If she had romantic interest, she would not be reacting this way (i.e. pretending that your suggestion was a joke when she obviously knew that it wasn't). You are on shaky ground pursuing a coworker who likely isn't interested. This could end up being a career-ending move. Think with your BIG head before pushing this further.
There will be always a woman to whom you will always be a creep. You cannot change that and you will not know who she is until she files paper work on you.
No... it's not just about asking her out.. basically, lets say the majority of us here are wrong - she does like you; lets assume you ultimately get your Richard wet, what happens if the relationship goes south, how do you know she will not want to get even? Or worse???? You barely know this woman as you noted, you only see her once a month. "simply asking her out".. yeah, right.. Relationships are messy.. you have been at your current job for a long time -- 17 years. Do you really want to risk this job where you seem comfortable and like, for some tail?????? To most rational people, it's just not worth it.
Saying "No pressure" = pressure. I think someone said this the other day in another thread but its true
While I really am fond of this girl and genuinely do think we have solid chemistry, I'm also willing to admit that yes, a scarcity factor is responsible for a lot of what is going on. I just turned 40 and for a number of years now, dating and meeting new women has almost been entirely isolated to one place- the dating apps. It has just been beyond refreshing to actually engage with, get to know and be interested in someone in person for a change and not just photos on my iPhone. If I was still in my 20's or maybe even early 30's and was spinning multiple plates or had 3 numbers in my phone I still didn't contact yet, then yes I more than likely wouldn't be as worried about how to game a girl at work or how to proceed next, etc. All that being said, one good thing about being this age and having a lot of dating experience is again, I do in fact think there is something there between me and this chick. Whether or not we end up on a date one day I can't say, but I'm still comfortable at least trying.
I can understand this. I think adding on something along the lines of "In all seriousness there's not even a need to give an answer if you're not comfortable doing so" to double down on your no pressure statement to make her that much more convinced.
I wouldn't say walk in the park. The issue at hand is the fact that this is a workplace pickup and it's something I don't really have much experience with at all. I don't think I've ever actually asked out a co-worker since my teenage days working as a cashier at a supermarket. This here is a much different ballgame imo. It would obviously be a lot easier if she gave me all sorts of IOI's or even hinted at going out but there's been nothing of the sort. Only very nice conversations, tons of laughs and smiles, and while that might sound good on paper, still poses as an uphill battle once you are within the confines of the workplace. Because you see, even if she rejects me, I want to do this in such a way that I don't look like a goof and we can just move on like it almost never happened.
Yes I agree its absolutely better, and in a perfect world a work happy hour would be the thing. Hell, I probably wouldnt have even made this thread as it would be the obvious option, but I don't even work in her office to begin with (only there occasionally), and I know for a fact they don't even do things like that. We have a company Holiday party in December. Not everyone goes. That's something I could theoretically ask her to go to, but even that is months away.
You're making this a bigger deal than it needs to be. The more pressure you add, the more significant the issue becomes for both of you. If you had enough experience with dating, you’d realize how insignificant asking someone out can be and how frustrating it is to go on a lunch date, especially when you're not genuinely interested. Women are often better versed in this game, and if they reject you, they typically act like nothing has happened as long as you get the hint and stop pushing.
She is 28 and single. We have never spoken about dating or anything of that nature at all. For all I know she might not be into dudes. The convos have been 95% work and hobby related.
Reading that paragraph, Sun Tzu's 'every battle is won before it's ever fought' came to mind. You should be certain she says yes before you make the invitation. I mean, you've been talking for a year now, plenty time to assess her.
Then how do you know she's single? Maybe she's in a 'it's complicated' type of situation.
Create self-fulfilling prophecies. Always assume the positive. Assume she likes you. Assume she wants to talk to you. Assume she wants to go out with you. When you think positive, positive things happen.
Quote taken from The SoSuave Guide to Women and Dating, which you can read for FREE.
First, I know she's single because I overheard her answer someone about the topic a while back in a casual group convo at work. I forget if relationships were being discussed or what, but it came up. Second, relationship talk hasn't come up between us because again, first of all we only chat about once a month on average and 99% of our convos have been about work or hobbies. Basic stuff. I crack a lot of jokes with her and make her laugh, but it really was only until recently where I got even the slightest bit flirty. I think this is also why I'm quite hesitant about how to ask her out, because truthfully, unless it happens organically with the celebration drink I originally mentioned to her, I think it could be a bit awkward. I like things that feel natural. Given the fact that she's never really given me much at all to work with IOI wise, idk, maybe its best to let things simmer a bit more and see how it progresses...Reading that paragraph, Sun Tzu's 'every battle is won before it's ever fought' came to mind. You should be certain she says yes before you make the invitation. I mean, you've been talking for a year now, plenty time to assess her.
Then how do you know she's single? Maybe she's in a 'it's complicated' type of situation.
I also find it strange that you've been talking all this time and her relationship status hasn't come out naturally in the conversation.
Yeap, let things simmer for another year,that definitely will improve your chances with her,,,,
"Yo... I'm grabbing coffee at (insert time). Join me. We've much to discuss"
Id be real careful what you put on teams. A lunch offer is probably ok but id get her number after that and not use teams and get her number
Yea, you are right. Even the taking the same vehicle is a little too much when it is preferable to meet at the venue.
