I think it's really difficult for anyone to be receptive to any strangers for any purpose on the train. It's just not where your 'train' (pardon my pun) of thought is at the time. Public transit also has this 'prolitariat' feel to it that somehow makes it seem even dirtier to explain to your friends that you met someone on the train.
As for picking up women on the train, the only time I've ever tried was when some drunk homeless guy was wrecking havoc for the general populace on the train after normal working hours (I think it was like 8 or so at night). The homeless guy approached this girl and started trying to talk to her in his broken speech. She looked thouroughly disguisted with him, so I started up a convo with the homeless guy to distract him until his stop at the end of the free fare zone downtown. Afterwards it seemed to be a nice lead in to a conversation with her, got a phone number! Seems to me it was made easy only due in part by a window of opportunity to talk to her without looking like some guy trolling for his next prey.
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