Hey Doc,

I’m 33 years young. Every night I listen to seven chapters of “The System.” I also listen faithfully to your radio show. You stated on the show that incoming group dates should be accepted, because anything incoming trumps the “no group dates” rule in your book. Does the same hold for incoming trip requests? I’m asking because I am seeing Kelly, who is 29 years young. We’re eight dates in (although she’s not hinting that she wants me to be the boyfriend yet) and she invited me on two upcoming trips.

The first trip is a four-day cruise (her friend dropped out so she invited me to take the spot before inviting one of her other friends), and the second is a four-day trip down in San Diego. She would be paying her half of the expenses and we’d be sharing a room in both cases.

I had thought that these invitations might be hints that she wanted me to be her boyfriend. But she said that this wasn’t her taking the next step with me (“We’re still building towards a relationship,” was the way she put it), but that she thought it would be fun to go with me on the trips. I’m actually out of the state for work on both occasions, so I expressed my regrets that I wouldn’t be able to go and countered with a date request for each, following “The System” rules.

However, assuming I wasn’t stuck on work assignments, should I have accepted her incoming invitations for these overnight trips? I had thought it was a pretty clear rule in your book to not do that (and I’d be uncomfortable sharing a room with Kelly before we became boyfriend/girlfriend), but thought I would ask you if the incoming date rule trumped the no trips rule.

This situation seems a little weird to me, so I’m treating it as a minor Red Flag since Kelly and I aren’t boyfriend/girlfriend yet. But I’m also flattered that she is comfortable enough with me to invite me along on these excursions.

Wes - who likes to keep to the rules