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- 1 (2021-02-10 (水) 01:31:13)

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Hey, Kiki! It does sound like it’s about time for you and your beau to go on a vacation. My advice to you is to wait and let him bring up the topic of going on a vacation for several reasons:

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.