Should I text her while on vacation?

If youve only been on a couple of dates with this woman, make sure that before she leaves (i.e., the last time you see her in person before her trip) that you let her know you want her to have an awesome trip. Now, regardless of what your status is, wait two to three days to text her when she is on her trip.

When should I go on a trip with my boyfriend?

If three months is the benchmark for your first couples holiday, two to three days is the best starting point for your break. James always recommends starting your travels with a weekend away before even considering anything longer. That way youll have a practice run and will be sure you are ready to commit to more.