Raw oysters are actually sometimes easier to eat than smoked/canned/cooked, because you just slurp back the raw ones! No chewing, plus some tasty vinaigrette or hot sauce all over. If you go to a restaurant and get them (go with an oyster-lover, or just someone who's oyster-curious so you can keep each other committed) you will get the benefit of not having to shuck the oysters yourself (usually a oh-my-god-Im-going-to-lose-all-my-fingers experience if you are doing it for the first time with a knife), some properly prepared sauces, and usually the advice or guidance of the wait staff (they're used to it- I used to work at a restaurant that served them, I would say 60-80% of patrons had never tried them before). If you do try fresh oysters, and don't care about eating them raw, skip the shucking and throw them on the BBQ. They pop open, so you don't even have to worry about when they're done or if you're over cooking them. I usually put a herb compound butter slice on top, then crumble some bacon, maybe toasted pine nuts as a treat. My mom does plain garlic butter, my boyfriend does finely chopped habenero and garlic. You could do a smorgasbord of different kinds of toppings to share with a friend, so at least you'll have fun even if you don't like it too much at first!
Alternatively, buy smoked oysters, wrap them with semi-cooked bacon, throw in the oven to heat and crisp, then eat. You can also make a seafood pate of shrimp, scallops, oysters, clams etc in a food processor, but that only works well (and tastes awesome) if you like seafood in general.
My strategy for trying to get a taste for new foods, is to try to make it not that big of a deal. I won't go out and buy a pound, then fret about having it in the fridge and needing to use it up before it goes bad. I will casually try and eat things that I know I don't like at parties or restaurants because I know that based exclusively on manners, I'm going to have to eat at least half of it. I used to hate olives- so I would try and casually just no-big-deal pop them in my mouth at parties. Besides a few gags and close-calls (note- don't employ this strategy on dates or work parties, don't want any surprises), it seems to work pretty well. Just try it a few times, in a few different ways, and then you can try and work up to including them in your diet.
I used to have this awesome customer that would come into my store, a really hilarious but strict mom of two boys who was a foodie, and she always said you can never say you don't like something until you've tried it 42 different ways. Unless you've tried it in 42 preparations and disliked it every time, you can't say you don't like a food. Her boys were so adorable, they would try things and then tell you "I don't like this particular preparation, but I look forward to trying it in a different way sometime". I thought this is such a great attitude, so I always keep this in mind when I'm trying new foods. Takes the pressure off of liking it every single time- maybe we'll hear back on how you life oysters after your 42nd time trying them!