Help my friend ask a girl out.

I have a friend who’s very shy. His name is Jurgen. He’s 27 and he lives near Paris. He likes a girl named Alice that he spotted at his old job. She’s a slim malagasy girl of 5ft5" with black eyes, short dark hair, full lips, and beautiful matte colored skin (his words. I have never seen her).

He says he does not have the courage to ask her out. They haven’t talked so he doesn’t know much about her. When asked why he doesn’t feel equal to the task, he claims that it too much of a risk because the probability of them being compatible is small.

Now, as his friend, I have tried many times to give him what I am certain is good advice. However, Jurgen is a bit muleheaded and has totally ignored my advice so far. I figured maybe if enough people talked to him, he would listen.

So, dopers, what advice do you have for Jurgen? I have given him this thread’s URL so he will be reading you all.

Here’s the crux. Sure, there is a risk of their not being compatible. But it’s clear that they don’t have any sort of relationship at the moment, so what does he have to lose by taking the chance? If she says no, she’s still the girl he sees but doesn’t talk to, but if she says yes, Victory! It’s a scenario with a chance for a huge reward, and a chance for things to remain as they are. But nothing will get worse.

I’d ask him this: what is the problem if she says no?

The problem is that the whole fantasy relationship he’s built up in his head will be obliterated. I had a friend in college who was like this. He would fixate on a certain girl and spend weeks talking about how perfect she was and how great it would be once they were together. Only after he was totally emotionally invested would he finally ask her out. Then if she happened to say no, he had to deal with that rejection (which, hey, that hurts no matter who you are) plus getting “dumped” from this intense imaginary relationship.

The local lottery has a slogan they put on all the billboards: “If you don’t play, you can’t win.”

Ask the girl out. Find something very neutral and public, in case you’re afraid you don’t have enough in common: lunch at a sidewalk cafe, an art festival…

If he does not ask her out, he will carry the regrets over not asking her for the rest of his life. It’s not worth it. At least if she rejects him, he can be angry and then get over it. Regret is eternal.

(“Malagasy”. Now there’s a group I don’t think I’ve ever seen around here (Toronto). With my luck, tomorrow the local paper will have a huge expose on the new Malagasy community centre, and I’ll learn that they’ve been living here since 1908 or something, but as of right now, I believe that I have never heard or seen a Malagasy person.)

Oh, and a nitpick: “matte” is a texture, not a colour. It means “not smooth and shiny”.

They’ve never talked to each other? Can he ask a mutual acquaintance to introduce them? Nothing big, but just stop by for a visit and say hello to a few co-workers. Maybe have a 2 minute conversation about where she likes to have lunch. Later decide to visit said lunch spot, and ask if she’d join him.

Just do it. In my experience, despite your fear, nothing bad every actually happens from aproaching women. Women want compliments. If you smile, and are polite, the worst thing that will happen is she will smile back, thank you and say she’s not interested. She may even have a friend she can introduce you to. If you’re lucky, you get a date. Just be nice, and maybe don’t mention that you’ve been watching her for a long time.

The simplest way to ask a girl out: Say you just won a $50 in the Lotto and think it’s bad luck not to spend it all the first night, so you need a drinking buddy.