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I'm Afraid of My Kid's Fears

My son is a tough kid in many ways. He climbs to the top of the monkey bars and hangs fearlessly. He handles emotional scuffles with ease. He loves to wrestle and usually I'm the one who ends up crying over a bruised arm or bump on the nose.
But in many other ways, he's not so tough. He's afraid to ride a two-wheeler. He often cries at swimming lessons. He doesn't want to go on roller coasters, Ferris wheels or the teacups at amusement parks. (Sigh, he even still sits on the boat seat on the carousel, afraid of the animals that go up and down.)
And last week when I took him to a pirate-themed mini-golf course, he refused to go in because of the "scary guys" (i.e., goofy plastic pirates with lopsided grins on their faces and speakers in their mouths making it seem like they were shouting "Ahoy! We're after ye gold" and other pirate lingo). When I finally convinced him that I wouldn't let any harm come to him during miniature golf, and we made it to the ninth hole without any scary pirate encounters, we came upon a portion of the course that was behind a curtain: glow-in-the-dark mini-golf. It was so cool! I thought the colors were magnificent. I felt like I'd died and gone back to the black-lit velvet-postered '70s. I turned to Kayne and said, "Look at the white on your shirt, how cool it ..." Where was he? Outside the curtain, chewing on his lip, trying not to cry. He's afraid of the dark.
Oh, honey.
The thing is, I understand. I'm by no means fearless. I was afraid of the water until I was 40. I'm afraid to learn how to drive a motorcycle. I'm afraid when it is pitch black.
I know what it's like to dig my heels in and refuse to run into the arms of the bogeyman. But that's exactly why I want to help my son get over his fears. I don't want him to miss out on all the things I missed out on as a kid because I was afraid. Pool parties were miserable. I couldn't bike with my friends. Snowmobiling was out of the question.
I want him to experience life to the fullest. But what's the best way to get him to face his fears? Do I force him into situations where he's afraid in the hopes that he'll overcome the fear and then feel stronger? But what if he just gets more afraid, and his fears grow worse because he wasn't ready to face things on his own? What's the best way to scare up some courage in my little guy?
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