I am planning on doing a DW Sunday with a few others.
Your girlfriend doesn't really have to pick you up.
The trolley stops every quarter mile and can take us back upwind for a buck fifty. Or, we can drop one vehicle at the Undertow and then go North.

Should be a great DW day.
Keep in touch on here and we will figure it out as the time nears and give directions, etc.
Last time (a couple weekends ago) we went from John's Pass to the Undertow and it was great. We took lunch/drink break after the DW and then rode in front of the 'Tow for a couple more hours after the break.