I'd do the multiple "middle distance" runs (w/ multiple pops).  

Then again, I haven't done an overnight (unless you count my stints in Thailand and Angeles City).

I've never been a big fan of overnights... you're essentially paying the girl to sleep for part of your time.

If it weere me, I'd go for the two four hour dates.

I have done numerous overniters with only one girl and you really must click. I have also spent a weekeend and traveled with her. The one thing i know that helped me was you should discuss what you want and expect out of her. The main thing is you really need to get along good otherwise it will be torcher.

I'm not a big fan of paying to sleep. I'd rather have two 4-hour sessions.

Two 3 hour dates.  I've done overnights but only because it was a great deal and we clicked.  Overnights can be rough especially if you have never met.

In the spirit of the other responses - Unless you've established yourself to a point with someone for the overnighter, go with the dinner date and have a blast.  Then do another later on.

Ironic you did not mention doing doubles...

I had an overnighter with someone I had no earlier experience with - thought with the little brain on that one.  It was fun while we were awake but the pay to sleep thing never crosses your mind till its too late.

BTW - who will be the luck "present" for your birthday?

I would never do an overnight with someone I had not seen before! Invitation for disappointment.

Re: Dilemma - what would you do?

Thanks for the feedback guys. Think I'll go the two dates route.