What is a clever/low pressure/indirect way to ask out a co-worker?

[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 November 28 by Mac0908

[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 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 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.