Etiquette Question: Celebrity Lookalike

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Telling someone they resemble someone else is often a tricky situation. I've heard people who were told they look like a celebrity complain that they don't think that celebrity is particularly good-looking, hence even if the resemblance wasn't meant as an insult, it was taken as such. Last week I bit my tongue for as long as I could before telling a new friend that he looked just like Stephen Colbert (and then of course he said, "He's ten years older than me!") and I had to say "But he's very good-looking!" and then sounded like a creep. And then a few days later I was dying to tell someone else that she looks like a prettier version of Natalie Portman but she had just told me a story earlier about an acquaintance of hers who often tells her that she's pretty in a condescending way, so I kept it to myself.

Monday night I was watching RuPaul's Drag Race when I realized that Raja, in the patriotic challenge, was reminding me the hell out of someone I know:

Now, granted, as Shangela pointed out, Raja's eye makeup was the teensiest bit Paris-Hilton-wonky in the challenge, but other than that, I could only consider it a compliment to look like Raja. I mean, those legs! That hair! Plus, anyone who watches the show knows that Raja's also the funniest, meanest girl on the show with the best fashion sense and runway walk. I would love to be compared to Raja (but I'm too short and roundy.)

But then again, maybe it's not a compliment to tell a female that she looks like a man with his privates tucked away dressed up like a woman. Even if it is Raja. I don't know. Etiquette is such a bitch.