- If you bring up the vacation, and he ends up paying for it (which is likely), you may find yourself feeling guilty about making suggestions regarding hotels, etc. since it’s “his money”. If HE brings up the vacation, it’s his idea and he’d probably love your input. You never want to come across as too pushy or too eager to plan things–especially not on the man’s dime.

- If you bring up the subject of the vacation, he may very well think of the vacation as “your idea” and not be very engaged with all the logistics that go into planning a vacation. You want him to play an active role in helping you figure out flights, hotels, activities, etc. and not feel like he’s being wrangled into a faux honeymoon.

- It feels better to be asked.

Good luck on your decision! Go on a vacation with your girl friends (in a real-live plane even!) while he slaves away at work. That may even give him more incentive to actually take you somewhere.
.-= Kaneisha´s last blog ..Letter to a Fabulous and Confused Woman =-.

I think it’s about time my boyfriend and I went on a vacation together… is it okay for me to propose this idea to him?

A little background information on my boyfriend and I — we have known eachother for a year and a half (we met through work), and we have been together for 5 months. He is a 34-year old lawyer and I am a 20-year old student (I work full-time as well), so there is a disperitiy in age and finance. He has a big trial coming up in May, and I was going to suggest that after his trial we could spend a long weekend somewhere. He does not fly, so it would just be somewhere we could drive to.

I am just not sure if it’s appropriate for me to be the one to propose the idea — and also, I don’t know how we should take care of the finances on the trip. He always refuses my offer to pay for ANYTHING when we are together, but I don’t want him to have to pay for an entire vacation (especially if it was my idea).

Your advice would be greatly appreciated. I love your site by the way!