Why are you just repeating what EVERYONE ELSE is saying?
Really? I see people telling him to do it over the phone, to not do it on a train, to do it in person, that the train is fine, to stalk her and show up with flowers, to make sure she understands it's a date, ways to communicate, things to keep in mind, blah de blah blah blah.
Caesar seems about the only person to really share my sentiment.
If that's all your going to do, DON'T FARKING POST.
Seriously, I agree with you somewhat, but if the only added thing is 'and you suck', it doesn't need to be said.
I don't see anyone else saying the only thing that matters is that he be proactive and take what he wants. I see a lot of well intentioned advice by people who seem to think the how of something that's never going to happen matters. It doesn't. He's had more than a year to do something about this girl he says he likes and he's failed to take any action at all.
Maybe it's because he has a crippling fear of rejection. Maybe it's because he's got completely unrealistic expectations. Maybe it's because he thinks he'll never live up to her standards. And
maybe, and I haven't seen anyone else say this,
it's because he doesn't want it enough to overcome whatever else is getting in the way.
Am I telling him "you suck?" No. I'm saying that he'd better figure out what his motivations are, and that there's no reason to keep fooling himself if he doesn't care enough to make it happen.