Another comment - I know some people will be tempted to say “women like a man who is confident or agressive or …” Remember that women, like men, are all different, and what one woman views as confident and self-assured can seem to the next woman as an obnoxious jerk. Don’t be afraid of asking someone out, but don’t start changing your whole personality either. If you are interested in a woman she will eventually realize it, especially when you say so. It never hurts (IMHO) to verbalize your feelings and say outright what you’re thinking. When asking a woman out on a date, if she says “is this a date?” don’t answer “of course it isn’t, we’re just friends”; say something like “well I hope it is” or “I would like it to be.” If at the end of the evening you had a good time and would like to see her again, then you can go ahead and tell her that. If on the other hand you decide you want to just be friends sharing a common interest, tell her that too.
Finally - even though another cliche is that women like a man with a sense of humour, don’t start imitating a gorilla in the middle of your dinner at a fancy restaurant. Trust me, that never works.
This would have been of great use to me YESTERDAY.
Excellent question that brings no answer immediately to mind. I think part of it was a strict Irish Catholic upbringing. Part was having parents who NEVER once had a conversation with me about the “facts of life”.
And then there was my childhood living arrangements, which I don’t know a term for, but I’ll give you a description… this is a path I did not want to travel on when I started this thread.
I have two older sisters, two and thee years older than me. We lived in a three bedroom house; my parents room, my sister’s room, and mine. As we entered adolescence, my two sisters became intractable enemies, for what reasons I still don’t know. They fought, verbally and physically, constantly. By the way, my childhood was also chock full of screaming rages by my father, who would go off at the drop of a hat. We stepped lighly. My parents decided to swap roommates, and at age nine or ten I ended up sharing a room with my oldest sister, and we shared a bedroom until she moved out at age eighteen. My oldest sister was THE hottie of the neighborhood. You better believe I learned to suppress.
In all of grade school and highschool, I never once participated in an extracurricular activity. Never went to one dance, one game, one anything. My dad’s refusals to do things (or let me do them) were always emphatic and blanket. All that stuff was a waste of time and money. The one exception was when I was literally blackmailed by a highschool speech teacher into competing in a regional speech tournament, and to my great surprise did fairly well.
So in the RW, I am (or was), 100%, the calm in the storm. No matter what, I never fluster, raise my voice, stop thinking of solutions to the moment’s problems, lose control. I am a very bright guy with a very powerful ability to closely focus on small things, and deliberately ignore (perhaps devalue is a better term) large parts of reality.
I have NEVER successfully picked up a woman, or if you prefer a more PC description, I’ve never had a sexual relationship with a woman that I’ve known casually, liked, and the tried to become a lover to with in mutually agreeable ways. I have tried, a few times, an intellectual approach that has always failed miserably.
Fortunately for my own sanity, I HAVE been picked up by a few women in my life, who’ve been agressive enough on their own to come after me. A couple of those relationships have lasted a year or two.
I’m sure you’re right. But my question isn’t, “What will happen if I ask her out?”, but more “Why do I NOT ask her out?”. Somewhere back in time, I can’t say when, I hit my rejection limit. I just don’t want any more.
I have considered getting some therapy or counseling about this. Actually, considering my own terminology above seems akin to some kind of battle fatigue, I’m talking myself more in that direction even as I write.
But I have my doubts. The two psychologists I’ve known personally, I wouldn’t trust to feed my cats.
No, I don’t think so. I think I fear my increasing sense of desperation. I think I fear becoming a mole, and I’m doing a few things to not be one. But really, if there was a decent library and enough smokes, I’d be perfectly comfortable in solitary confinement in prison. Or at some not too distant point in my life I would have been.
What if it’s a fancy restaurant with a jungle theme?
Straightforward advice if ever I saw it. 
This whole thread is comforting. It may sound odd, but it’s nice to know there are guys in their 40’s out there who are worse around women than me. But I’m living proff that anyone can improve.
Good luck!
Gundy, thanks for your many kindnesses, in person and online.
“…Sort of like talking to my male boss - which is far nicer than it sounds. I was comfortable talking to you because you weren’t (obviously, at least) checking out my boobs.”
That is it to a tee. I can be broken out of it but I cannot break myself out of it.
Perhaps you remember a certain ChiDope Timmy O’toole’s breast groping incident? You were nearby. And the question I asked? And the response I got? There were several comments from among the assembled Dopers that when it came to social breast groping (for the life of me I can’t think of a better term :p), a guy should just go for it rather than ask permission. I’m not that guy, and you witnessed the results. I’m the guy that asks, and doesn’t get permission.
By the way, thank you all very much so far for your comments and support.
It is Friday night, and I wimped out on my one brief opportunity to ask her out, but it would have been in public, in the workplace. I wasn’t willing to do that.
Our schedules are such we DON’T have more than a minute or two to chat. She’s there one-half a day a week (Friday afternoons, the rest of the week she works in another clinic), and gets there maybe 5 minutes ahead of her 1st patient. She’s in about 1 PM having already had lunch, I’m out of there by 3 PM (and have to arrange the weekend events before I leave, so I have a very busy afternoon).
Also, several of you have said she’s hitting on me, or at least sending encouraging signals. This is a birthing center, a very touchy feely place. At a recent goodby dinner for a staff member (Pat, interestingly, who was going to leave but was talked into maintaining a minimal presence to keep the clinic open), I was the only male at a table of 23. These women routinely hug each other, and hug me. (Well, I get hugged at least once every couple weeks). And everybody expresses fondness and appreciation for each other verbally, it’s kind of an ethos there. Most of them are into Motherhood and Sisterhood on a somewhat philosophical level. It really has a kind of “activist” atmosphere at times, which I find refreshing after a brief (and spectacularly unsuccessful) dip into the private sector.
So it is not so apparent to me that Pat was sending out “come ahead” signals as far as a personal relationship goes, let alone an intimate one.
yojimboguy, ask her out on a date. Say, “How about getting something to eat tonight?” If she says yes, the world is your oyster. If she says no, you only have to see her once a week.
I think Pat is sending you signals. I am a very touchy-feely person, but I would never combine the arm-touch maneuver with the loaded comment unless I was interested in a man. Oftentimes, I do that - little gestures, comments, touching - to try to discern the man’s intent and subtly let him know I’m interested. If the man gives no response, I usually ask him out, but a lot of women aren’t into that, for whatever reasons. I’m guessing she’s waiting for you to make the move. So just knock on the office door, ask her out, and see what happens. It truly will not be a big deal if she says no; believe me. It will sting a little, sure, and you might dwell on it for a day or two, but by the time next Friday rolls around, you won’t care.
We’re not so different, you and me. And sometimes I get so fed up with trying to have something I’m not sure I want, that I convince myself I don’t want it - that it’s not worth it, it’s a waste of time and energy, it’s too much work. And I believe that for so long that putting myself out there is scary, painful, and embarassing, and I long to go back to my library and chain smoke. I know for a fact that I can go through my life like that - alone, with smokes and books - and be content and even happy. But I always manage to convince myself that it is worth the risk, and I think you need to convince yourself of the same thing.
I don’t care how much into Motherhood or Sisterhood or whatever she is - before I got married, I wouldn’t tell every male friend that I’d hug that they could have whatever they wanted, and then not brush it off when ‘called’ on it jokingly.
I’m not saying it’s 100% sure that she’s hitting on you, but I’d say it’s extremely likely. And anyway, I’d say it’s worth a shot to at least try to get more friendly. 
yojimboguy here’s the scoop. You said:
That is EXACTLY how I feel about things. Before we were dating, my current beau was pretty much EXACTLY as you just described yourself and I totally ate it up. I did pretty much all the pursuing, all the asking, all the ogling. Finally…FINALLY, he got the picture and now we’re happy as clams.
IMHO, Pat is doing some persuing, asking and ogling here -throw the gal a bone, man! Next time she’s in her office just say “Hey - I’m heading over to the cafeteria for coffee/lunch/snack - care to join me?”
yojimboguy, you were really a great guy in person. I’m sure you’ll do fine with Pat. Just let us know so we can get all adolescent on you and start in with the “yojimbo’s got a girl-friend” chants.
And that picture was great, it looks like your head is about to explode from keeping your hormones in check. Gundy is a cutie even if she can’t take a decent picture to save her life! 
Yojimboguy, that was a very interesting response to my queries. So, you would almost be happy in a library with enough smokes, eh? Maybe you’re an asexual (not that there’s anything wrong with that). Do you feel like it is so hard and risky to develop relationships with women that you don’t feel like making the effort anymore? I’ve heard it said that once people get into their forties they’re well on their way to becoming set in their ways. (Here’s me taking a WAG again) - are you conflicted about what you want? Are you not completely sure if you want a relationship or not?
You go, dude!
And, Good Luck.
Dare to eat a peach.
And wear your trousers rolled.
I hear echoes of Seinfeld. No, I’m not. However, I have lived in that manner for most of my life, and I don’t want to anymore.
[/QUOTE]
Do you feel like it is so hard and risky to develop relationships with women that you don’t feel like making the effort anymore? I’ve heard it said that once people get into their forties they’re well on their way to becoming set in their ways. (Here’s me taking a WAG again) - are you conflicted about what you want? Are you not completely sure if you want a relationship or not? **
[/QUOTE]
Oddly enough, I’ve heard you’re set in your ways by about age 10. I hope I’ve learned a few things since then. My conflict is that I don’t want to wait for a relationship to come to me, yet I have this terrible fear of rejection. Not social rejection, but sexual rejection.
And to be more specific, it’s not simply a “relationship” I want, but one that includes sex. And that’s where my social skills completely fail me, in the transition between casual aquaintanceship and intimacy. The only say I’ve ever been able to attempt this is to talk about my feelings straight out, and the responses have been universally negative. Have you ever simply talked a woman into sleeping with you, without having so much as touched her first? I haven’t.
You’ll need a shiny quarter attached to a string.
"Loooook at the shiny quarter swinging back and forth … you’re getting sleepy … sleepy … sleepy … "
Hey, the farmers market just started. The next time you see her ask her if she went, I’m betting she didn’t because it was so lousy out. Then tell her all the good things you can buy, coffee, etc and when she acts interested (and women I know just love it) ask her if she wants to go with you the next time.
If she doesn’t like it, well, my plans aren’t always perfect, which may explain why I’m not maried.
If that doesn’t work, tell her you’re a Doper, that should wow her!
Oops. Here’s the rest of the post. Sorry.
Buddy, there was a LOT of breast groping going on. You’ll have to be more specific. I recall someone asking to grope my own personal breasts, and I declined, but I don’t think that someone was you. Mainly I remember Persephone’s breasts.
Outside of the dopefest bubble, who asks to grab someone’s breasts and gets to anyway? I’ll tell you - no one.
You know what? You remind me of my boyfriend. He’d always had plenty of female friends, but making the transition from friend to more-than-friend often failed for him. He was worried about being a jerk, basically - people encouraged him to be more aggressive, but he couldn’t without worrying he was overstepping his bounds. On top of that he’d dealt with his share of rejection and was gunshy. Once I became interested in him, I had to be a little more aggressive myself than I was used to (as, it seems, Pat may be doing). We both took baby steps for a while before the dating thing really went anywhere.
Must…fellate…Snooooopy…