As a scuba instructor, I've seen people certified before they went through all the OW dives (in my mind this was true, they still did all the training). In common parlance, it's the carpenter, not the tools that matter. If your boyfriend takes to it very quickly, hooray! However, if he doesn't, it will take more time and practice...either way, just go for it and take it one day at a time. My suggestion would be for him to do the book and the pool in Boston, then you guys shoot down to Bahamas or something like that for Open Water...Bonaire is going to be too pricey...actually, Puerto Rico (South Shore) would be great, and its a fun trip. Dominican Republic is also very reasonable...the bottom lines are 2: First, make sure he's doing this for him (he actually wants to dive) and not for you (including that he doesn't feel cool if you dive and he doesn't). I see the reverse more often (the overbearing boyfriend or husband 'forcing' (figuratively) the girlfriend or wife to dive), and it really never works. Second, if he takes to it quickly, that's great, but still take it slow. If not, and he wants to get it, he will, and either way you'll be diving together in no time. Good luck!