My wife and I were both raised fairly conservatively, so she never ended up getting her ears pierced and of course I didn't have mine done either.
Well, we're both in our early 30's now and about a year ago I caught her doing research into piercing shops. I asked what she was up to and she said she'd always wanted to get her ears pierced, but that she was too afraid to do it. I knew though that she wanted it because she loves jewelry. She said "maybe I'll do it if you do." I was like "OKAY!"
Well, she backed down a little bit out of her fear of needles over the next few months and for a while I thought maybe she'd never get them pierced. But last month was my birthday and as it was approaching she asked, "so what do you want for your birthday?" So I said, "the only thing I want is for us to both go get our ears pierced together."
I told her I had researched a local piercing shop that had very high reviews, and very competent staff. And SHE SAID YES!
I told my sister and she said she wanted to come along too and get her nose pierced. So we all met at the place and did it!
I was scared to death, but it really wasn't that bad. It's been about 4 weeks now and I haven't had any complications. I just got some basic stainless steel studs for now, but I am DYING to be able to put in some proper earrings.
I've come to realize that this is one of the body modifications that people can do that works well for boy mode and girl mode. There are stainless steel studs you can get that look very basic. Now that I have them pierced I notice that a lot of guys have both their ears done and there are lots of options for studs, I just hadn't noticed before as much.
Anyway, I highly recommend it. For my birthday a few days later my wife got me my first pair of pretty earrings. I can't wait to wear them! If you are worried about people giving you weird looks - don't. It's been great for me so far.