Question: I have a date this weekend with a girl I was set up with. It's basically a blind date, but with Facebook and Google, it was easy to look her up so I knew what I was getting myself into. I ended up digging further than I anticipated and I found some interesting articles about her on Google. Some were good (there was an article from her high school about how she was a star softball player), but some were bad (an article from her college's town newspaper about how she was arrested for drug possession). What is protocol around these things - can I bring these up to her and ask her about it? (Denver, CO)
Social Shrink: This is 2010 - everybody Googles people they are curious about. It shouldn't be a surprise to anyone if someone says they Googled you and found some embarrassing photos of you from your past. While the Googling may be standard procedure nowadays, it's the content of what you find that is tricky bringing up.
If it's your first date and the two of you haven't even formally introduced yourselves, it may not be a good idea to bring up such details on a first date. Get to know each other the good old fashioned way and let her tell you about herself. Go into it with no judgments or expectations (as hard as it may be since you'll naturally be curious), she deserves to let her share her life on her own terms, especially on the first date.
If you two hit it off and you decide that other dates can follow, that is when it may be a good time to bring up the not-so-good article you found. Once the two of you have established a rapport and it's clear you both like each other, jokingly admit that you Googled her before your first date. She shouldn't be surprised (and may have done the same for you), and she may see that as a sign that you were anxious to get to know more about her.
That should set you up nicely - her response: "So... what did you find?" Nonchalantly bring up some of the articles about her softball awards and then give her the opportunity to add anything else she may have thought could have popped up. Chances are, she may have already Googled herself to see what came up (come on, we Google ourselves as well) and knows about that article.
If she doesn't bring it up right away, don't force it out of her. Maybe you can help ease bringing it up by admitting something embarrassing from your past. Regardless, if you like her enough you can wait for her to clarify down the line. It's something that is (hopefully) in her past, something she's ashamed about and not a part of her life now. In the meantime, focus on the 'now' and enjoy the present time getting to know her. She knows she can't hide from it forever - cyberspace has a way of coming back to everyone whether we like it or not!