Lemme try!
“I’m going to the ghetto to buy some crack. One of the dealers gives me a good price, want to join me?”
Like that?
Yes. Perfect for dating a crack ho.
I’m speaking from experience, giving the advice I wish someone had given me. I wasn’t cowardly: when I had a crush on a girl, I invariably let her know and asked her out. And I was invariably rejected, because I put so much weight on it, because I freaked myself out about it so much that it completely weirded the girl out. And I never ever ever asked unless I was crushing, because I had this ridiculously romantic idea of what love should be like.
If I’d gotten practice in low-stakes circumstances–if I’d learned what worked and what didn’t work when I had the safety net of not really giving a shit–I think I’d have been much better off.
It’s not that he shouldn’t ever ask anyone out that he’s interested in: it’s that if he’s posting a thread on a messageboard about it, I’d put the chances close to 100% that he’s gonna freak out enough that he’ll get rejected in this case, and unless he can shrug and move on after the rejection, this isn’t a good way to practice the skills involved.
Is she cool with his 3 dates a month? 
Hey, he’s gotta do what he’s gotta do.
(Incidentally, it was three dates a month because he told me about the regimen about four years ago, and I can’t be arsed to remember exactly how many it was, whether it was one or three or four or six, so I just made up a number, that’s why).
Well, I agree if he can’t shrug it off then he shouldn’t ask. But you’ll never learn how to just shrug it off unless you jump in headlong. Right? This is how I learned. I’ve gotten my heart bruised on a number of occasions asking someone out and getting turned down, and I’m sure I’ve bruised my fair share of hearts as well. But the experience makes us tougher and more able to handle those situations. At least in my experience. It hurts, you dwell for a bit, then you move on and get over it. However, I’ve never asked someone out who I wasn’t interested in, and I would never want to be asked out by someone who wasn’t genuinely interested.
Disagree with 99% of the advice given so far.
Ask your original-post question of she whom you have in mind. The thoughtful intellectual replies will make for good conversation and favorable interaction in their own right, quite aside from the likelihood that discussing exactly how one would go about doing such a thing accomplishes everything that actually doing the asking would accomplish, except in a much more pleasant fashion.
What do you mean by freak out? I’m not taking it personally, just want to know.
Last time I did it, words came out fine on the phone even if nervousness must have come through. The time before that, it was in person and though I averted my eyes after she started giving me the “I’m really busy”, I don’t think I freaked out.
Lead them on for what? It’s just a date. Are you one of these people that would only consider asking someone out that you would consider marrying?
Most people realize a date is a date. While it may possibly someday later might lead to something more serious, most people take it for what it is. A Date.
Fair enough; I’m almost certainly projecting. All the same, I’ll give you the advice I wish someone had given me: dating is, or should be, pretty low-stakes. If you only pursue dates in high-stakes situations (i.e., with folks you’ve decided you’d like to have a serious relationship with), you’ll screw it up.
If that advice doesn’t apply to you, my apologies!
There was so much advice on the page that I had to just scan it after a while. But, did I miss somebody else saying “Knock off this movie in 30 minutes” nonsense? Dude. That is scary.
hh
…while declawing a circumcised cat offered by Monty Hall.
Anything come of this?
Last Wednesday, I hear in the morning that I have access to free hockey tickets. This reminds me: MK likes hockey! So when MK and I are waiting for class to start, I ask her if she’d like to go Sunday. She says she won’t be in town but she’d have liked to go. I didn’t detect awkwardness like the last time I was turned down.
Today, I phone 4 women I’d been meaning to ask out.
P : She answered that her job had her working during those days.
MK (again): She said yes. Her voice seemed enthusiastic. She told me to call her back on Tuesday to know how far along she was in her study (we’re both law students, reading week is very aptly named). This sounds very much like her leaving herself a door opened to later refuse, but the last time I asked her out she had no problems telling me plainly she was going to be out of town on the day I had planned. I’ll find out on Tuesday.
I: Said she was going on some reading week vacation next week.
C: She was the one who prompted this thread. I had little anxiety asking the other women out because I thought of it mainly a way to desensitise myself and get my nerves under control by doing it several times in a row so I could half-decently ask C out. Last time a woman attracted me this much was 2 years ago.
I asked her out for next weekend but she wasn’t going to be in town. I thought that was an excuse to let me down easy but she suggested we do it the weekend after that. She seemed to be put in a good mood by the request.
So, thanks for the input. Look forward to an equally dread-filled post asking about the next step I should have learned a decade ago.
Congrats! I was about to ask the guy who I’m interested in out and he beat me to it, which is a great feeling by the way. 
A word of advice, when the date is over, I think it’s good to say something like “So when would you like to do this again” or something to that effect, assuming the date went well. I didn’t even think about it until I was in my car after having dinner this past weekend, but I wish one of us had said “Let’s do this again sometime.”