Since TransVitae.com launched a little over a year ago, we have received countless questions about transgender dating. From navigating first dates to tackling relationship challenges, it’s clear that this is a topic our readers care deeply about. To help answer these important questions, we are excited to introduce our very own advice column: Ask Ana.
Meet Ana Marie Stelle, our newest contributor and the voice behind Ask Ana. Ana is a 45-year-old transgender woman who has spent the majority of her adult life dating openly and proudly as a trans woman. She has experienced the highs and lows of dating and relationships firsthand and is here to provide thoughtful, compassionate, and honest advice to those who seek guidance in the world of transgender dating. Whether you’re transgender yourself, a partner, or an ally looking for insight, Ana is here to help.
This Week’s Question:
Dear Ana: I’ve been dating transgender women for a few years now, and I genuinely care for and respect them. However, I’ve always been hesitant to share this part of my life with my friends. My last relationship ended because my girlfriend asked why I never told my friends about her. I couldn’t give her a good answer. I never meant to make her feel like a secret, but I guess that’s how it came across. Am I wrong for keeping this private? I don’t feel ashamed, but I also don’t know if it’s anyone else’s business.
– Jerry C.
Dear Jerry: The first red flag that jumps out to me in your letter is the word “secret.” The moment a person you care about starts feeling like they’re being hidden away, there’s a problem—one that has less to do with privacy and more to do with dignity and respect.
Let’s unpack this. You say you’re not ashamed of dating transgender women, and I want to believe you. But ask yourself—if there’s no shame, what exactly is holding you back from being open about it? Privacy is one thing, but secrecy is another. When someone you’re dating begins to feel like a secret, they start questioning whether you value them or if their identity is something you’re afraid to be associated with. That’s not just hurtful; it’s dehumanizing.
Why This Matters to Your Partners
Transgender women face enough challenges in the dating world without also wondering if they’re being hidden away out of fear of judgment. For many of us, visibility isn’t just about affirmation—it’s about safety, validation, and being treated with the respect any partner deserves. If your ex asked you why she was kept out of your social life and you had no real answer, it’s because deep down, you know this wasn’t just about privacy. It was about avoidance.
Ask yourself: Would you hesitate to introduce a cisgender girlfriend to your friends? If the answer is no, then it’s time to reflect on why that distinction exists in your mind.
Why It’s Important for You to Be Honest
It’s great that you care about and respect the transgender women you date, but being an ally in private isn’t enough. If you genuinely believe in their worth and dignity, that support should be visible—not just when it’s convenient or easy, but even when it challenges societal expectations. Being a trans ally means more than just dating trans people; it means standing with them.
What happens when you finally meet someone you deeply love and want a future with? Do you plan on keeping them separate from your life forever? At some point, keeping secrets becomes a wedge that will drive you apart. Love, in its healthiest form, thrives in the open—not in the shadows.
How to Move Forward
- Reflect on Your Fears – What’s really holding you back? Are you afraid of what your friends will say? Are you worried about how they’ll perceive you? Identifying the root of your hesitation will help you address it directly.
- Talk to Your Friends – You might be surprised at how accepting people can be when given the chance. If your friends would judge you for dating trans women, are they really the kind of people whose opinions should dictate your relationships?
- Be Honest with Future Partners – If you’re not ready to be open about who you date, you need to be upfront about that with potential partners. Let them decide if that’s something they’re okay with before investing in the relationship.
- Redefine What “Private” Means – Privacy means choosing not to share intimate details with the world. Secrecy means withholding things out of fear. If you truly care about someone, they should at least feel acknowledged in your life.
Jerry, you’re not wrong for struggling with this—it’s a journey. But you will be wrong if you continue making the transgender women you date feel like a secret. Being a true ally and a good partner means showing up, standing tall, and making it clear that who you love is nothing to be ashamed of.
I hope this helps you find clarity and the courage to move forward in a way that honors both your feelings and the dignity of the women you date.
Best, Ana
If you have a question about transgender dating or relationships, send it to Ask Ana at our contact us page. Whether you’re seeking advice, insight, or just a little reassurance, Ana is here to help navigate the complexities of love and connection in the transgender community. Stay tuned for next week’s column!
Disclaimer for Ask Ana: The Ask Ana advice column is intended for informational and discussion purposes only. Ana Marie Stelle offers guidance based on personal experience and general relationship knowledge, but her advice should not be considered professional counseling, therapy, or legal guidance. Every relationship is unique, and readers are encouraged to use their own judgment and seek professional assistance when necessary. TransVitae and Ask Ana are not responsible for any actions taken based on the advice provided. By reading this column, you acknowledge that all advice is given in good faith and should be applied with personal discretion.
