Sex and the Small City

After nearly twenty years in the dating world, I had the immense joy of going on a first date that actually wasn't terrible. Okay, at almost thirty-five I should be a dating pro by now, but if I'm being totally honest, I've only been on four dates (including this one) and none of them so far have resulted in a second date. I know I'm shy and awkward when I'm out of my element, but it doesn't help that in the gay community "dating" is paramount with hooking up.

The first date that I ever went on was with a guy I wasn't attracted to. I didn't really want to go on a date with him, but I was in my early thirties and still hadn't been on a date, so I figured, beggars can't be choosers. It was obvious almost immediately -- at least to me -- that it wasn't going to go anywhere. The guy made me extremely uncomfortable, not in a scared-for-my-life kind of way, but he made me feel like I was on a job interview. He asked a lot of questions but didn't have much follow up after I'd answered them. I'm sure he's a decent guy, but we just didn't click, and that is very important.

My second date was with a slightly younger guy who lived two hours downstate. He was a Franciscan friar who worked at a museum in one of the towns I grew up in. There was great chemistry with him -- both sexual and intellectual. I was so touched that he made the four-hour round-trip drive in the winter to take me out. I really wanted things to work out with him, but he ended up moving to Ohio and we've since lost touch.

My third first date was with a guy I'd met on Grindr. We shared a love of horror movies. We met a local cafe, but he didn't end up ordering anything more than a coffee. I thought we had great chemistry, and he said I'd be hearing from him again, but he disappeared for months. We reconnected a few months ago and talked about going out again, but he's since ghosted once again. I don't take it personally because I know he has a lot of issues with anxiety and depression, and I know how hard it can be.

Max, the guy I recently went out with, is someone I've known peripherally for about a year or so now. He works at the gas station by my job, but I never saw him much. The main reason for me to even go to that gas station was to see the hot -- and tragically straight -- guy who works nights. One night I was scrolling through Grindr and I saw Max. When I had last seen him he looked like a normal guy in his mid-to-late twenties, possibly early thirties; on Grindr he had his nails painted and he had eyeliner on, as well as a heart drawn on his cheek. I figured, what the hell?

We got to talking and I found it surpisingly easy, which is interesting because I don't normally take to new people right away. I'm kind of like a cat; I have to have a while to warm up to you. We flirted and he made it clear that he did not just want casual sex. I like the idea of casual sex, but I'm far too anxious to do it, at least with strangers; a friends with benefits type situation would probably work for me, but I can't just do that with someone I barely know. We made plans to "hang" soon, but then he ghosted me.

About a month later, I found him on Grindr again and we started talking again. I had previously known that he has two young kids, but I did not know that he had two different baby mamas, nor that the newest baby mama had tried to run him over when he'd ended things with her. I'm not sure what it is about crazy women that is like honey to straight guys (Max told me on our date that it just hits different with crazy women,) but I could understand why he had flaked on me. One night, I went to see him at work, and I found him as easy to talk to in person as he was online, which is like a unicorn for me. Two hours flew by in the span of about a half hour my time.

We've continued talking since then and made plans to hang out. I didn't want to get too emotionally attached, so I asked him if our hang out was a hang out or a date; I'd rather go into it knowing where I stand so I know how much of myself to give to the situation. I was pleasantly surprised when he said he wanted it to be a date. Being a DL bi-guy who has never done anything with a guy before, I had Max pegged more as a guy who would not be comfortable with the romantic aspect of gay relationships. I figured we'd hang, mess around, and then either make it a regular thing, or he'd get freaked out and block me.

We did end up hanging out a few times prior to our date, but nothing sexual happened. As he got more comfortable with me, he became more physically intimate -- leaning on me and putting his head on my shoulder. We even kissed. When he told me he thought I was really pretty, a surge of joy burst through my body like a supernova. I wouldn't say I'm ugly by any means, but I tend to zone in more on my flaws -- my big, crooked nose, my barely there top lip, the eczema that mars the otherwise pale skin on my forehead. I figured that telling him about my clowder of cats would make him run for the hills, but shockingly he took in in stride. I couldn't help but wonder, could this guy actually be, if not The One, the one that would finally take my relationship virginity?

The day of the date I was very calm. I wore a fabulous pink and white silk Versace shirt with a pair of olive green Lagerfeld trousers. On top of black eyeliner, mascara, and blue eyeshadow, I completely my look with dangly Givenchy earrings and a diamond Givenchy necklace. Yes, I am a label queen...

Despite us having hung out already and texted nearly every day for weeks, Max was charmingly nervous about the date. I had had an IBS flare up the night before, so I opted not to eat anything; it wasn't an issue, since he'd eaten earlier. We ended up going to see The Conjuring: Last Rites and going grocery shopping. I'll admit, it's definitely a unique first date, but I don't have any complaints.

Max had never seen any of the previous The Conjuring movies, much to my chagrin, but we share a love of horror movies, so it worked out. As soon as the movie started, he took my hand in his and kissed it, before proceeding to hold my hand for the majority of the movie. When we weren't holding hands, he was resting his hand on my knee. This is normally something that would make my heart race and face flush, but for some reason, it just felt right. Knowing that Max was so nervous helped a lot, I think, at least in keeping me grounded. While he has no experience with guys at all, I at least have been on a few dates with guys and I am not virgin. I knew that we couldn't both freak out.

During our trip to the grocery store he kissed me and was holding me from behind. I'm not normally one for PDAs; I know no one wants to see people kissing and rubbing up on each other in public, regardless of their sexuality or gender identity, but once again, I found myself feeling comfortable and not caring what other people thought. At one point, some young adults were very loudly and very obviously laughing at us -- Max was wearing eyeliner, mascara, blush, and bright red lipstick as well as a black lace button up, the perfect compliment to my over-the-top Carrie Bradshaw-esque ensemble. I can only imagine what we looked like to "normal" people. Sure, it's 2025 and there has been a lot of progress in the general view of those who are different, but we are still in a small area without much culture; had we been in New York. we wouldn't have even been noticed, other than to be told how fabulous we were.

In my opinion, the best part of the date was the end, when I dropped Max off. He has full custody of his two sons, but they were with his grandmother, so there wasn't a lot of time to linger and moon over each other. He kissed me gently. I was disappointed when he broke the kiss and got out of the car. We chatted for a minute or so and then he put two fingers to his lips, kissed them, and held them out to me. "Is that all I get?" I joked, thinking he'd mumble something funny and go about his night. Instead, Max rolled his eye, leaned into the car again and kissed me passionately. Instinctively, I found my hands in his curly black hair, holding him in place so we could keep kissing. Making out has never been something that I'm particularly fond of, but with Max, I definitely don't hate it.

We've continued talking since then. He's made it clear that he would very much like to go out again. I've even gotten an invite to come over to his apartment and cuddle up on the couch while we watch his favorite anime. While it's not quite the stuff of fairytales, from a realistic perspective, I think it's more than sufficient. Unlike with the other guys, I actually look forward to seeing Max again and getting to snuggle. We have an easy comfortability with each other that is so refreshing to me.

Who knows what the future holds for us? We could end up dating, become oddly amorous friends, or we could lose touch and this will be nothing more than a blip in my dating history. No matter what happens, in the story of my life, this will go down as the best first date I've had. At this point, I'm choosing to be optimistic about where this will go and where it will take me.