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Maybe he's shy, too, and doesn't like being asked for directions.
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Most guys that age turn shy pretty quickly when dealing with an attractive female.
As for my original post, being independent and dealing with people outside of your comfort zone is not "growing away" from Grace. It's growing, period. Keep in mind I'm in the same boat, and when I was younger (Jebus, now I feel like an old fart) I would never approach somebody if I were lost. I would just wander around until I wasn't lost (which I did, alot, lousy sense of direction). To this day, I would walk out if I didn't get served at a restaurant. What I do now though, is put a penny on the table.
I think your Denny's experience was entirely not about anything you presented as a person. You were there alone, which means the waitress (who is legally paid all of $2.13 an hour) assumed there would be a much smaller tip than larger groups. And Denny's has never been known for its sterling management or customer service. Your waitress probably went home that night and bitched about the single woman who took up 10 seconds of her time while she was trying to milk a famiily of five for a lousy $3 tip. Having worked in restaurants, and also having been ignored several times when I've dined alone, I can tell you this is how some waitstaff operate. I also know that if you piss them off, they will spit in your food.
That's why some of us get educations so we can make more than $2.13 an hour.