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The shirt you linked to is lovely. You should wear that with some khakis and nice shoes...you'll be stunning.
Wordy t-shirts are fine for every day, but not for dates. I mean, most guys I know would be disappointed if their lady fair showed up in jeans and a t-shirt. Maybe you wouldn't, and kudos to you if you don't care, but clothes help make an impression.
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"With all its sham, drudgery, and broken dreams,
it is still a beautiful world.
Be cheerful. Strive to be happy."
-Desiderata
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