If you are not literally rolling in hundred dollar bills like a manic Jewish rock star, then you have probably felt the tug on your wallet during a date.  The tug is probably not coming from a homeless person trying to steal from you. What I am speaking of is more of a metaphorical force pushing against your modest budget.  There are several obvious alternatives to a fancy restaurant or bar.  Picnics, the beach (if you are near water), bike riding, or museum-visiting are all horrible options and I would agree to none of them.  On top of that, if you take a date bike riding through your neighborhood, s/he may have questions like: Does this person own a car?  Or: Why are we weaving through a mobile park?  Even on a creative cheap date, the other person might suspect something.

This is why you need to become a millionaire.  Might I suggest the lottery?  I might.  If I did, that would be a terrible suggestion.  Should you turn to a life of crime?  Perhaps.  Again, not the most advisable course of action.  If you live in West Texas, it is highly likely that, sometime in your life, you will come across a satchel with two million dollars in it after a drug deal gone awry.  In order to keep the money, though, you must escape the clever man hired to kill you.  Or you could rent No Country for Old Men from a convenient Redbox.

Personally, I try to schedule my dates around the times that I would have the most money (for example, after payday).  That way, there is less pressure on you if your date orders a whole lobster or wine from a golden bottle.  Also, if you do not have paydays on a regular basis, you either have no job, or you have a really good job.  In either case, my advice will not help you at all.