When I was doing online dating (eughhhh!!!), I would steer the conversation so that I could bring up a bar / restaurant / coffee house / play / event etc etc etc and just come out with, for example; "Hey, I've heared the food is awesome at Luigis! Wanna go with me Friday and see for ourselves?"
90% of the time I would ask this at the end of day 1.
If I got a "hmmm, I dunno" response or a "no" I'd move on (and let them know). Its a dating site, not a fcking chat room

dont waste my time and cash. People are different through IM and e-mail than they are in real life anyways. I wouldnt bother spending too long trying to build comfort and attraction online. Better to get him face to face and do it instead!
I'm a dude tho, no idea if this works both ways. Pretty much all a girl has to do is smile, look good and ask me to get a date, lol.