Dear Dr. Date,
I’m a 24-year-old male and experienced enough to understand how relationships work. My parents divorced in 1992, and my first serious crush when I was 16 (she was 16 also) fell to the odds of teen pregnancy with another man. She wasn’t the first. I’ve managed to maintain friendships with these girls, but they’re now married.
I’m not embarrassed to say that I haven’t really dated before. The growth of my self-esteem has been stunted because of past experiences, and up until now, I’ve been perfectly fine with staying home on a weekend.
Four months ago, I realized a girl I’ve known for eight years has been living across the street from me. We graduated from the same high school and she’s always home on evenings and weekends. It appears she doesn’t have a boyfriend (lucky me) and it’s been six years since I talked to her. It really feels awkward trying to start up a friendship right now. I know she’s not seeing anybody, I just have to find out how to get her to notice me. I’m a really nice guy and looking for something more involved this time. I know I’m finally ready.
I have been waiting a really long time for something like this. She’s really cute and shy.
Can you help out with ideas to get her to notice me without scaring her? It’d be bad to hurt someone’s feelings you really care about who lives next door and then go on living a normal life of embarrassment.
— N

I like that you, perhaps inadvertently, equated a life of embarrassment with a normal life. This should give you a clue to the answer for which you seek. Everyone experiences those flushing twinges of embarrassment. Just the other day I shuddered for no reason at something embarrassing I said in front of my entire sixth grade class. The memory was vivid, but, like a buzzing fly, it was easily swooshed away by thoughts of all the great things that have come to me in my life.
You can’t let embarrassment pin you down. Trust that this old friend from next door is shy and make the first, charming move. You can probably time it so that you can “coincidentally” be walking home at the same time as her. If walking doesn’t work for you, try drinking coffee or shopping at the corner store while she does.
Shy people are very perceptive, so be completely honest. Start with the obvious opening line and smile and laugh your way from there. Shy people also like to be listened to, but they don’t like to be forced to talk, either. She may be attracted to the same things in you that you find attractive in her. Keep it simple at first and don’t violate her private space and world. A nice, honest smile and “Hi,” is a great way to get someone to notice you.