Dear Abby | 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.

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DEAR ABBY: I am in a relationship with a woman 25 years my junior. We talked at length about some of the issues we might encounter before we embarked on a relationship. We love each other completely. Her father, however, strongly disapproves based solely on our age difference. He has stated that he had no issues with me personally.

She recently told me that she isn’t happy and she wants us to spend some time apart. Neither of her two marriages worked out. She says I’m not the issue.

She wants to be with me, but her father would shun her — and me — if we were ever to be in the same room. He has actually said he’d walk out if I were present. She told me he was this way with her first marriage, which he did not approve of.

What do I do? I love her, but I can’t get her to see how much I love and care for her and her two boys. How much space should I give her to figure herself out?

— TORN UP IN PENNSYLVANIA

DEAR TORN UP: The woman 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.