So does this mean I can actually GIVE advice, instead of only GETTING it?
I'll tell you two ways that worked for me, and one that won't, one in circumstances eerily similar to meeting people on/through the DISboards.
The one that won't anymore is DISmates. It cratered (or, as the pilots say, 'augered in') and left an empty hole in the Internet.
Quite a few years ago, I was in a Parrothead club (for fans of Jimmy Buffett, as if you didn't know). I'd been active for a few years, going on highway-trash-pickups, Manatee fundraisers and so forth. One of the gals in the club had been there longer than I had. We'd had several engaging conversations, but I never discerned any interest - the conversations were way too general ("Change the oil in your car yet?" "Yes - you?" "Changed it last month.").
One day at a picnic one of the other members called me aside and said "You know, X is really interested in you and you should ask her out." Somewhat startled, I thanked him for the aside, and shortly afterward asked X out.
That was a fairly safe way for someone to convey the invitation it seemed. I could have done what I did, or I could have said "I'm not really interested" and that message would have gone back down the pipeline. I can't tell you if X would have been hurt if I declined, because I did ask her out and we went out for a few months. (This is, in fact, the relationship that went sideways and caused me to throw myself out of the Parrothead club, because it became too uncomfortable to be there when she was there.) However, it would also be a good approach to use in that it insulates both parties from dealing directly with refusal should that be the result. Either way, I found it flattering that she would start the process of seeing whether I was interested.
Another way that worked for me is when Y asked me to join her for coffee a couple of times. It started fairly innocently (we both were at Starbucks near work during what seemed an independent visit, and after I sat down she came over and asked if I wanted company - actually, she said "Mind if I share the table?", which was indirect.), and then when I went for coffee, she said "Mind if I join you?" After the third or fourth 'coincidence' I asked her out. We had an enjoyable relationship, but trod carefully because it was at work. Unfortunately, she accepted a transfer to another part of the country so we broke up.
I can only speak for myself (and, looking at the length of this post, seem to do that quite a lot

), but often I feel as dumb as a box of rocks when it comes to a gal expressing interest in me. You might ask 'why?', since I'm so outgoing. I've learned that it's because I can never tell whether it's just interest because we happen to be in the same place at the same time and conversing, or whether it's someone who wishes I would take the first step with her. Said another way, I realize that not every woman I talk with is going to be interested in exploring a relationship with me just because she is talking to me. I really never learned the skills to discern when there is a greater interest than that. As Teresa noted above (and most men won't admit), it hurts when you are rejected. So, unless I'm pretty positive I won't get rejected I don't try to advance it.
The other thing is that I verbally flirt and tease a lot. I think I picked that up from my Dad. I also use that skill to defuse tension. But, even though I may be flirting with someone in which I am interested (as opposed just exercising my sense of humor), I've never figured out a comfortable way to make the transition from flirting to, for example, a dinner invite. So there probably have been circumstances where I've overlooked opportunities for connection that were there, but not readily identifiable.
For men to identify and understand a woman's interest is a tough task. They don't teach this stuff. I know we've all heard that when a woman plays with her hair it is supposed to express interest. I've also heard when a woman makes eye contact and then turns away, its supposed to express interest. Does it? Heck if I know.
This leads me to believe that there are two general approaches men use. One is what I might call 'the law of averages' method. That would be asking every woman out that shows even a micron of interest. Eventually, because you approach so many, you make some successful contacts. Perhaps men like this want to make a successful contact, and THEN see if there is enough interest to continue it. This doesn't appeal to me, because it means I would have to get pretty hardened to being hurt, because I'd get hurt a lot. The other thing is that it would make me appear to be a Casanova or, in this case, a troll. I'd probably be successful, but I'd leave a heckuva trail in my wake.
The other approach is more selective. The men in this group (which includes me) approach women in whom they see romantic possibilities or some sort of attraction, be it sexual, emotional, intelligent or whatever floats their boat at that point in time (and that's true for me, too - sometimes I see what to me is a really beautiful woman and I have a sexual/physical attraction; other times, I hear a woman express something for which I have particular affinity and I have an 'intelligent' attraction - it varies with my state of mind). Then we figure out how to engage her in some fashion that allows it to be escalated. Sometimes that works (it can get escalated into a date), but probably more often it does not (no mutual attraction or interest). So these men move on. Sometimes, we even become inured or disenchanted.
Psychologists often write that men appreciate direct conversation, while women are more indirect. So, if you want to ask a man like me out, be
direct. It's hard to do if that is not your style of communication, but it is what works. After all, men are stumbling around trying to figure out the sort of
indirect communication that works with women. And if a man tells you it doesn't hurt that he's rejected, baloney. He just doesn't yet recognize or admit it.
With all the difference in communication styles, its a wonder that the genus
**** sapien can propagate.