Ask Anna: Feeling behind in gay dating? How to date confidently as a newly out adult
Published in Dating Advice
Dear Anna,
I'm 34 and just came out to myself (and a few close friends) as gay after years of thinking I was just "bad at dating men" or "too picky." Looking back, all the signs were there, but I genuinely thought my lack of attraction to boyfriends was normal and that romantic love was just something that happened in movies. I've spent the last decade watching my straight friends get married, buy houses and start families while I kept making excuses about why my relationships never worked out.
Now that I finally understand myself, I feel like I'm starting from absolute zero while everyone else my age has years of relationship experience under their belt. I've never been on a date with a woman, never navigated queer dating apps, and honestly don't even know basic things like who pays or how physical intimacy works between two women. I'm terrified of being that person who's 34 but acts like an awkward teenager on dates. Most women my age seem to have their lives figured out and are looking for something serious, while I feel like I need training wheels. I've been on a few dating apps but keep chickening out before actually meeting anyone because I'm so anxious about my inexperience showing.
I know I can't change my timeline, but how do I date authentically when I feel like I'm decades behind everyone else? Should I be upfront about being newly out, or will that scare people away? I'm ready to start living my truth, but I have no idea how to begin. — Not Obviously Out Beginner
Dear NOOB,
The good thing is you’re not behind. You’re not broken. Or starting from zero. You’re starting from you — and that's actually a pretty incredible place to begin.
Here's the truth that nobody talks about: Plenty of people in their 30s are figuring out dating, regardless of sexuality. Divorce exists. People leave long relationships, some of which started in their teen years. Some folks were focused on careers or caring for family. Your path to self-discovery just happened to involve a bigger plot twist than most, but that doesn't make you less worthy of love or less prepared to meet it.
The "decades behind" feeling is real, but it's also a bit of an illusion. Yes, you haven't dated women, but you've spent 34 years learning how to be in relationships with humans. You likely know how to communicate, compromise and care for someone — those skills don't suddenly disappear because the gender changed. You've probably got better emotional intelligence and self-awareness than most people who've been stumbling through dating since high school.
About being upfront: absolutely yes, but frame it positively. Instead of "I'm new and terrible at this," try "I'm recently out and excited to explore this part of myself." Many women find authenticity and enthusiasm hot. Some will swipe left because of it, yes. Others won’t care. Still others will appreciate being part of your journey — there's something beautiful about witnessing someone step into their truth, and, eventually, some sensible outdoor footwear made from recycled yoga mats.
For practical dating advice: Start slow and be kind to yourself. Video dates or coffee dates are perfect — low pressure, easy escape route if needed, cheap, and good chemistry-gaugers. As for who pays, just offer to split it or take turns (if buying drinks at a bar).
And about physical intimacy — the terrible-fun thing about any new person is that they’re new. Even if you’ve slept with a thousand people, you’ve never slept with this particular person, so you don’t know what they like, hate or how they do that thing with their elbow that drives you wild. We’re all starting from scratch with each new partner.
In fact, you might actually have an advantage here. You're approaching intimacy without a bunch of preconceived notions about what women "should" want or outdated moves you learned in college. You get to discover everything fresh, without having to unlearn bad habits or assumptions. Lucky you — you're coming to this with curiosity instead of misplaced confidence!
As to your own sexual proclivities, if you don’t know what feels good, "I'm still learning what I like" is honest and opens the door for exploration together.
While you’re at it, consider joining LGBTQ+ groups focused on activities rather than just dating. Book clubs, hiking groups, volunteer organizations — friendships often lead to connections, and you'll build community while figuring things out. Plus, you'll meet people at various stages of their own journeys.
Here's some perspective from someone who's watched countless late bloomers flourish, including my wife, who came out in her 30s: Your "inexperience" might actually be refreshing. You don't have baggage from a string of complicated queer relationships. You're no one’s gay ex! (YET.) You're approaching this with intention, which is honestly more than a lot of people bring to dating at any age. Enjoy your noob status. You only get one beginning, after all.
The woman who's right for you isn't going to care that you figured this out at 34 instead of 14. She's going to care that you're brave enough to live authentically, emotionally available, and genuinely excited to build something real together.
Stop thinking of this as catching up and start thinking of it as leveling up. You've spent three decades becoming an interesting, complex person with life experience, career skills and hopefully some decent health insurance. That's not nothing — that's actually pretty attractive.
Your journey doesn't have an expiration date, and there's no timeline for finding love. Start where you are, with who you are, right now. That's exactly enough.
©2025 Tribune Content Agency, LLC.
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