If I remember right, he bought me the first one on his own and surprised me with it our first Christmas together. We'd been dating about 7mo's by then. It was a heart shaped amethyst and his mom helped him pick it out for me. I think she had hinted to me that I was getting a ring because I was kind of expecting it.
This was the really good part: He gave me this huge box, like a big TV box and inside were all these other wrapped boxes that were jokes. Like he gave me mousetraps, an old distributor cap from his car, I think one was even spark plugs; just junk to make me get excited and unwrap it. Inside were little notes teasing me about what I was getting or little things we used to say to each other. And finally, at the bottom of the box was the ring. It was so much fun to unwrap that!
So even better than the present was the giving of it. He put a lot of thought and effort into it, especially for a 16 year old. So even if it hadn't been a ring it would have meant just as much to me. I think this is also what you're looking for- seeing him put a little effort and thought into something just for you. As you suspect though, it won't mean as much if you tell him to do it. I think you can hint and it will still be special if you don't tell him specifics. Just see how he interprets your hint that you need a romantic gesture from him. Then what he comes up with will be from his heart and what he wants to do for you. But it has to be a SUBTLE hint!!
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Thought for the day: Men are like fine wine. They start out as grapes, and it's up to the women to stomp the crap out of them until they turn into something acceptable to have dinner with.
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