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The worst one Tyler probably had was when he was on a "just friends" date with Clair to a nice Holiday Hotel, and unfortunately there was a Pikachu mascot that paraded the place, so everytime it went over to Tyler, he'd yelp and hide behind Clair. She knew of his fear so she wasn't upset, but he was greatly embarrassed through the whole time
Casey hasn't had a date yet lol
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