Lucky you.
I think the main misconception is the idea of a pickup, and that one person must necessarily be the initiator.
My dating experiences got a lot better when I rejected all that hollywood crap and just got in the habit of talking to lots of people and throwing down subtle hints of interest in some people.
If she doesn’t take the bait, no problem. If she does, then we proceed to step 2 and asking her out on a date is maybe step 5.
In the end, it’s unclear who should be called the initiator…it’s more like a team effort 
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I should also say sometimes the actual “ask out” step is done by the woman, not me.
So yeah, I think two people getting together need to both contribute and who made the first move should not be important.
Social anxiety never kept me from not bothering women who weren’t interested; it was more likely to keep me from approaching those who were. Interestingly, I never had any problem interacting with women who I knew weren’t available; I never had any shortage of female friends. I’m certainly aware that social anxiety isn’t just a male issue. I’m sure the guidance you spoke of would help most people, but I always had trouble applying generalized advice to specific situations (for instance, when I took Algebra in school it always made sense when someone showed me what to do with a certain type of problem. I had a lot of trouble applying it to an almost identical problem). I don’t like to throw around words like “disability” and “disorder” lightly, but what I experienced certainly comes close.
I think what you’re trying to get at is that the woman’s the person at the tiller of the boat in this process, and men need to be more aware of how she’s steering.
The big issue is that picking up on how she’s steering things isn’t always so easy. Every woman’s different- one woman’s innocent flirting might be another’s invitation to hot monkey sex. And some women may come out and ask you out, while others may just show interest in the conversation and expect the man to pick up on it, AND interpret it correctly.
I kind of think the last part is the sticking point for most men- the interpretation part. Few men are so clueless that they are unaware of body language, or social clues, without having some condition like ASD or something. But lots of us have had difficulty interpreting them correctly for various reasons.
If nothing else, it’s probably better to play it cool.
But I also think it’s simplistic to assume that the woman is going to express interest in you in an obvious way or otherwise make the first move. She could be as nervous as the guy is. Or she may want some assurance that making the first move isn’t going to open the door to an annoying guy who won’t go away.
Or, conversely, a woman might just be naturally friendly and flirty, but that doesn’t mean she wants to sleep with you.
To echo what **Cheesesteak **said, it’s really time for society to reconsider this whole subtlety thing in light of #MeToo and just be more overt. Both genders are put at risk and danger by playing this maybe-no-means-yes-and-maybe-it-doesn’t-mean-yes game. Yes, I know, blatant overt “yes” and “no” may be unromantic, but safety and clarity ought to override whatever added romance may be had by playing games.
You are soooooo right.
I have this colleague who’s dropped what I consider clear hints of romantic interest almost as soon as we met. And I’m the sort of guy who’s really careful about interpreting such moves, so it was as blatant as it could be, short of getting physical. And then, at one point she became distant and I didn’t feel as welcome as before in her office. So I backed off, but it really affected me, and in November last year, after another series of her blowing hot and cold, I decided that it was better to stop seeing her (we don’t work together so that wasn’t too difficult). And I was doing all right. Disappointed, a bit wistful about the whole thing, but all right.
However, I came across her a couple of times as we arrived at work recently, and she always made a point of saying we didn’t “see each other anymore”. Then, just a couple of days ago, I entered a room where she happened to be and as soon as she saw me, she was all smiles, got up to talk to me and mentioned something that unambiguously proved that she’d been thinking about me in the meantime. So, after some inner deliberation, I suggested we had a drink together. Her face lit up immediately and she said yes three times in a row. Well, that was supposed to be today. I dropped by her office twice and she wasn’t there. No voice mail or email to cancel either. I finally sent her a neutral mail an hour later and she answered almost immediately with what sounds like “plausible BS”.
Seriously, I’m too old for this kind s***. I cannot avoid her completely as our company isn’t that big, but the problem is that she is so much my type it’s ridiculous, about my age and usually so affectionate when we meet that I just can’t help falling for it. If only she could be clear about all of this once and for all. It doesn’t matter whether it’s “yes” or “no”, anything would be much better than this constant hesitation. And I know I could ask her, but it would be awkward for many reasons.
If the dust ever settles without a clear answer, I’ll start a thread with a poll on the whole thing 
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Actual sexual harassment and having a woman be annoyed because a guy she isn’t interested in keeps talking to her are two completely separate things.
Well, things are moving fast.
She offered to make up for the missed drink by having lunch together. I accepted and only then did she mention that we were going to go with her coworkers. OK, not exactly what I thought but whatever, they’re nice. During lunch, she spent most of the time talking to them, the few times she turned to me was just for small talk. I’m starting to think that she only suggested the whole lunch thing because she felt bad about standing me up. Quite frankly, I would happily have done without.
At this point, I guess there are only three scenarios for what happened since we met, in decreasing order of likelihood :
1 - I was completely deluded from the start about what I interpreted as signs of interest, although - as I wrote above - some of them are very difficult to interpret otherwise.
2 - She was interested at one point but isn’t anymore.
3 - She is still interested but is doing a very poor job of expressing it.
Whatever the truth is, the best move for me is to forget about it altogether.
FWIW, I’m a woman and I have zero tolerance for games. They’re annoying. I would consider the suggestion of getting together for a drink to be sex-related, as it is not a real date. This might be a tempting offer at some future time – say, Saturday – but it could be affected by any number of issues that might arise by Saturday. Because life is like that, especially when you’re planning for the possibility of someone else involved in your body on some specific date. Upon acceptance of your…offer, now there are expectations, due to her expressed interest in “going out for a drink”. And now we get to guess whether your “romantic” interest involves anything beyond fucking, because that’s the game you’re playing.
Which is annoying.
But whatever, we’re all different. Sometimes things are ambiguous. You could try asking her out on a proper date, and you might get a proper answer.
I think this phrase hits the nail on the head. You want her to be clear and unambiguous, but you’re not willing to clearly state what you want for fear of awkwardness. Maybe she’s trying to avoid the same awkwardness, and doesn’t know how you feel.
That said, anybody who consciously, or deliberately, sends mixed signals has only themselves to blame if they’re not received correctly. It’s becoming less and less acceptable for men to pursue women who are reluctant. Along with that comes the responsibility for women to be honest and to put in some of the work to make things happen when they are interested.
Well, one of the main reasons is that she’s extremely serious about her work. Introducing this subject on the workplace is going to be awkward as hell for both of us and I sure don’t want her to feel uneasy. I also want to point out that I’ve never found myself in such a situation there. I’m definitely not known to hit on my colleagues. My workplace is about 70% female and it was the very first time in my 15+ years there that I thought “OK, something’s happening here.” Over time, I’ve managed to find innocent meanings to most of the things she told me but I’m down to a dozen that I cannot interpret in any way other than signs of romantic interest, no matter how hard I try to handwave them away.
Anyways, what I don’t get is this constant flip-flopping. As I said above, the standing-me-up and barely-talking-to-me-during-lunch things should be obvious messages. But I also heard her say something extremely positive about me to her coworkers at one point when I was coming back to the table after leaving for a short while. There was no point of saying anything good in my absence if she didn’t mean it.
Also her happy reaction two days ago, when I offered to go for a drink looked 100% authentic. Either that, or I really need to go live a cave because there’s no way I can misunderstand someone’s facial expression so completely. I know some people have a hard time saying “No” for fear of disappointing others but there’s an unmistakable difference between a half-hearted “Sure…” and her “YES !” (x3).
Finally, I’ve been thinking about her reason for not being in her office this morning when we had agreed to meet and I don’t think it’s BS after all. She’s far too serious about her job to come late just to avoid me. But I don’t understand why she didn’t just let me know. That is so not like her, as she’s always been considerate, even in her “blowing cold moments”.
As I’ve said, I’ll back off once more, hopefully for good this time. I really don’t see how anything good could come out of this, and I respect her to much to cause her embarassment.
Still, for a while there, it felt so good…
So once again, we have a man who decries game-playing by women but refuses to lay his cards on the table because it might be awkward if he doesn’t have a winning hand.
It sounds to me like she’s actually successfully communicated to you that she feels similarly to how you feel: interested but uncertain, and afraid to mess things up at work. You have a couple choices here. One: you can lay it all on the line. Tell her you’d like to take her on a date, in so many words; none of this face-saving let’s-get-a-drink-after-work prevarication. (I’m faithfully monogamous and I get drinks with co-workers, even male co-workers, all the time. But if one of them asked me to go on a date, I’d say no.) Two: you can stay the course and drop the “I hate games” BS. Because you’re playing games as much as she is, because they serve your interests of maintaining plausible deniability while sussing out your chances. Or, to put it another way, you’re both slowly getting to know each other while evaluating whether the other is worth all the risks that come with dating a co-worker.
You say she is so much your type it’s ridiculous, but the only thing you’ve told us about her is that she’s about your age and plays games you consider yourself too old for. Do you mean she’s your type physically? If so, that would explain your hesitation to get involved given the stakes. If she’s your type in the sense that you really enjoy spending time with her, then why not just do that? Have lunch in a group, no expectations, no pressure, let nature take its course. Maybe in time one of you will change jobs and that will change the risk calculus in favor of asking for an actual date. Or maybe a low-key approach will give you time to actually fall in love, to the point you’re no longer worried about the awkwardness because you’d endure worse for a chance to be with her. Or maybe your crush will burn out, like so many crushes do. There’s nothing wrong with an honest wait-and-see approach. But you don’t get to default to that out of cowardice and then blame her for not taking the risk you refuse to take.
This is a strategy probably better left for a non-work environment. It would probably be seen as inappropriate to go up to a coworker and be this bold. There should be clear interest by a coworker before going to the next step. If the signs are vague or there is any question if she’s interested, then drop it.
@Esprise Me
There’s pleny of interesting points in your post but I want to make it clear that I don’t blame her for anything, and I don’t accuse her playing games. I’m just at loss to understand her signals - more, much more so than with any other woman I’ve met. Accuse me of being clueless if you want but not of playing the blame game.
We did spend a lot of time together last year, sometimes as much as an hour just chatting in her office. And as far as laying my cards on the table, I did tell her I liked her and she seemed touched. Then, after a while I thought I felt a distance in her. I respected that maybe she didn’t want to see me much anymore and I stopped dropping by her office. I’ve met her a most at dozen times this year, always by accident and I was fine with that. Nostalgic about what our relationship had been earlier but I accepted how it went.
Then, as I said earlier, she started mentioning how little we saw each other nowadays, that she’d been thinking about me and I found myself feeling like I had a year ago.
As Filmore advised, I’m going to drop the whole thing. Not out of misplaced pride but because she seems unsure about it and I don’t want her to feel uncomfortable.
Les Espaces, maybe she’s already in a relationship? She’s not totally happy but she goes back and forth about whether to end it or not? I agree, though, that the best thing to do for both your sakes is to let it go.
We haven’t talked about people’s ages. I did a lot of stupid stuff in my twenties because I hadn’t learned it was ok or how to say I wasn’t interested. I didn’t mean to play games, but that’s probably how it came off. My husband died last November and right now I don’t know when or if I’ll date. However, now in my fifties, I don’t want to waste my time or anyone else’s with BS. I’ll be kind, but I won’t be waffling around.
Too true. I lived in an all girls dorm through college and have had two jobs with mostly female coworkers, and the only time I’ve ever heard women say “I can’t believe he just gave up!” is in TV shows and movies.
It came kind of close to happening to me once. Someone told me that a woman we both knew wanted me to ask her out. I hadn’t thought about it, but I’d had several conversations with her and she was fairly attractive (plus I did enjoy talking with her). I called her up, and she said “I don’t know”. The next day our mutual friend wanted to know if I asked her out, and I told him what he said. I also said that I didn’t think she was really very interested, so I was going to drop it. Then I hear “she wants to be pursued.” I said that I didn’t play games, so that was that. The thing was, that weekend I went to a party and met the future Ms. P (who didn’t play games). I hope she figured out that saying that she was interested and then playing hard to get wasn’t the best idea.
I realize I’ve hijacked this thread with my personal anecdote, sorry about that.
To go back to the OP, it was definitely the case here. It took about 6 months of hearing her say and do things that I considered as “unusually affectionate” in a professional context or increasingly clear signs of romantic interest before I started considering that maybe something was going on. Nothing like it had ever happened to me in my female-majority workplace. Some playful banter or double-entendre with colleagues I’m a bit closer with, sure, but not such obvious hints. Apart from that, I’m on very good terms with everyone but tend to keep to myself.
So, in this case, it was definitely the woman doing the first move. But as I said before I’m starting to wonder whether I got it wrong from the start.
I’m in my mid-forties and she must be in her early forties for the record.