The naysayers are probably for the most part correct, especially that "creepy guy with personal data" part.

OTOH 27 years ago I was teaching classes in Wang word processing at The Hunger Project in San Francisco and a woman in one class was truly terrible at it and bristled and recoiled at every suggestion I offered, making for some very interesting in-class drama.

After a week of classes, I offered to meet her in a local cafe - a block away - on an off day, whereupon she said yes (It was NOT a "date") and I brought a user's manual and subsequently passed 4-5 hours helping her "get it".  She did.  About a month after she had finished the class I ran into her somewhere else.  We had some more coffee, and I asked her out to a movie, and, well, we celebrated our 25th anniversary in March 2011.

It can be done.  But that built-in creep factor should be kept in mind.