I’m a male, 30, married for five years, father of two children, and a cross-dresser. 

When my wife and I started dating, I’d stopped cross-dressing, thinking I was cured. I was wrong. I’ve been doing this from age 8, and I’m not sure if my parents ever suspected.

For the past two years I’ve been doing it in secret whenever alone. I’m not sure if my wife has any clue but I’m tired of not being honest with her.

I don’t want to lose my family; I want to seek professional help. Should I tell my wife my secret? Or should I continue with this inside of me hoping to see if it’ll go away?

- Confused

Do not treat this as a “dirty little secret;” rather, it’s a form of behaviour you’ve been drawn to over the years for various reasons, and you need to tell your wife about it. You don’t want her to discover it, in a moment of surprise that’ll upset both of you. 

Use some of your “alone” time to get more informed about cross-dressing as a practice, so that you’ll learn 1) you’re not alone; 2) many habitual, part-time cross-dressers are married and couples deal with it in a variety of ways; 3) wives can be supportive and understanding if it’s explained to them in a non-threatening, non-excluding manner. She should be told, for example, that most cross-dressers are heterosexual.

I advise you to do this research (literature and support groups for cross-dressers wives-of, can be found through the Internet), then, see a professional counsellor if still uncertain about how best to approach the subject with your wife.

The reason why one friend stopped talking to another was told to me in confidence. Should I reveal it to save their friendship?

- Between Two

Recipe for Ruined Relationships: Meddle in the middle, and lose both friends… even if they end up reconciling.

My grandmother had to give up her youngest child (the fifth) for adoption. A family member adopted her at age four, but an ongoing relationship wasn’t encouraged. 

Later, the adult child was involved in questionable activities. She moved to an apartment she couldn’t afford and has been calling my grandmother more frequently for money.

My grandmother’s 90, living on a fixed income in subsidized housing. She’s constantly listening to her “daughter’s” hard luck stories and sending money. She also calls my mother – but we question what she’s doing with her finances, and suggest she finds an affordable place. So she’ll ask my grandmother to call my mother for money.

I barely make enough money myself but I know people and agencies that can assist her. I sent this information to her, but she didn’t follow up.

I asked my mother when is the family going to end this enabling behaviour.

Should I work towards getting the family to just say “no?”

- Fed Up

Unless this aunt (that IS what she is, by birth) is harassing your grandmother, or you’re asked to be involved, you must otherwise back off. There’s serious family baggage here, and the siblings and your grandmother need to handle it their own way. 

However, if you were to make a real outreach to this woman, in person, and offer to help her connect with the agencies you mention - showing true interest in her well-being - the sense of her having caring family could be far more helpful than your making judgments.

I’m 48, my fiancé is 51, first marriage for both. 

I have a large family, and I’ve been there for all - the good aunt, the “go to sister” in financial emergencies, etc.

We’re having a small wedding party. My best friend (maid of honour) is hosting a bachelorette party. I’ve expected that a sister or sister-in-law would offer a shower – none did. My best friend wants to approach them.

Am I being too sensitive by saying not to, yet feeling so hurt?

- Disappointed

Let her approach them, and let her say – diplomatically – that she believes you need/want this family support. They may’ve thought you and future hubby already “have everything,” as is sometimes said of mature couples. She can explain that it’s the celebratory part of the shower you really want (I’m sure it is). 

If they resist, focus on your happiness at being a “new family” together.