[Two Pronged] A cross-dressing husband seeks a chance to reply

• Andrew expresses regret over his broken promises to stop cross-dressing, which he believes contributed to his wife's diminishing love and eventual departure, while also feeling misunderstood about his identity.
• The column's response emphasizes that it was not the cross-dressing itself that caused the marriage to fail, but Andrew's repeated failures to communicate openly and honestly with his wife, leading to a breakdown of trust.

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Rappler’s People section runs an advice column by couple Jeremy Baer and clinical psychologist Dr. Margarita Holmes.

Jeremy has a master’s degree in law from Oxford University. A banker of 37 years who worked in three continents, he has been training with Dr. Holmes for the last 10 years as co-lecturer and, occasionally, as co-therapist, especially with clients whose financial concerns intrude into their daily lives.

Together, they have written two books: Love Triangles: Understanding the Macho-Mistress Mentality and Imported Love: Filipino-Foreign Liaisons.

Dear Dr Holmes and Mr Baer:

I refer to your column of Oct 10, 2026.

I do not intend to sue you for publishing the half-truths of my wife, but I insist on (the) right of reply. This column allows that, I presume?

I have every reason to believe my wife (or former wife, as she insists although divorce is yet to be legal in our country) wrote the letter you published the 10th of October, 2026.

All the details she mentions are accurate, although there are other facts she forgets to mention:

1. Yes, I used to cross dress and it is my eternal regret that instead of sharing this voluntarily with her, she discovered this on her own. I immediately promised never to do it again.
2. She said it explained many things that did not seem right in a marriage between two people who loved each other. I love her — and still do, despite the years we have been separated.
3. I gave her many books and research articles to read unequivocally stating that my being a cross dresser did not translate to being gay and/or being transgender. After a while she stopped reading them. I cannot understand such denial of logic.
4. How could she refuse such undisputed data? My wife is also an attorney, but working for a non profit. She has a good heart but no business sense. Her final decisions are guided by heart, not a hard core mind.
5. Each time she discovered I broke my promise never to cross dress again, I could feel her love for me diminish.
6. I will never forgive myself for this, but each time I failed, there was a very good reason that I did.
7. When she finally left me, I stopped cross dressing for the next few years in an effort to win her back.
8. She has always refused my attempts at reconciliation, so can you blame me for going back to cross dressing every now and then? I am not gay, I do not hate women, and I don’t think I am a woman trapped in a man’s body. I just enjoy doing so. It provides much needed relief from a job that is full of pressure.

Any thoughts?
– Andrew

Dear Andrew,

Thank you for your email. This column welcomes all responses of whatever nature, positive or negative. In this case, there is just one caveat – we will answer your letter without treating your wife as a party to this exchange since we have not verified any connection between you.

Your letter states that you regret that rather than hearing about it from you, your wife discovered your cross-dressing for herself. You also acknowledge that your broken promises diminished her love for you and eroded the trust between you. However, regarding the broken promises, you claim that there were ‘very good reasons’ for them, unfortunately without revealing what these were and thus forestalling any analysis of your reasoning.

It seems clear that despite your concealment of your cross-dressing, it was not the cross dressing per se, but the continuous breaches of promise that drove your wife from the marriage.

This was no doubt exacerbated by your decision to conceal the supposedly ‘very good reasons’ from her, since how was she to be expected to understand you if you consistently failed to explain yourself?

Perhaps it is also significant that you have done exactly the same in your letter to us — claimed that there were ‘very good reasons’ without any further explanation. How are we then expected to evaluate this situation, much less your wife?

Your refusal to explain yourself, together with your efforts to deflect by deluging your wife with information to prove that cross-dressing did not mean you were gay or trans, suggesting that reason alone should convince her, are thus what drove her away and you seem to make it clear that you never altered these tactics, despite claiming you wanted to win her back.

So, to answer your question, no one can blame you for going back to cross-dressing now that you have alienated the only person whose opinion you actually wanted. As for further thoughts, perhaps it is time to recognize that your marriage is over for good, regardless of the law.

Further efforts to win her back will simply confirm what she already believes, namely that your promises are hollow.

All the best
– JAF Baer

Dear Andrew,

Thank you very much for your letter. There are two points Mr Baer brings up in his answer above that I would like to expound on.

First, it was not your cross dressing per se that caused your wife to leave you. If it were, she would have left you the first time she discovered it… or the second… or, at the very most, perhaps the third or fourth. It was how you promised repeatedly that you would stop doing so and never did.

How exhausting that must have been for her! And yet… AND yet… I see no attempt on your part to understand how she must be feeling. Instead, I read rationalization after rationalization about why you behaved the way you did, and why you have gone back to cross dressing. And even then, you rationalize why you went back and manage to blame her for it!

Besides, for a lawyer who seems to place logic above all else, is it not ironic that you “immediately promised” never to do it again. This belies your statement that you find nothing wrong with cross dressing. I feel it is only when you finally reach point #8, your last point, that you seem to give the actual reasons you cross dress: “I just enjoy doing so. It provides much needed relief from a job that is full of pressure.”

Why in God’s name did you not share this with her? Why did you not open your heart to her, trusting her to believe you (or, at the very least, hoping she would believe you)?

There seems every reason to think she would have. After all, she believed your promise to stop cross dressing (even if you felt there was nothing wrong with it, as all the research articles and books you insisted she read confirmed).

I realize that, with the quick razor-sharp mind you pride yourself on having, you will accuse me of merely projecting my own feelings when I share another reason for your wife’s refusal to believe you. But clinical experience says otherwise.

Many — though admittedly not all — people who pride themselves on, and convince themselves that, their intellect is what makes them who they are; that it is their formidable mind that makes them not just admirable, but also lovable.

Not so. I have yet to hear a wife say the major reason she loved her partner was their IQ. Many — and admittedly not all — women who love their partner do so for inner qualities that usually cannot be measured by simple metrics. Most women love their partners basically for how their partners make them feel: cherished but also safe.

I can’t help feeling it was your behavior and your arrogance, both during your marriage and after it ended, that was the nail that finally ended your marriage.

Here’s hoping you find the courage to discover some truths — and not mere data — about yourself

– MG Holmes

– Rappler.com

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