I've been curious about this situation:

There's a girl at work I'm interested in but never really get to talk to. We work in different areas and for the 1/2 hour a day we do have the chance to interact I never really have anything of interest to say so I keep tight lipped. I say hello when our eyes meet and she actually opens me with opinion questions every now and then. When we do talk she looks at me very intently and I make her laugh. Most of the time though we just pass each other by, sometimes not speaking for days on end.

My co-worker on the other hand approaches her and other girls all the time but he uses the worst, cheesiest, pun-filled jokes. The girls laugh but usually it just seems like they are only being polite. One time he even went on about his long underwear. He's not interested in these girls but he does get out there. I stand quiet and look the fool as he opens his mouth and appears foolish.
And the funny thing is he comes to me for dating advice and I'm 14 years his junior.

Now my question is: Is approaching often with bad jokes better than rarely approaching at all but having good material?

I'm really thinking the answer is a conditional yes. All I have learned says just get out there and start the conversation and build from there.

Thanks for any response guys.