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 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.

Dear Abby: I am in a relationship with a woman 25 years my junior. We talked at length about some of the you love may be twice divorced, but she isn’t free. She is firmly under her father’s thumb. The age difference is the least of your worries.

Regardless of your feelings for her, because she says she is no longer happy with you, it’s time to make a U-turn. And when you do, suggest that if she wants to have a future with anyone, it will happen sooner if she starts talking with a licensed therapist about her relationship with dear old Dad. She will never have a life of her own while he’s running it.