Dear Annie: Six months ago, I met the girl of my dreams at a restaurant that I frequent several times a week. I was eating lunch there long before she started serving, but the first day I saw her, I began sitting in her section. The problem is, every time she comes by, my tongue gets frozen, my voice changes, the words don’t come out right or I say something stupid. She isn’t seeing the real me.
A few months ago, I asked her out. She turned me down, saying she is too busy to date and, besides, she doesn’t date customers. I was bummed out, but I still kept coming to the restaurant, and everything seemed OK. Every day, I like her more.
A couple of weeks ago, I couldn’t resist bringing her flowers and a card expressing my feelings for her. She wouldn’t accept the flowers and only reluctantly took the card. The next day, she told me I make her uncomfortable and should sit in someone else’s section. I was totally crushed. I don’t know what to do. I haven’t seen her for nearly two weeks, and I’m miserable. I want to respect her and will eat somewhere else for a few months so she has some space, but I don’t want to give up.
I’m a successful businessman, and I work hard to achieve what I want. What is the best way to win her heart? Does age matter? I’m 38, and she is still in college. I am not only physically attracted to her. I really want to get to know everything about her. At the very least, I’d like to be friends. Is it possible? – Tom
Dear Tommy: Probably not. You have turned into that creepy older guy who hits on the waitress and won’t take no for an answer. She has made it quite clear she is not interested, and any additional moves you make in her direction will only confirm her low opinion of you. She might even quit her job if you keep showing up and mooning over her. Find another place to eat, and leave the servers alone.