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by Abigail Van Buren

Cross-Dressing Best Friend Wants to Go out as a Couple

DEAR ABBY: My best friend and I are both male and 25. We've been friends since third grade. We were apart for four years of college and two years after because we were employed in different states. He has now been transferred and lives and works a few miles from where I do. We see each other frequently and often double date.

He recently shared a secret after pledging me to secrecy. He's a cross-dresser. He says he's not gay, and I believe him. He has pictures he had taken professionally in which he is completely feminine and even beautiful. He says he has been dressing up since the age of 12.

Abby, he wants to go out in public with me as a couple. Even though he is small and would easily pass, I'm just not into it. And what explanation would I give to my girlfriend? He says if I won't, I'm not a true friend; I say he isn't. Is there any way to resolve this? -- TESTED IN TAMPA

DEAR TESTED: There is a way, provided your friend is open to it. How about you and he and your girlfriend going out together? Of course, your girlfriend would have to know the truth, and your friend would have to be OK with her knowing. This way if you were seen with "another woman," it wouldn't cause conflict with the woman you're dating. That said, you should not do anything you are uncomfortable with, so think carefully before deciding.

Read more in: Friends & Neighbors | Sex & Gender | Love & Dating