A Successful, Unintentional Pick-Up Line

I was at a bar after a comedy show in NYC. I was in a circle of 6 or 7 people, a few of which I knew well and a few that I had just met that night. I turned to the girl next to me, an auburn-haired girl in a striped t-shirt dress who I didn't know.

"You look so familiar to me. Is there a famous person people say you look like?"

"I get Karen Gillan, a lot. Do you know her? I think it's just because of the hair though."

To which I somewhat absentmindedly replied, "Hmmm... yeah... I can sort of see that. You're like a prettier Karen Gillan." And thus commenced a relationship that would last almost a year. 

Later that night a friend said to me that that was a great pick-up line.

But it wasn't a pick-up line. It was a genuine question followed by a genuine off-handed statement. She did remind me of someone. And I did think she looked like a prettier version of the person she suggested. 

I don't use pick-up lines. I'd be more uncomfortable having something scripted to say to someone than I would be just speaking off the cuff. But you can certainly use this structure as a pick-up line. I think it would work pretty well too. In a non-creepy manner you are able to suggest you're noticing her appearance in a positive way. And you get to favorably compare her to someone who is probably known to be attractive (as most female celebrities are). 

So, to reiterate, here's what it would look like:

You: You look very familiar to me. Is there a celebrity people say you resemble?

Her: Some people say I look like _____________.

You: Hmmm. Yeah, maybe. I can see that. Like a prettier version of ___________.

An alternative to this, if you're a likable person who can pull it off without coming off as a prick or a douchebag who is "negging" the woman, is to interrupt whoever she says with a less-than-attractive celebrity.

You: You look very familiar to me. Is there a celebrity people say you resemble?

Her: Some people say I look like Jennifer Lawr-

You: Anne Ramsey! Yup, Anne Ramsey... that's it. It just came to me.