My first time gay

His queer, political, adventure book, Crazy For Cuba: Notes from an Underground Traveler, is currently seeking publication. Before the Date: Set the Right Foundation

Know What You’re Looking For

Before making plans, take a moment to reflect on your true intentions:

• Are you interested in something serious or just a casual meet-up?
• Are you emotionally ready to meet someone new, or simply testing the waters?

Being upfront about your goals — especially if you met on a dating app like Grindr, Tinder, or a gay-specific platform — helps set clear expectations and reduces the risk of misunderstandings.

Choose a Comfortable, Public Spot

Opt for a location that encourages conversation and feels safe for both of you.

I sensed something different about him, so I asked him if he would like to come over to do homework together. Let identities and connections unfold in their own time — without judgment or pressure.

Stay Safe

• Share your date location with a close friend
• Meet in public for the first encounter
• Be cautious of profiles that feel vague or overly intense

Accept That Not Every Date Will Be a Perfect Match

Some first dates lead to lasting connections.

Save the ex-talk for far later (if at all).

Turning the Date into a Checklist

Sure, asking questions helps you get to know one another. I got really shaky, and I almost cried a bit, and I said, “You know how I flirt with girls? Let the conversation ebb and flow. Still haven’t come out to anyone else, because again, everyone is super religious.

A balding bearded man read his poems. Great first-date ideas include:

• A quiet coffee shop
• An LGBTQ-friendly bar or lounge
• Public spaces like parks, museums, or local markets

Your surroundings can make or break the date; a relaxed environment naturally helps keep the mood light and open.

Dress to Feel Good, Not to Impress

You don’t need to overdo it, but taking care of your appearance is key.

I was under his thumb, scared, ashamed, and aroused.

In 1964, I turned thirteen. I liked them a lot. Wishing you all the best.”

If you felt a connection and want to continue:

“Really enjoyed meeting you — I’d love to do this again soon!”

Take It One Step at a Time

Even if the date went exceptionally well, resist the urge to mentally fast-forward to your wedding day.

 series

Steve's Story - Steve tells the story of his first sexual encounter at eighteen. He came over, and sat down. Let things unfold naturally — it’s all part of the journey.

6. Extra Tips for Gay Dating Success

Avoid Making Assumptions Based on Labels

Don’t box someone in with labels like “top,” “bottom,” “masc,” or “fem.” People are multi-dimensional.

Alan invited me home. I was lucky to be in this last vestigial remnant of the Beatnik culture that was fast being swept away. He sexually teased and tormented me. But learning from the streets of Manhattan was by far the best classroom in the world.

Give yourselves space to build a genuine bond. I was also really bad at flirting because I had no actual attraction to them.) She whispered, “So, are you gay?” and I nodded and she said, “Oh my gosh, that is totally OK, that makes so much sense.” That is when the tears really started and I am so grateful for her.