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Did you complete the date requirment ? I am doing it a 2nd time in another saved game and that is what u have to  do is to  have a succesfull date 3 times.  Not just a date.  She has to like it, not be looking at her watch. 

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Gwen will not work, so you have to charm Jessica, Madison or Veronica.  These are in my call list.  Will require some play time doing this currently in one of my save points. 

No I mean I can't have a date in the bar because I can't unlock the club upgrade

You have to buy the bar first from Jessica's office. Then you can buy the club upgrade