Asking her out over text - what's the best possible way?

[Smartone84]

To summarize this story from a previous thread: Have been slowly getting to know a co-worker for the last 6 months. To be clear- We do NOT work in the same office. Just the same company. I only end up stopping by her office occasionally, once every few weeks or so, which is why the progression of all this has taken time. Each conversation we've had seemed to progress well. I even waited to see if she came to me to talk and on a few occasions she did. Our convos have ranged from 10 minutes all the way to one that was 45 minutes long. We have great conversation chemistry and talk about work, family, hobbies, etc. I make her laugh a lot. As time went on, I began to throw in a few subtle flirty comments. She's a very timid and reserved type, so I only ever got laughter and smiles as a response. She has never flirted with me or given me any real confirmation that she's interested me on a romantic level. All that said, I'd estimate that it's a 50/50 chance that she's into me in that way. Recently it seems like she's even more happy to talk to me than ever and is always interested in stuff I have to tell her. She also has a close friend at work who I happen to work with a bit more that I've gone out of my way to be nice to. I told this friend to tell her (the chick I like) I said Merry Christmas. I was then told by the chick I like that she got the message as she smiled. Would be hard to beleive the friend delivered the message without mentioning something else about me (its known that I'm single).

The problem is NOTHING at all has come easy for me with this woman in all of these 6 months. Nothing. I had hopes to finally see her outside of work (and progress much more) at my companys Christmas party, but she was unable to attend. I didn’t ask her to go, but she had told me this beforehand and said she would’ve gone. I also once (semi sarcastically) said to her that once she gets a promotion we'll have to get drinks to celebrate. She laughed and said ok. That was 5 months ago now and she unfortunately has yet to get promoted. Also, while I work 8-4pm, she works nights and gets off at 9pm, so me going by her office (which is an hour away from my home) for a happy hour at night is basically out of the question. Lastly, she lives over an hour away from me in general, so its not like I could casually mention a bar near me that I wanted to check out, asking her if she wanted to join me. So now I'm at a point where its basically ask her out for one night on her day off or bust. Finally last week we exchanged numbers. I told her to put her # in my phone and she quickly and seemingly gladly did. I have never texted her yet and all of our convos have been in person, of course. She's 29, so she's definitely a phone person, so I'm thinking that I'm just going to get things over with and somehow, someway ask her out over text, even if its indirectly. As well as we now know each other, I'd be lying if i'm still not quite there yet as far as being comfortable enough to ask her out in person at work. Not only because its at work, but because again, she's just never given me any real signs that she wants to go there, so if in the event she's not into it, the text would be a lot less pressure for her. (me too, mind you)

Bottom line is I'm well aware this could all just be a very nice woman who enjoys talking to someone at work from time to time, but I still beleive there's a good chance its a little more than that. In my experience, most single women at work with no interest at all be sure to keep their distance from other single guys. She's never done that. Only me finally asking her out will let me be able to tell, but I want to do it right and not cringe. Any and all advice is appreciate. TIA

 

[New_Journey]

To be clear- We do NOT work in the same office. Just the same company

Doesn't matter, its the same company, this is not good

She has never flirted with me or given me any real confirmation that she's interested me on a romantic level

Not a good sign.

I'd estimate that it's a 50/50 chance that she's into me in that way

Its better to think lower just in case.

but she was unable to attend

Another sign that is not good

ask her out over tex

This is foolish and $tupid. The moment you start texting on a romantic way, its the moment where she potentially has all the ammunition to get you in trouble with the company.

As well as we now know each other, I'd be lying if i'm still not quite there yet as far as being comfortable enough to ask her out in person at work. Not only because its at work, but because again, she's just never given me any real signs that she wants to go there, so if in the event she's not into it, the text would be a lot less pressure for her. (me too, mind you)

This is the only way you can have some plausible deniability, it would be her words against yours.

Any and all advice is appreciate

On a Friday night without any prior anticipation, you go to her and ask "you got plans for tonight after work? there is a nice sushi restaurant I found and I'd like you to join me"

No text, no evidence. Guys think work texting is harmless until it blows up in their faces.

 

[Smartone84]

Another sign that is not good

with regard to the Christmas party, for what it’s worth, I didn’t actually ask her. She told me she had plans that night weeks earlier when we were discussing it. She actually said she would have liked to go.

Also, I don’t really see how asking her out once via text is “foolish and stupid” and would possibly land me in trouble with HR. Guys that get in trouble for stuff like that at work are idiots who can’t take a hint and keep bothering women. On top of that, I’ve known this girl for 6 months now. Trust me when I say- she’s not that type.

 

[Clockwerk50]

As I mentioned in your previous discussion, it seems like you're overthinking and analyzing the situation a lot, especially considering you haven't even had lunch with this person yet. It's not necessarily wasted time, but this level of insecurity might have unintentionally placed you in the "friend zone." You come across as that cute, cuddly friend who is nice to talk to, but there doesn't seem to be any sexual chemistry. Confidence and self-sufficiency are typically seen as attractive, whereas self-consciousness and insecurity aren't. You may be too outcome-dependent, focusing on saying the right words to get her to say yes to your invite, but that doesn't necessarily signal romantic interest. It's a classic case of oneitis, where you're putting all your emotional energy into this one person, which can cloud your judgment and prevent you from seeing things clearly.

From what you've shared, it sounds like you'd be upset if you stopped talking to her, but she'd be okay with it if the relationship ended. In my experience, if a woman is interested in a romantic connection, she would typically give you subtle cues to move things to a more intimate level. Based on your story, I'm not sure if that’s been the case here, but it’s definitely something to look for moving forward. Pay attention to how she responds to you and whether she's offering hints that she wants the relationship to evolve. If you’re still stuck in this “oneitis” mindset, it’s crucial to break free and consider your own emotional independence.

Are you talking to more women? Are you going to the gym and working on improving yourself? Sometimes, the best move is simply to ask her out directly so you can either move forward or move on. It will help you clear the air and give you the opportunity to focus on what’s truly important for your own growth and happiness. Break free from the idea that this one person is the only option for you.

 

[Smartone84]

As I mentioned in your previous discussion, it seems like you're overthinking and analyzing the situation a lot, especially considering you haven't even had lunch with this person yet. It's not necessarily wasted time, but this level of insecurity might have unintentionally placed you in the "friend zone." You come across as that cute, cuddly friend who is nice to talk to, but there doesn't seem to be any sexual chemistry. Confidence and self-sufficiency are typically seen as attractive, whereas self-consciousness and insecurity aren't. You may be too outcome-dependent, focusing on saying the right words to get her to say yes to your invite, but that doesn't necessarily signal romantic interest. It's a classic case of oneitis, where you're putting all your emotional energy into this one person, which can cloud your judgment and prevent you from seeing things clearly.

From what you've shared, it sounds like you'd be upset if you stopped talking to her, but she'd be okay with it if the relationship ended. In my experience, if a woman is interested in a romantic connection, she would typically give you subtle cues to move things to a more intimate level. Based on your story, I'm not sure if that’s been the case here, but it’s definitely something to look for moving forward. Pay attention to how she responds to you and whether she's offering hints that she wants the relationship to evolve. If you’re still stuck in this “oneitis” mindset, it’s crucial to break free and consider your own emotional independence.

Are you talking to more women? Are you going to the gym and working on improving yourself? Sometimes, the best move is simply to ask her out directly so you can either move forward or move on. It will help you clear the air and give you the opportunity to focus on what’s truly important for your own growth and happiness. Break free from the idea that this one person is the only option for you.

Thank you for your lengthy response. To answer a few questions and to make a few points:

-She is absolutely not the "only option for me". I am talking to several other women, but, I'd be lying if I didn't admit that the subject woman is more of a priority as I feel the nicest connection when I speak to her.

-With the above point said, by no means would I be heartbroken if this ended tomorrow and I stopped talking to her. Disappointed yes, but the next morning I'd be ready to move on. As a matter of fact, even it would actually be a good thing either way for me, as if she rejects me then at least I get to move on and not worry about her anymore.

-The only reason I'm overanalyzing this all is because of the work factor. That is it and that is all. If this were a girl I met through a friend or out at a bar and she was being super receptive to me without showing any blatant signs of romantic interest like this girl is doing, I would still ask her out on day ONE and get it over with. This girl is a co-worker at the end of the day. I've never asked anyone from work out in my life and for good reason. It's just not something that people should be doing at the drop of a hat. You really have to know you like said co-worker imo before you go there. I don't want to make things uncomfortable for her if she is infact not interested, so yes, I've allowed a lot of time to go by to see how things have progressed. They've progressed quite nicely but unfortunately I've never gotten that "A ha!" moment of getting confirmation she has romantic interest. That being said, I still strongly stand by my estimation that this is a 50/50 chance. But that still means 50% chance of rejection, so again, I want to make sure I ask her out in the most nonchalant, low pressure way so there's little to no awkwardness when its over.

 

[Clockwerk50]

Thank you for your lengthy response. To answer a few questions and to make a few points:

-She is absolutely not the "only option for me". I am talking to several other women, but, I'd be lying if I didn't admit that the subject woman is more of a priority as I feel the nicest connection when I speak to her.

-With the above point said, by no means would I be heartbroken if this ended tomorrow and I stopped talking to her. Disappointed yes, but the next morning I'd be ready to move on. As a matter of fact, even it would actually be a good thing either way for me, as if she rejects me then at least I get to move on and not worry about her anymore.

-The only reason I'm overanalyzing this all is because of the work factor. That is it and that is all. If this were a girl I met through a friend or out at a bar and she was being super receptive to me without showing any blatant signs of romantic interest like this girl is doing, I would still ask her out on day ONE and get it over with. This girl is a co-worker at the end of the day. I've never asked anyone from work out in my life and for good reason. It's just not something that people should be doing at the drop of a hat. You really have to know you like said co-worker imo before you go there. I don't want to make things uncomfortable for her if she is infact not interested, so yes, I've allowed a lot of time to go by to see how things have progressed. They've progressed quite nicely but unfortunately I've never gotten that "A ha!" moment of getting confirmation she has romantic interest. That being said, I still strongly stand by my estimation that this is a 50/50 chance. But that still means 50% chance of rejection, so again, I want to make sure I ask her out in the most nonchalant, low pressure way so there's little to no awkwardness when its over.

The best way to ask her out "nonchalantly" and avoid any potential awkwardness would be to ask her outside of work, but still during work hours—like for a casual lunch at a chain restaurant. This way, you're not mixing personal and professional time, and it feels more relaxed. You should also give her an easy out in case she's not interested, like saying, "If you have a meeting or something around that time, no worries at all." This keeps the pressure low and allows her to decline without discomfort.

The same principles as with dating outside of work apply: if she cancels and doesn't reschedule or offer another time, it's likely she's not interested. Hopefully she says yes and insinuates that she wants to pursue a romantic relationship with you.

Good luck!

 

[Smartone84]

The best way to ask her out "nonchalantly" and avoid any potential awkwardness would be to ask her outside of work, but still during work hours—like for a casual lunch at a chain restaurant. This way, you're not mixing personal and professional time, and it feels more relaxed.

If by this you mean like during a lunch break, unfortunately that is not possible as we don't take breaks at the same time when I'm in her office, and to make matters worse, the office is also in an area where there is no restaurants at all within walking distance. If we BOTH worked a straight 9-5 and took lunch around the same time and there were go-to spots right next to the office, then yes, that would probably be the best case scenario. But like everything else with this girl/plate, nothing has come easy. Are you completely against me asking her out via text in some form?

 

[Divorced w 3]

Doesn't matter, its the same company, this is not good



Not a good sign.



Its better to think lower just in case.


Another sign that is not good


This is foolish and $tupid. The moment you start texting on a romantic way, its the moment where she potentially has all the ammunition to get you in trouble with the company.


This is the only way you can have some plausible deniability, it would be her words against yours.


On a Friday night without any prior anticipation, you go to her and ask "you got plans for tonight after work? there is a nice sushi restaurant I found and I'd like you to join me"

No text, no evidence. Guys think work texting is harmless until it blows up in their faces.

There is nothing wrong with casually screwing a colleague. I did it over the summer, she works in the building but 30 floors above me. There is virtually no running into each other. You just need to be cool. I would recommend a couple texts that imply mutual consent but that’s it.

The way I asked her out was the following: we met in the late spring, a week or two later I got a coffee with her at the building cafe, totally innocuously and we just kind of left off that we would catch up soon.

Maybe like 3-4 weeks later I ran the usual script: teams message (bc it was internal) - light chit chat for a couple minutes, determined her wearabouts for the next couple weeks and then shot my shot, said something like ‘Thursday, drinks at Tao 4:30 after the close?’ - she said how about 5, and within an hour of sitting down she was coaxing me back to her place.

 

[Smartone84]

The way I asked her out was the following: we met in the late spring, a week or two later I got a coffee with her at the building cafe, totally innocuously and we just kind of left off that we would catch up soon.

Maybe like 3-4 weeks later I ran the usual script: teams message (bc it was internal) - light chit chat for a couple minutes, determined her wearabouts for the next couple weeks and then shot my shot, said something like ‘Thursday, drinks at Tao 4:30 after the close?’ - she said how about 5, and within an hour of sitting down she was coaxing me back to her place.

Very nice. Natural way of things progressing with an office chick. Now if only her (our) office had a building cafe or anything at all just a few steps away, I would have sped up this process months ago now. Instead here I am having to figure out how to ask her out for a legit date which really can't be anything but on her day off. (she works nights, until 9pm as I mentioned above)

 

[New_Journey]

There is nothing wrong

Yes it is, its something very wrong, it only takes her to get annoyed or jealous, go to HR and show some mild flirty text and she saying "this is inappropriate and I feel harassed, he passes by my desk multiple time per day, I feel harassed and not in a safe environment"

You never $hit where you eat. People think its nothing wrong until it blows up in their faces. That's just my two cents, he can do whatever.

 

[Divorced w 3]

Yes it is, its something very wrong, it only takes her to get annoyed or jealous, go to HR and show some mild flirty text and she saying "this is inappropriate and I feel harassed, he passes by my desk multiple time per day, I feel harassed and not in a safe environment"

You never $hit where you eat. People think its nothing wrong until it blows up in their faces. That's just my two cents, he can do whatever.

It’s virtually impossible to do what you’re suggesting and I have texts that show mutual consent. It is also cross department meaning we can’t be accused of anything untoward in the same division.
Want to know another fun fact, her boss is doing substantial business with me; neither of them know it.

 

[Smartone84]

Yes it is, its something very wrong, it only takes her to get annoyed or jealous, go to HR and show some mild flirty text and she saying "this is inappropriate and I feel harassed, he passes by my desk multiple time per day, I feel harassed and not in a safe environment"

You never $hit where you eat. People think its nothing wrong until it blows up in their faces. That's just my two cents, he can do whatever.

Maybe this could be a possibility in a close tight office, but I don't even work in her actual office as I noted. I pass by her desk to talk on average of once every 2-3 weeks, and beleive me I would stop at the first millisecond she showed disinterest in conversing with me.

 

[Clockwerk50]

If by this you mean like during a lunch break, unfortunately that is not possible as we don't take breaks at the same time when I'm in her office, and to make matters worse, the office is also in an area where there is no restaurants at all within walking distance. If we BOTH worked a straight 9-5 and took lunch around the same time and there were go-to spots right next to the office, then yes, that would probably be the best case scenario. But like everything else with this girl/plate, nothing has come easy. Are you completely against me asking her out via text in some form?

Plates are typically categorized as women you're currently having sex with.

To be honest, your two options for asking her out are either going after your shift and asking her in person or sending a low-pressure text, like suggesting coffee or lunch, something that avoids too much pressure and allows her to decline politely.

However, I think the whole situation is too chaotic and works against you for this kind of investment. The long commute, her working nights while you have a standard day shift, and the lack of nearby restaurants or places to hang out near the office all make casual interactions difficult. There’s also the issue of not having the same break times, which means even small interactions require more effort to set up. Add in her reserved nature, the uncertainty of her romantic interest, and the fact that you’re in a professional setting, where any awkwardness could affect future work interactions, and it makes this situation even more complex. If she's not giving clear signals, this could lead to misinterpretation and unnecessary discomfort, especially since there’s no natural opportunity to connect outside of work. It sounds like a nightmare for you if you start a relationship with her.

Why don't you move on to other prospects that live closer to you and where there are less hurdles?