Always. Not even a choice anymore, I don't get asked.
I will never forget this time I met someone on MSN that I went to grade school with. We were kinda thrilled that we suffered in the same school (Well, I suffered anyway, heh). So, we are talking about meeting up sometime and she keeps insisting she wants to bring her friends with. I keep trying to tell her that I would be a lot more comfortable meeting her alone the first time. It was a public place, so it wasn't like I was going to murder her or anything. Finally, she wears me down and I agree to meet her with her friends and we will go bowling. We meet at a mall, spend like 5 minutes saying hello and such and then she whisks me out to the car to meet her friends. They all seem nice and it's clear she is much more comfortable with them. The ride to the bowling alley is awkward and I listen to them talk.
When we get there, I ask to sit out the first game and watch. It's been forever since I bowled. After the one game, they decide they're tired of bowling and we head back to the mall. Right as we walk in, she tells me that she can't stay until 5 like she thought, and she will have to leave in like 20 or so minutes. Great, my ride won't be there to pick me up until 5..
At this point, I am following her around as she shops for clothes and asks one of her friends for advice. This is not my favorite sort of stuff to shop for and it was all a bit random. One of her friends sees my pain and he tells me he is sorry about all this. Nice guy. Finally, I figure she will sit down with me as we head to Barnes & Noble, as they have a cafe type area. To my unhappy surprise, she runs into a girl working there who is an ex of hers and she spends the last 15 or so minutes of her time chatting with her. I just sit down on the floor a little ways off and I struggle not to cry. She says goodbye and they all leave and I retreat to the bathroom to cry alone. It was just so depressing to make this effort to come out and meet someone and they barely notice you exist.