(This takes place in the US.)

I’m moving to a new city in September for graduate school. I visited the new city for a week last month and luckily landed on a place to rent starting in the fall. I found this place on Apartments.com and reached out to the landlord (also the owner) who’d posted the listing.

Turns out, he’s a single older man with a career in the news radio business. And I find him absolutely attractive.

The listing is a room for rent in a house where the owner lives. There’d be another tenant living there, plus the owner’s son who recently returned from college.

Well, we agreed to meet at his place (the house where I’ll be renting a room in). The place was nice, and he was incredible. He’s a musician, I am too. He loves art, I do too. He writes, same here. The conversation was organic and we connected so well. I felt so comfortable, I told him I was gay.

He told me that was fine, his parents had gay friends growing up so he saw it as normal. He later confessed he’s had some sexual experiences with guys before (more on that later).

That weekend we decided to seal the deal. I went over on Saturday night and brought a bottle of Whiskey as a gift. I signed the contract, and then we sat outside in the porch area, played guitar tunes for one another, and smoked cigars.

This is where I began to question whether he was trying to send me sex signals. On my previous visit, he had briefly mentioned how he didn’t want to become a “daddy” figure in terms of taking care of tenant’s responsibilities. I told him I completely understand. He made this comment again on this night, though now it was about a woman he’d been texting with.

I told him there was nothing wrong with being a daddy, to which he responded: “well, she’s not really my type anyway.” We continued our conversation on many different topics, from politics to the arts, while burning cigars and refilling our whiskey drinks.

He began to inquire about my being gay - how I’d come to find out and what my family thought of it (they’re supportive). He said people should just let others be who they are. In fact, he said that when he was younger, he thought being bi was cool and so he had tried having sex with a guy - his neighbor.

“Just one?” I inquired.

Well, two. Actually, three. He said he didn’t feel it was his thing after a while, for the rough feeling men tend to have, though he said he’s never tried anal before.

Keep in mind, by this point, we were both tipsy.

I said, “that’s interesting. I’ve tried being with women, but it wasn’t my thing. Although I am curious about being with older women. Actually, I’m attracted to older in general. 60s and above.” Hinting at my attraction to him.

The night went on, and at one point his current tenant came home. He was on the phone when he walked in, and by the sound and content of his conversation I realized the tenant was gay. I turned to the owner and asked if he would be living here in the fall, to which he responded: no. He’s currently taking your room but will be moved out by then.

Then he proceeded to ask: “why? Do you want to hook up with him? I’ll introduce you to him.” Then, jokingly, he followed up with “oh, no, he’s too young for you!”

And we laughed, and the night went on, and we nearly finished the bottle of whiskey together. Just him and I.

Sad to announce, nothing physical happened between us, other than the “manly” hug we gave each other when I left back to my hotel.

I went back the next day as I’d forgotten my umbrella, though we didn’t interact much. In that brief conversation, I’d mentioned going back home for the summer and traveling with a friend who was an ex partner whom I’d met on a gay dating app. He seemed curious about dating apps and if perhaps I knew one for heterosexuals, then said maybe “I’m still attractive even with the recent weight I’ve gained.” He rubbed his belly over his shirt.

I complimented him.

From that point on, we texted here and there though it hasn’t felt the same. Maybe, texting and being apart changes the dynamic over spending time together over glasses of whiskey.

In either case, I know that I’ve made a friend in him, but I wish I could get naked with him and make sweet love to that man.

What are your thoughts? Do I have a chance? How would you approach the situation?