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Should I do overtime at work to be able wine and dine this chick?

From Jordan
This girl I'm seeing always wants me to take her out for meals and drinks and always just expects me to pay!

I don't want to look cheap or lose face as I know she's impressed with me not 'seeming' to care about how much stuff cost but she's bleeding me dry!  At this rate I'm going to have to do overtime just keep it up.
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Should I ask her to pay next time? If so, shall I say something before we go out or just drop it on her at the time?  ...Or shall I just do overtime to carry on paying and not risk losing her?

Reply from The Man Dem
Looks like you got yourself a gold digger there boy!  Any girl who ain't at least offering to pay for drinks after the first date is playing yo ass for a fool.  And overtime to fund dates??  Calm the fuck down!

Test the water on your next date to see if she is actually a gold digger by saying at the start of the date "I've forgot my wallet so only have the money in my pocket tonight".  This should show you her true colours.  No offer to pay means no interest in you without your money. If that's the case, get your money's worth that night and then move on to a more worthy girl for your long term relations.

~Dee
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