weren't there. I was.

She's the one coming out of her way completely to my office (entirely different area of the building) to chat. She's the one texting *me* telling me she got the promotion at first, unprompted. She knew it was something we had talked about for a while and thought of me. Yes, in retrospect that was just her being work friendly, but I also feel like if she were more intuitive she would have put the brakes on any conversations with me seeing as how I really stepped things up in the last few months.

Edited yesterday at 09:47 PM by Mac0908

[Sony12]

1 hour ago, Mac0908 said:

"Unwelcome"? That's subjective. I became somewhat close with this woman over the course of the last 5-6 months. No offense at all, but you weren't there. I was.

She's the one coming out of her way completely to my office (entirely different area of the building) to chat. She's the one texting *me* telling me she got the promotion at first, unprompted. She knew it was something we had talked about for a while and thought of me. Yes, in retrospect that was just her being work friendly, but I also feel like if she were more intuitive she would have put the brakes on any conversations with me seeing as how I really stepped things up in the last few months.

I think you need to begin trying to figure out the differences between just being friendly and nice and being interested.

Being friendly with coworkers helps some people get through the workday better. But it doesn't mean they want to turn it into anything more than that.

I highly recommend you just let her be and if she tries to talk to you again be cordial with her. You haven't done anything wrong yet but if you begin harassing her you will find yourself in HR.

 

 

 

[basil67]

2 hours ago, Mac0908 said:

"Unwelcome"? That's subjective. I became somewhat close with this woman over the course of the last 5-6 months. No offense at all, but you weren't there. I was.

She's the one coming out of her way completely to my office (entirely different area of the building) to chat. She's the one texting *me* telling me she got the promotion at first, unprompted. She knew it was something we had talked about for a while and thought of me. Yes, in retrospect that was just her being work friendly, but I also feel like if she were more intuitive she would have put the brakes on any conversations with me seeing as how I really stepped things up in the last few months.

She deliberately ignored your invitation to drinks.  What part of her reaction makes you think your offer was welcome?

With you stepping things up, did you do something obvious like send flowers or give her gifts?  If so, then yes, she should have told you she wasn't interested

 

[Mac0908]

1 minute ago, basil67 said:

She deliberately ignored your invitation to drinks.  What part of her reaction makes you think your offer was welcome?

Agree to disagree. This really isn't about whether or not she felt it was welcome or unwelcome or not. It's about how any decent person wouldn't ignore an invitation for drinks from someone they've known well for a lengthy period of time. Again, I wasn't Joe Schmo who only met her one week ago. Did she obviously view it as unwelcome? Yes, I won't deny that. But most people I'm sure would agree that how she handled it was immature. 

[Sony12]

1 hour ago, Mac0908 said:

Agree to disagree. This really isn't about whether or not she felt it was welcome or unwelcome or not. It's about how any decent person wouldn't ignore an invitation for drinks from someone they've known well for a lengthy period of time. Again, I wasn't Joe Schmo who only met her one week ago. Did she obviously view it as unwelcome? Yes, I won't deny that. But most people I'm sure would agree that how she handled it was immature. 

Have you even been around her outside of the office that much at all? If not then how can you claim that you knew her all that well? In general most people put a face on when they are at the office place. It seldom is who they really are.

I for instance work with a group of people. We talk and joke around with one another all the time and in general make a good workplace team. However once we step out of those doors we completely go our own ways and have nothing really to do with each other. And I honestly think to myself how annoying they are and that I'm glad I am only having to be around them when I am getting paid for it.

Edited 21 hours ago by Sony12

[Mac0908]

35 minutes ago, Sony12 said:

Have you even been around her outside of the office that much at all? If not then how can you claim that you knew her all that well? In general most people put a face on when they are at the office place. It seldom is who they really are.

I for instance work with a group of people. We talk and joke around with one another all the time and in general make a good workplace team. However once we step out of those doors we completely go our own ways and have nothing really to do with each other. And I honestly think to myself how annoying they are and that I'm glad I am only having to be around them when I am getting paid for it.

No we never hung out outside of the office but we also never had opportunities to do so as she worked completely different hours than me, and on top of that, its not an office that does things together outside of work. There was a Christmas party, but she had other plans that night unfortunately. I'm not saying we were the best of friends, acted like a married couple of anything of that such. But in the grand scheme of co-workers we developed a relationship that absolutely had some substance. There were several occasions we spoke for  nearly 45 minutes, there were times when we spoke about some deep subjects involving family and friends, what our life goals are, etc. Not just random chit chat involving work talk and sharing funny meme's from Instagram.

[Sony12]

30 minutes ago, Mac0908 said:

No we never hung out outside of the office but we also never had opportunities to do so as she worked completely different hours than me, and on top of that, its not an office that does things together outside of work. There was a Christmas party, but she had other plans that night unfortunately. I'm not saying we were the best of friends, acted like a married couple of anything of that such. But in the grand scheme of co-workers we developed a relationship that absolutely had some substance. There were several occasions we spoke for  nearly 45 minutes, there were times when we spoke about some deep subjects involving family and friends, what our life goals are, etc. Not just random chit chat involving work talk and sharing funny meme's from Instagram.

Well there you have it. You have never been around one another outside of work or work related activities. So don't act like you ever really knew her all that well. I know a lot about my coworkers personal lives as well but it doesn't mean I have much interest at all in being a part of their life outside of the office.

She likely just enjoys being social during work because it helps her get through the day. She never as far as you mentioned so far made any reference to her wanting you two to spend time together outside of the office. She was never leading you on. You just mistook her friendliness for being something more than that.

[ExpatInItaly]

Well, you tried, OP. 

And now you know that she's not really interested in being more than friendly coworkers. She didn't lead you on. She simply sees you as work buddy. Yes, she could have acknowledged your invite for drinks. But perhaps she felt awkward and isn't one of those people who is ballsy enough to say "no, thanks" - especially when you still have to work together. 

 

[smackie9]

Sharing deep conversations is not intimacy or a sign of romantic interest. That's workplace bonding. I have been at my job for over 34 years. I have all kinds of employees talk to me about very personal stuff. Usually ends with, please don't say anything about it to anyone. And I do just that. The only reason she is talking to you like that is because she trusts you. That's all it is. When a female is nice, warm, friendly, doesn't always mean she wants you.